TIGER

Journal Articles: 1,000 results
Synthesis Explorer: A Chemical Reaction Tutorial System for Organic Synthesis Design and Mechanism Prediction  Jonathan H. Chen and Pierre Baldi
Synthesis Explorer is an interactive tutorial system for organic chemistry that enables students to learn chemical reactions in ways previously unrealized. Pedagogical experiments in undergraduate classes at UC Irvine indicate that the system can improve average student examination performance by ~10%.
Chen, Jonathan H.; Baldi, Pierre. J. Chem. Educ. 2008, 85, 1699.
Mechanisms of Reactions |
Reactions |
Synthesis
The Way of Synthesis. Evolution of Design and Methods for Natural Products (Tomás Hudlicky and Josephine W. Reed)  David G. J. Young
The Way of Synthesis is a 1000-page book on the progress of synthetic organic chemistry spanning its apparent inception in 1828 (Wohlers preparation of urea) to the state of the art in 2007.
Young, David G. J. J. Chem. Educ. 2008, 85, 1626.
Diastereomers |
Enantiomers |
Natural Products |
Reactions |
Stereochemistry |
Synthesis
A One-Pot, Asymmetric Robinson Annulation in the Organic Chemistry Majors Laboratory  Kiel E. Lazarski, Alan A. Rich, and Cheryl M. Mascarenhas
Describes a one-pot, enantioselective, Robinson annulation geared towards the second-year organic chemistry major and demonstrating aspects of green chemistry.
Lazarski, Kiel E.; Rich, Alan A.; Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1531.
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Gas Chromatography |
HPLC |
NMR Spectroscopy |
Synthesis |
Green Chemistry
Percy Julian, Robert Robinson, and the Identity of Eserethole  Addison Ault
The Nova production Percy JulianForgotten Genius, which included the very public disagreement over the identity of "eserethole," the key intermediate for the synthesis of the alkaloid physostigmine, left three important chemical questions unanswered.
Ault, Addison. J. Chem. Educ. 2008, 85, 1524.
Constitutional Isomers |
Enantiomers |
Natural Products |
Stereochemistry |
Synthesis
Bioorganic Chemistry: Designing Peptides with Defined Folding Properties  Caroline R. Pharr, Erik B. Hadley, and William C. Pomerantz
This Today's Science for Tomorrow's Scientists (TSTS) tutorial introduces current scientific research involving the design of molecules with well-defined folding properties, including short polymer chains of β-amino acids (β-peptides) that display antibiotic activity or form liquid crystals.
Pharr, Caroline R.; Hadley, Erik B.; Pomerantz, William C. J. Chem. Educ. 2008, 85, 1455.
Proteins / Peptides |
Receptors |
Synthesis
The First 85 Years of C-Nitroso Compounds: A Survey of the Salient Features  Brian G. Gowenlock and George B. Richter-Addo
The development of the structural chemistry of C-nitroso compounds, the colors of which have long fascinated researchers, illustrates the interplay of theory and experiment throughout the period 18741959.
Gowenlock, Brian G.; Richter-Addo, George B. J. Chem. Educ. 2008, 85, 1243.
Descriptive Chemistry |
Molecular Properties / Structure |
Synthesis
Determination of Phosphates by the Gravimetric Quimociac Technique  Lee Alan Shaver
The determination of phosphates by the classic quimociac gravimetric technique is well-known for its precision and accuracy and has the advantages of producing a predictable, stable, high molar mass precipitate that students find easy to form, filter, dry, and weigh.
Shaver, Lee Alan. J. Chem. Educ. 2008, 85, 1097.
Applications of Chemistry |
Gravimetric Analysis |
Quantitative Analysis |
Synthesis
Developing and Disseminating NOP: An Online, Open-Access, Organic Chemistry Teaching Resource To Integrate Sustainability Concepts in the Laboratory  Johannes Ranke, Müfit Bahadir, Marco Eissen, and Burkhard König
Describes a project that identifies parameters for sustainable practices in organic chemistry laboratories, including the atom economy and energy efficiency of chemical transformations, questions of waste and renewable feedstocks, toxicity and ecotoxicity, and safety measures.
Ranke, Johannes; Bahadir, Müfit; Eissen, Marco; König, Burkhard. J. Chem. Educ. 2008, 85, 1000.
Green Chemistry |
Synthesis |
Toxicology
Modification to Synthesis of Methyl Diantilis  William H. Miles
After we published the Synthesis of Methyl Diantilis, a Commercially Important Fragrance,we encountered a problem with the catalyst, Amberlyst-15, used in the second step. A revised laboratory procedure has replaced the original supplement available at JCE Online.
Miles, William H. J. Chem. Educ. 2008, 85, 917.
Catalysis |
Synthesis |
Laboratory Equipment / Apparatus
Polymer-Supported Reagents and 1H–19F NMR Couplings: The Synthesis of 2-Fluoroacetophenone  Nicola Pohl and Kimberly Schwarz
Describes an experiment in which 2-bromoacetophenone is converted to 2-fluoroacetophenone using a solid-phase nucleophilic fluorine source. The experiment introduces students to the utility of solid-phase reagents in organic synthesis, to NMR-active nuclei other than 1H without the requirement of a special NMR probe, and to the unique uses of fluorine in molecular design.
Pohl, Nicola; Schwarz, Kimberly. J. Chem. Educ. 2008, 85, 834.
Aldehydes / Ketones |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
Organic Synthesis: Strategy and Control (Paul Wyatt and Stuart Warren)  Richard Pagni
Organic Synthesis is an excellent resource on organic synthesis. Because of the enormous breadth and complexity of the subject, being able to organize the material into coherent units as well as interconnecting them into a coherent whole is key to writing a successful book on organic synthesis. Wyatt and Warren show this skill in abundance.
Pagni, Richard. J. Chem. Educ. 2008, 85, 785.
Synthesis |
Mechanisms of Reactions
Stereochemical Control in Carbohydrate Chemistry  Rhys Batchelor, Peter T. Northcote, Joanne E. Harvey, Emma M. Dangerfield, and Bridget L. Stocker
Describes a sequence of experiments that leads students from the derivatization of naturally occurring D-glucose through to the formation of simple alkyl and aryl glycosides. In doing so, this experiment provides an overview of glycoside synthesis with a focus on the control of stereochemistry at the anomeric center and structural elucidation through NMR spectroscopy.
Batchelor, Rhys; Northcote, Peter T.; Harvey, Joanne E.; Dangerfield, Emma M.; Stocker, Bridget L. J. Chem. Educ. 2008, 85, 689.
Carbohydrates |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Synthesis and Symmetry of Two Cobalt(III) Complexes with Tetradentate Ligands  Mark McClure
In this laboratory exercise, students synthesize two series of cobalt(III) complexes. Although the two resulting ligands have the same chemical formula, one is linear and the other is branched, giving rise to complexes with different symmetries that are examined through the use of 13C NMR spectroscopy.
McClure, Mark. J. Chem. Educ. 2008, 85, 420.
Coordination Compounds |
NMR Spectroscopy |
Synthesis
A Three-Step Laboratory Sequence To Prepare a Carbene Complex of Silver(I) Chloride  John P. Canal, Taramatee Ramnial, Lisa D. Langlois, Colin D. Abernethy, and Jason A. C. Clyburne
Presents a multistep inorganic synthesisof N-heterocyclic carbenes that introduces students to modern organometallic chemistry, multinuclear NMR (1H and 13C) spectroscopy, and novel coordination geometries and valence states of carbon.
Canal, John P.; Ramnial, Taramatee; Langlois, Lisa D.; Abernethy, Colin D.; Clyburne, Jason A. C. J. Chem. Educ. 2008, 85, 416.
Coordination Compounds |
NMR Spectroscopy |
Organometallics |
Synthesis
Synthesis of Diapocynin  Mina S. Dasari, Kristy M. Richards, Mikaela L. Alt, Clark F. P. Crawford, Amanda Schleiden, Jai Ingram, Abdel Aziz Amadou Hamidou, Angela Williams, Patricia A. Chernovitz, Rensheng Luo, Grace Y. Sun, Ron Luchtefeld, and Robert E. Smith
Diapocynin is synthesized by the oxidative coupling of apocynin and analyzed by FTIR, 1H NMR, and negative ion atmospheric pressure chemical ionization LCMS.
Dasari, Mina S.; Richards, Kristy M.; Alt, Mikaela L.; Crawford, Clark F. P.; Schleiden, Amanda; Ingram, Jai; Hamidou, Abdel Aziz Amadou; Williams, Angela; Chernovitz, Patricia A.; Luo, Rensheng; Sun, Grace Y.; Luchtefeld, Ron; Smith, Robert E. J. Chem. Educ. 2008, 85, 411.
Drugs / Pharmaceuticals |
HPLC |
Mass Spectrometry |
Phenols |
Synthesis
Natural Product Chemistry at a Glance (Stephen P. Stanforth)  Alan M. Rosan
This sleek, purposeful, and authoritative book is designed to present to undergraduates the structural variety and biosynthetic pathways of the main classes of natural products. It does this admirably by stating and continually reinforcing fundamental organic and bioorganic structural and functional principles.
Rosan, Alan M. J. Chem. Educ. 2008, 85, 203.
Natural Products |
Synthesis
A Simple Assignment That Enhances Students' Ability To Solve Organic Chemistry Synthesis Problems and Understand Mechanisms  Jennifer Teixeira and R. W. Holman
Describes an original, easily implemented approach in which students construct a "functional group transformation" notebook which helps them to think about organic reactions in both the forward and the reverse (retrosynthetic) sense.
Teixeira, Jennifer; Holman, Robert W. J. Chem. Educ. 2008, 85, 88.
Mechanisms of Reactions |
Synthesis |
Student-Centered Learning
Manipulation of a Schlenk Line: Preparation of Tetrahydrofuran Complexes of Transition-Metal Chlorides  Craig M. Davis and Kelly A. Curran
This exercise introduces students to handling air-sensitive materials using Schlenk techniques in the synthesis of anhydrous tetrahydrofuran complexes of transition-metal chlorides.
Davis, Craig M.; Curran, Kelly A. J. Chem. Educ. 2007, 84, 1822.
Coordination Compounds |
Synthesis |
Transition Elements
The Synthetic Organic Chemist's Companion (Michael C. Pirrung)  Justin Carson Reno
The Synthetic Organic Chemists Companion takes a chemist through the typical synthetic chemistry process. Each step, from locating reagents to cleaning up after structure elucidation, is described in a succinct yet informative manner.
Reno, Justin Carson. J. Chem. Educ. 2007, 84, 1766.
Synthesis
From the Research Bench to the Teaching Laboratory: Gold Nanoparticle Layering  Maria Oliver-Hoyo and Ralph W. Gerber
The procedures presented here involve the synthesis of gold colloidal suspensions, attachment of a functional group to glass with subsequent creation of self-assembled monolayers through deposition of gold nanoparticles, and measurements of wavelengths, absorbance, and conductivity.
Oliver-Hoyo, Maria; Gerber, Ralph W. J. Chem. Educ. 2007, 84, 1174.
Nanotechnology |
Surface Science |
Synthesis |
UV-Vis Spectroscopy
On the Use of "Green" Metrics in the Undergraduate Organic Chemistry Lecture and Lab To Assess the Mass Efficiency of Organic Reactions  John Andraos and Murtuzaali Sayed
This article describes a novel approach to evaluate the complete reaction mass efficiency and raw material cost of any chemical transformation using an Excel spreadsheet.
Andraos, John; Sayed, Murtuzaali. J. Chem. Educ. 2007, 84, 1004.
Green Chemistry |
Synthesis
Synthesis of Plant Auxin Derivatives and Their Effects on Ceratopteris richardii  Corey E. Stilts and Roxanne Fisher
In this experiment, organic chemistry students synthesize derivatives of their own design of the plant auxins indole-3-acetic acid and 1-naphthalene acetic acid. Biochemistrycell biology students then examine the development of Ceratopteris richardii gametophytes on medium containing auxin derivatives synthesized in the organic chemistry lab.
Stilts, Corey E.; Fisher, Roxanne. J. Chem. Educ. 2007, 84, 999.
Biological Cells |
Bioorganic Chemistry |
Hormones |
Synthesis
A New Perspective on the Structure of Chemistry as a Basis for the Undergraduate Curriculum  Martin J. Goedhart
This article make a distinction between three context areas of chemistry and their related rationalesanalysis, synthesis, and theory developmentand argues that dividing chemistry into these three areas can be used to design a new curriculum.
Goedhart, Martin J. J. Chem. Educ. 2007, 84, 971.
Synthesis
Improved Synthesis of Geodken's Macrocycle through the Synthesis of the Dichloride Salt  J. H. Niewahner, Keith A. Walters, and Ashley Wagner
Describes improvements to the synthesis of Geodken's macrocycle, H2C22H22N4, (5,14-dihydro-6,8,15,17- tetramethyldibenzo[b,i]-[1,4,8,11] tetraazacyclotetradecahexane).
Niewahner, J. H.; Walters, Keith A.; Wagner, Ashley. J. Chem. Educ. 2007, 84, 477.
Coordination Compounds |
Reactions |
Synthesis
Spectral Characterization of a Novel Luminescent Organogel  Yan Waguespack and Shawn R. White
Describes an experiment in which chemistry majors taking physical chemistry or instrumental analysis during their third or fourth year synthesize a novel luminescent organogel. Students are exposed to various topics in spectroscopy such as the acquisition of excitation and emission spectra, luminescence, quenching, and SternVolmer plots.
Waguespack, Yan; White, Shawn R. J. Chem. Educ. 2007, 84, 333.
Spectroscopy |
Synthesis
Manual Solid–Phase Peptide Synthesis of Metallocene–Peptide Bioconjugates  Srecko I. Kirin, Fozia Noor, Nils Metzler-Nolte, and Water Mier
Describes a simple procedure for the manual solid-phase synthesis of peptides in which a variety of markers can be attached to the N-terminus.
Kirin, Srecko I.; Noor, Fozia; Metzler-Nolte, Nils; Mier, Water. J. Chem. Educ. 2007, 84, 108.
Bioorganic Chemistry |
Organometallics |
Proteins / Peptides |
Synthesis
A Research-Based Laboratory Course in Organic Chemistry  Thomas A. Newton, Henry J. Tracy, and Caryn Prudenté
Describes the development, implementation, evolution, and evaluation of a unique approach to laboratory instruction in organic chemistry. The new course involves a combinatorial strategy that offers every student a different group of 14 metallole as their personal synthetic target.
Newton, Thomas A.; Tracy, Henry J.; Prudenté, Caryn. J. Chem. Educ. 2006, 83, 1844.
Combinatorial Chemistry |
Organometallics |
Synthesis |
Undergraduate Research
A New Model for Transitioning Students from the Undergraduate Teaching Laboratory to the Research Laboratory. The Evolution of an Intermediate Organic Synthesis Laboratory Course  Jessica J. Hollenbeck, Emily N. Wixson, Grant D. Geske, Matthew W. Dodge, T. Andrew Tseng, Allen D. Clauss, and Helen E. Blackwell
Outlines the transformation of an intermediate undergraduate organic synthesis laboratory course to provide experience using modern experimental techniques and chemical information resources, instruction in scientific writing and the use of chemical drawing software, and an awareness of basic scientific ethics.
Hollenbeck, Jessica J.; Wixson, Emily N.; Geske, Grant D.; Dodge, Matthew W.; Tseng, T. Andrew; Clauss, Allen D.; Blackwell, Helen E. J. Chem. Educ. 2006, 83, 1835.
Professional Development |
Synthesis |
Undergraduate Research |
Ethics
Asymmetric Aldol Reaction Induced by Chiral Auxiliary  Jorge Pereira and Carlos A. M. Afonso
Describes an asymmetric aldol reaction based on the use of (4R,5S)-1,5-dimethyl-4-phenylimidazolidin- 2-one as a chiral auxiliary in a three-step procedure.
Pereira, Jorge; Afonso, Carlos A. M. J. Chem. Educ. 2006, 83, 1333.
Aldehydes / Ketones |
Asymmetric Synthesis |
Chirality / Optical Activity |
Diastereomers |
NMR Spectroscopy |
Chromatography |
Synthesis |
Stereochemistry
Two-Cycle Organic Chemistry and the Student-Designed Research Lab  Dennis J. Gravert
Teaching a two-semester, lecture and laboratory course in organic chemistry using the "two-cycle" strategy offers several advantages over a traditionally organized course.
Gravert, Dennis J. J. Chem. Educ. 2006, 83, 898.
Synthesis |
Undergraduate Research |
Student-Centered Learning
Incorporation of Microwave Synthesis into the Undergraduate Organic Laboratory  Alan R. Katritzky, Chunming Cai, Meghan D. Collins, Eric F. V. Scriven, Sandeep K. Singh, and E. Keller Barnhardt
Describes a simple way to effectively implement microwave synthesis into the undergraduate organic laboratory curriculum.
Katritzky, Alan R.; Cai, Chunming; Collins, Meghan D.; Scriven, Eric F. V.;Singh, Sandeep K.; Barnhardt, E. Keller. J. Chem. Educ. 2006, 83, 634.
Aromatic Compounds |
Laboratory Equipment / Apparatus |
Reactions |
Synthesis
Microwave-Assisted Heterocyclic Chemistry for Undergraduate Organic Laboratory  Robert Musiol, Bozena Tyman-Szram, and Jaroslaw Polanski
Microwave-assisted techniques are used to design new environmentally benign syntheses of heterocycles for the undergraduate organic laboratory.
Musiol, Robert; Tyman-Szram, Bozena; Polanski, Jaroslaw. J. Chem. Educ. 2006, 83, 632.
Green Chemistry |
Heterocycles |
Reactions |
Synthesis
Preparation and Viscosity of Biodiesel from New and Used Vegetable Oil. An Inquiry-Based Environmental Chemistry Laboratory  Nathan R. Clarke, John Patrick Casey, Earlene D. Brown, Ezenwa Oneyma, and Kelley J. Donaghy
Presents a simple synthetic laboratory that requires students to find a general synthetic method to make biodiesel (fuel made from clean sources such as vegetable oils) and assess its viscosity versus temperature.
Clarke, Nathan R.; Casey, John Patrick; Brown, Earlene D.; Oneyma, Ezenwa; Donaghy, Kelley J. . J. Chem. Educ. 2006, 83, 257.
Applications of Chemistry |
Esters |
Physical Properties |
Synthesis
2005 Nobel Prize in Chemistry. Development of the Olefin Metathesis Method in Organic Synthesis  Charles P. Casey
This article tells the story of how olefin metathesis became a truly useful synthetic transformation and a triumph for mechanistic chemistry, and illustrates the importance of fundamental research.
Casey, Charles P. J. Chem. Educ. 2006, 83, 192.
Synthesis
A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone  John J. Esteb, J. Nathan Hohman, Diana E. Schlamadinger, and Anne M. Wilson
The BaeyerVilliger reaction provides an efficient method to convert ketones to esters or lactones. In this experiment, m-chloroperoxybenzoic acid and 4-tert-butylcyclohexanone are mixed together for under solvent-free conditions to produce ?-t-butyl-e-caprolactone.
Esteb, John J.; Hohman, J. Nathan; Schlamadinger, Diana E.; Wilson, Anne M. J. Chem. Educ. 2005, 82, 1837.
Green Chemistry |
Synthesis |
Esters |
Oxidation / Reduction
Strategic Applications of Named Reactions in Organic Synthesis: Background and Detailed Mechanisms (László Kürti and Barbara Czakó)  R. W. Holman
Krti and Czak use a two-page format that uses four-color graphics to address 250 reactions selected for inclusion based upon their applicability to modern natural products synthesis. Each named reaction is concisely introduced, mechanistically explained, and then set in context with example applications involving the production of natural products.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Name Reactions and Reagents in Organic Synthesis, 2nd Edition (Bradford P. Mundy, Michael G. Ellerd, and Frank G. Favaloro)  R. W. Holman
Name Reactions and Reagents in Organic Synthesis is an exhaustive collection, addressing more than 500 reactions (and rearrangements). The breadth of coverage extends well beyond the confines of a typical undergraduatebeginning graduate organic chemistry course, although the detail presented for each reaction is minimal.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)  R. W. Holman
Named Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Named Organic Reactions, 2nd Edition (Thomas Laue and Andreas Plagens)  R. W. Holman
Named Organic Reactions is a collection of 134 of the most common named organic reactions, with common being defined as those reactions most likely addressed in the combination of a typical sophomore organic chemistry sequence plus an advanced undergraduatebeginning graduate organic reactions and synthesis course.
Holman, R. W. J. Chem. Educ. 2005, 82, 1780.
Synthesis |
Mechanisms of Reactions
Interlaboratory Collaborations in the Undergraduate Setting  Elise G. Megehee, Alison Hyslop, and Richard J. Rosso
We have developed a novel approach for undergraduate laboratory education termed "interlaboratory collaboration" in which students in distinct laboratory courses are responsible for different aspects of a single project that spans these courses. This approach attempts to model the industrial workplace where separate groups are responsible for different aspects of a project. By having students synthesize or study a set of different compounds the students within a class can compare their data and investigate trends in chemical reactivity or physical properties.
Megehee, Elise G.; Hyslop, Alison; Rosso, Richard J. J. Chem. Educ. 2005, 82, 1345.
Industrial Chemistry |
Synthesis
Using Building-Block Puzzles To Practice Drawing Organic Mechanisms  Ender Erdik
This pencil-and-paper activity is designed to test the ability of students in writing intermediates and products in the reactions of ketones. An undergraduate student who is successful in organic chemistry at the sophomore level is expected to fill in empty boxes with the appropriate "building blocks", which are atoms and atom groups (neutral or ionic). Solving the puzzle will give the formulas of reactants, reactive intermediates, and products. Students test their understanding of reaction mechanisms while having fun.
Erdik, Ender. J. Chem. Educ. 2005, 82, 1325.
Reactive Intermediates |
Synthesis |
Aldehydes / Ketones |
Mechanisms of Reactions
Use of Enzymes in Organic Synthesis: Reduction of Ketones by Baker's Yeast Revisited  James Patterson and Snorri Th. Sigurdsson
The undergraduate organic laboratory Bakers Yeast Reduction of Ethyl Acetoacetate has been improved in two different ways. First, the addition of small quantities of hexane to the aqueous yeast system along with an improved workup protocol has dramatically increased the yield and reproducibility of the ketone conversion to the corresponding alcohol with a high enantiomeric excess. Second, the enantiomeric excess of the alcohol product was ascertained by coupling the alcohol mixture with a chiral acid and analyzing the resulting mixture of diastereomeric esters by proton NMR.
Patterson, James; Sigurdsson, Snorri Th. J. Chem. Educ. 2005, 82, 1049.
Enzymes |
NMR Spectroscopy |
Stereochemistry |
Gas Chromatography |
Synthesis
A Convenient Method for Dispensing Organometallic Reagents  Thomas A. Newton
The construction of a simple apparatus for dispensing air-sensitive organometallic reagents is described.
Newton, Thomas A. J. Chem. Educ. 2005, 82, 936.
Organometallics |
Instrumental Methods |
Synthesis
Supercritical Fluid Facilitated Growth of Copper and Aluminum Oxide Nanoparticles  Geoffrey L. Williams, Jason K. Vohs, Jonathan J. Brege, and Bradley D. Fahlman
Though the diversity of applications involving supercritical fluids (SCFs) continue to mount in virtually every sector of the scientific workplace, this environmentally-friendly medium is only briefly mentioned in undergraduate curricula; most often without hands-on laboratory experience. A new experimental module featuring this technology was introduced into an undergraduate inorganic chemistry laboratory.
Williams, Geoffrey L.; Vohs, Jason K.; Brege, Jonathan J.; Fahlman, Bradley D. J. Chem. Educ. 2005, 82, 771.
Synthesis |
Materials Science |
Nanotechnology
Preparation of Dppe-Stabilized Gold Nanoparticles  Keenan E. Dungey, David P. Muller, and Tammy Gunter
This laboratory experiment is designed to give upper-level undergraduate students experience in nanotechnology by synthesizing and characterizing gold nanoparticles. The two-to-four week project begins with the synthesis of the ligand, 1,2-bis(diphenylphosphino)ethane (dppe). Students then use the dppe to prepare gold nanoparticles. The products are analyzed by IR and NMR spectroscopies and comparisons are made between the bound and unbound ligand.
Dungey, Keenan E.; Muller, David P.; Gunter, Tammy. J. Chem. Educ. 2005, 82, 769.
Synthesis |
Main-Group Elements |
Materials Science |
Nanotechnology
Combined 31P and 1H NMR Experiments in the Structural Elucidation of Polynuclear Thiolate Complexes  Elena Cerrada and Mariano Laguna
The use of diphosphines such as bis(diphenylphosphine)ethane (dppe) or bis(diphenylphosphine)methane (dppm) with dithiolate gold(I) derivatives induces the isolation of dithiolate gold(I) complexes with two different structures and stoichiometries depending on the diphosphine: [Au2(-dppe)(1,2-S2C6H4)] and [Au4(dppm)2(1,2-S2C6H4)2], respectively. Such structures and stoichiometries can be determined by NMR experiments, not only 1H NMR and 31P{1H} NMR, but also 1H{31P}NMR experiments.
Cerrada, Elena; Laguna, Mariano. J. Chem. Educ. 2005, 82, 630.
NMR Spectroscopy |
Synthesis
Synthesis of an Epoxide Carbonylation Catalyst: Exploration of Contemporary Chemistry for Advanced Undergraduates  Yutan D.Y.L. Getzler, Joseph A.R. Schmidt, and Geoffrey W. Coates
This lab presents an opportunity for advanced students of organic or inorganic chemistry to prepare a compound that belongs to a recently introduced class of catalyst that are active for the carbonylation of epoxides and related substrates to -lactones and related products. Epoxides are inexpensive and readily available while -lactones are not and have broad utility in both small molecule and polymer synthesis. Consequently, these catalysts, and related systems, have been the subject of intense investigation recently.
Getzler, Yutan D.Y.L.; Schmidt, Joseph A.R.; Coates, Geoffrey W. J. Chem. Educ. 2005, 82, 621.
Catalysis |
Synthesis |
Organometallics |
Undergraduate Research |
Epoxides
Synthesis of Meso-Octamethylporphyrinogen: An Undergraduate Laboratory Mini-Scale Experiment in Organic Heterocyclic Chemistry  Abilio J.F.N. Sobral
In this laboratory experiment, students synthesize and investigate the properties of a stable porphyrinogen. Porphyrinogens are an important class of porphyrin precursors as well as important macrocycles for the preparation of coordination compounds. The acid-catalyzed cyclization of pyrrole and acetone uses common, inexpensive reagents to afford the meso-octamethylporphyrinogen in a near-analytical grade in one step, directly from the reaction medium.
Sobral, Abilio J.F.N. J. Chem. Educ. 2005, 82, 618.
Synthesis |
Microscale Lab |
Heterocycles
Fifty Ways To Make Boric Acid (with Apologies to Paul Simon)  Craig M. Davis
Many graduate students whose projects are centered on the synthesis of novel compounds know too well the frustration of failed reactions. For me, the dry spells lasted several months at a stretch. Inspired by Paul Simons song Fifty Ways to Leave Your Lover, I penned a poem summarizing my experiences, which I bound at the end of my personal copy of my dissertation.
Davis, Craig M. J. Chem. Educ. 2005, 82, 541.
Acids / Bases |
Synthesis
Polymers (Oxford Chemistry Primers No. 85) (David Walton and J. Phillip Lorimer)  John H. Shibata
Although the title suggests a broad, general coverage of polymers, in reality this book focuses primarily on synthesis and the macroscopic properties of polymers. A significant portion of the book emphasizes practical considerations of polymerscommercial aspects determined by the properties of polymers and the industrial processes for polymer synthesis and three-dimensional network formation. In many cases, specific polymer types and materials are described in detail. The concreteness of explicit examples to illustrate the principles of polymerization and the properties of networks and functional polymers are appropriate for readers seeking a practical introduction to polymers.
Shibata, John H. J. Chem. Educ. 2005, 82, 533.
Polymerization |
Synthesis
Environmental Problems and New Hope for the Treatment of Malaria  Sabine Heinhorst and Gordon C. Cannon
Articles from Nature that deal with environmental problems and treatment of malaria are described.
Heinhorst, Sabine; Cannon, Gordon C. J. Chem. Educ. 2005, 82, 186.
Drugs / Pharmaceuticals |
Synthesis
Solvent-Free Conversion of α-Naphthaldehyde to 1-Naphthoic Acid and 1-Naphthalenemethanol: Application of the Cannizzaro Reaction  John J. Esteb, Keith M. Gligorich, Stacy A. O'Reilly, and Jeremy M. Richter
The Cannizzaro reaction is routinely covered in organic textbooks, but owing to the shortage of suitable procedures for the undergraduate teaching laboratory, this reaction is seldom performed in a first-year organic chemistry class. In this experiment, powdered potassium hydroxide and a-naphthaldehyde are heated under solvent-free conditions to produce 1-naphthoic acid and 1-naphthalenemethanol in 86% and 79% yields, respectively. The solvent-free nature of this procedure greatly reduces the quantity of waste generated by students relative to the typical solvent-based method of preparation.
Esteb, John J.; Gligorich, Keith M.; O'Reilly, Stacy A.; Richter, Jeremy M. J. Chem. Educ. 2004, 81, 1794.
Green Chemistry |
Synthesis
Radical Reactions in Organic Synthesis (Oxford Chemistry Masters) (Samir Z. Zard)  R. David Crouch

Crouch, R. David. J. Chem. Educ. 2004, 81, 1718.
Synthesis
Integration of Computational and Preparative Techniques To Demonstrate Physical Organic Concepts in Synthetic Organic Chemistry: An Example Using Diels–Alder Reactions  David R. J. Palmer
Preparative experiments in organic chemistry rarely invoke physical organic principles explicitly, even at the intermediate level where these principles are taught. Computational exercises often address such topics as molecular orbital theory and reaction energetics, but may not allow students to make the conceptual leap from computer to flask. The experiment described, based on endoexo selectivity of DielsAlder reactions, bridges this gap by integrating computational and preparative experiments.
Palmer, David R. J. J. Chem. Educ. 2004, 81, 1633.
Computational Chemistry |
Synthesis |
Molecular Modeling
Parallel Combinatorial Synthesis of Azo Dyes: A Combinatorial Experiment Suitable for Undergraduate Laboratories  Benjamin W. Gung and Richard T. Taylor
A parallel combinatorial synthesis of azo dyes experiment was developed that uses distinct colors to illustrate the concept of diversity and structurefunction relationships. This experiment is suitable for undergraduate laboratories and has been used by both chemistry majors and nonmajors undergraduates in Miami University. Azo dyes can be prepared easily in one laboratory period and were chosen to illustrate the concept of diversity oriented synthesis. In the experiment, the positions of the laboratory are divided into a grid. Each student produces a unique azo dye, whose structure is coded according to his or her lab bench position.
Gung, Benjamin W.; Taylor, Richard T. J. Chem. Educ. 2004, 81, 1630.
Combinatorial Chemistry |
Dyes / Pigments |
Synthesis
Combinatorial Partial Hydrogenation Reactions of 4-Nitroacetophenone. An Undergraduate Organic Laboratory  Kevin W. Kittredge, Susan S. Marine, and Richard T. Taylor
A combinatorial organic chemistry experiment that utilizes an inexpensive commercially available parallel reactor, Argonaut's FirstMate, is described. Students perform a metal catalyzed partial hydrogenation reaction on a multi-functionalized substrate and analyze product ratios by GCMS. Students evaluate a simple organic reaction that yields four different products. The reactions are performed in the presence and absence of a reaction modifier, methanesulfonic acid. Differing product ratios are obtained with the different types of metal catalysts and with the presence or the absence of the reaction modifier.
Kittredge, Kevin W.; Marine, Susan S.; Taylor, Richard T. J. Chem. Educ. 2004, 81, 1494.
Catalysis |
Combinatorial Chemistry |
Synthesis |
Reactions
The Conversion of Carboxylic Acids to Ketones: A Repeated Discovery  John W. Nicholson and Alan Wilson
This article describes the history of the reaction converting carboxylic acids to ketones. The reaction has been rediscovered several times, yet has actually been known for centuries.
Nicholson, John W.; Wilson, Alan. J. Chem. Educ. 2004, 81, 1362.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones
Competition Experiments as a Means of Evaluating Linear Free Energy Relationships. An Experiment for the Advanced Undergraduate Organic Chemistry Lab   Richard J. Mullins, Andrei Vedernikov, and Rajesh Viswanathan
A novel approach to exploring Hammett relationships in the undergraduate teaching lab is described. The use of competition experiments proved to be a reliable method for the construction of Hammett plots with good correlation. Reactions that were studied include the sodium borohydride reduction, methylmagnesium bromide addition, and oxime formation with para-substituted acetophenones. The composition of reaction mixtures was established by 1H NMR integrations. The use of competition experiments ensured consistency in the results, as relatively little control was required over the reaction conditions.
Mullins, Richard J.; Vedernikov, Andrei; Viswanathan, Rajesh. J. Chem. Educ. 2004, 81, 1357.
Kinetics |
Mechanisms of Reactions |
NMR Spectroscopy |
Synthesis
Scaling Up Effects in the Organic Laboratory  Anna Persson and Ulf M. Lindström
A simple, yet safe and effective set of experiments to expose chemistry students to some of the effects that may be encountered when scaling up an organic reaction is described. The exothermic DielsAlder reaction between maleic anhydride and cyclopentadiene was found to be ideal for our purposes and was performed in small, medium, and large scale for comparison. The observed differences of heat evolution between the three scales were significant. Also, to demonstrate how excess heat evolution can be controlled by simple means, two additional experiments in which the reaction was run either with small glass helices or water present were performed.
Persson, Anna; Lindström, Ulf M. J. Chem. Educ. 2004, 81, 1353.
Industrial Chemistry |
Synthesis |
Laboratory Management
Electrophilic Anti Addition of Bromine to 2-Methylbut-2–ene with the N-Methylpyrrolidin-2-one Hydrotribromide Complex   Jean-François Berrien, Olivier Provot, Delphine Joseph, and Alain Bekaert
The reaction of N-methylpyrrolidin-2-one hydrotribromide complex (MPHT) with 2-methylbut-2-ene has been investigated. This compound proved to be a successful substitute of the dangerous molecular bromine used for bromination of olefins. It is a stable complex, not corrosive, not necrosing, nor moisture sensitive. Moreover, it has been shown that it is far less toxic than bromine, and therefore much easier for students to handle.
Berrien, Jean-François; Provot, Olivier; Joseph, Delphine; Bekaert, Alain. J. Chem. Educ. 2004, 81, 1348.
Synthesis
Regioselective Synthesis of a Stereodefined Heterocyclic Push–Pull Alkene. 1H NMR Studies and Two-Dimensional TLC Illustrating Z/E Isomerization  Rade Markovi, Marija Baranac, Vesna Jovanovi, and Zdravko Dambaski
Facile and direct regioselective synthesis of the 4-oxothiazolidine derivative from inexpensive chemicals as an example of kinetic versus thermodynamic control is described.
Markovi, Rade; Baranac, Marija; Jovanovi, Vesna; Dambaski, Zdravko. J. Chem. Educ. 2004, 81, 1026.
Heterocycles |
Alkenes |
Stereochemistry |
Synthesis |
NMR Spectroscopy
Benzoin Condensation: Monitoring a Chemical Reaction by High-Pressure Liquid Chromatography  Apurba Bhattacharya, Vikram C. Purohit, and Nicholas R. Beller
High-pressure liquid chromatography was successfully introduced in the undergraduate advanced organic chemistry laboratory to reinvestigate the cyanide-catalyzed condensation of benzaldehyde to benzoin.
Bhattacharya, Apurba; Purohit, Vikram C.; Beller, Nicholas R. J. Chem. Educ. 2004, 81, 1020.
HPLC |
Chromatography |
Quantitative Analysis |
Synthesis |
Instrumental Methods
Simple Epoxide Formation for the Organic Laboratory Using Oxone  William C. Broshears, John J. Esteb, Jeremy Richter, and Anne M. Wilson
This experiment demonstrates a simple synthesis of an epoxide and formation of a secondary oxidizing agent.
Broshears, William C.; Esteb, John J.; Richter, Jeremy; Wilson, Anne M. J. Chem. Educ. 2004, 81, 1018.
Oxidation / Reduction |
Synthesis
Spectroscopic Properties of Some Simple Esters. A Practical Application of Synthesis and Spectroscopy in the Undergraduate Organic Laboratory  David P. Brown, Haris Durutlic, and Didier Juste
This exercise, the synthesis and spectroscopic analysis of the allyl esters of some aromatic carboxylic acids, consists of a series of open-ended experiments.
Brown, David P.; Durutlic, Haris; Juste, Didier. J. Chem. Educ. 2004, 81, 1016.
Esters |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Chromatography
Synthesis of Chemiluminescent Esters: A Combinatorial Synthesis Experiment for Organic Chemistry Students  Robert Duarte, Janne T. Nielsen, and Veljko Dragojlovic
In this laboratory exercise, a peroxyoxalate chemiluminescence experiment has been integrated with a combinatorial synthesis experiment.
Duarte, Robert; Nielsen, Janne T.; Dragojlovic, Veljko. J. Chem. Educ. 2004, 81, 1010.
Esters |
Synthesis |
Molecular Properties / Structure
Incorporation of Medicinal Chemistry into the Organic Chemistry Curriculum  David C. Forbes
An optional exercise designed for students enrolled in the lecture component of organic chemistry is described. This exercise, designed for students at the sophomore level, focuses on a drug of medicinal relevance.
Forbes, David C. J. Chem. Educ. 2004, 81, 975.
Medicinal Chemistry |
Synthesis
One-Pot Synthesis of 7-Hydroxy-3-carboxycoumarin in Water  Francesco Fringuelli, Oriana Piermatti, and Ferdinando Pizzo
The procedure highlights the advantages of using an aqueous medium, particularly the possibility of controlling the pH and isolating the reaction product without using any organic solvent.
Fringuelli, Francesco; Piermatti, Oriana; Pizzo, Ferdinando. J. Chem. Educ. 2004, 81, 874.
Green Chemistry |
Aqueous Solution Chemistry |
Synthesis |
Heterocycles
The Synthesis and Isolation of N-tert-Butyl-2-phenylsuccinamic Acid and N-tert-Butyl-3-phenylsuccinamic Acid. An Undergraduate Organic Chemistry Laboratory Experiment  Victor Cesare, Ishwar Sadarangani, Janet Rollins, and Dennis Costello
This experiment, which demonstrates that two isomeric products are obtained when an unsymmetrical anhydride is reacted with a nucleophile and that these isomers are easily separated based on their difference in acidity, is useful in introducing the topic of carboxylic acid derivatives into the organic chemistry laboratory.
Cesare, Victor; Sadarangani, Ishwar; Rollins, Janet; Costello, Dennis. J. Chem. Educ. 2004, 81, 713.
Synthesis |
Chirality / Optical Activity |
NMR Spectroscopy
The Electrophilic Aromatic Substitution of Fluorobenzene   Addison Ault
Joel Rosenthal and David Schuster published a paper entitled The Anomalous Reactivity of Fluorobenzene in Electrophilic Aromatic Substitution and Related Phenomena. The authors and the reviewers, apparently, were not aware of my publication in this Journal in 1966 entitled The Activating Effect of Fluorine in Electrophilic Aromatic Substitution.
Ault, Addison. J. Chem. Educ. 2004, 81, 644.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
Cautionary Comments   R. G. Landolt
Im concerned about a safety factor in the paper, A Solvent-Free Oxidation of Alcohols in an Organic Laboratory".
Landolt, R. G. J. Chem. Educ. 2004, 81, 641.
Alcohols |
Synthesis
Outrunning Nature: Directed Evolution of Superior Biocatalysts  Ryan Woodyer, Wilfred Chen, and Huimin Zhao
Although it essentially replicates the Darwinian evolutionary processes in a test tube, directed evolution can create biocatalysts with better catalytic performance than Nature's own products within weeks or months rather than eons. In this article, both the technologies and applications of directed evolution in biocatalysis are discussed.
Woodyer, Ryan; Chen, Wilfred; Zhao, Huimin. J. Chem. Educ. 2004, 81, 126.
Biotechnology |
Enzymes |
Synthesis
An Efficient Procedure for Microscale Synthesis of Semicarbazones  Sangeeta Pandita, Samta Goyal, Nadira Arif, and Sarita Passey
An efficient procedure that involves grinding together semicarbazide hydrochloride, sodium acetate, and a carbonyl compound has been developed for microscale synthesis of semicarbazones.
Pandita, Sangeeta; Goyal, Samta; Arif, Nadira; Passey, Sarita. J. Chem. Educ. 2004, 81, 108.
Microscale Lab |
Synthesis
Preparation of Two Luminescent Complexes: AlIII(8-hydroxyquinolinolato)3 and EuIII(thenoyltrifluoroacetonato)3 (1,10-phenanthroline)  Qinde Liu and Suning Wang
A simple procedure for the syntheses of two luminescent compounds, which are widely used in organic light- emitting diodes. This experiment is suitable for an undergraduate inorganic laboratory and demonstrates the role of chelating ligands in the formation of complexes and luminescence.
Liu, Qinde; Wang, Suning. J. Chem. Educ. 2003, 80, 1474.
Coordination Compounds |
Synthesis |
Photochemistry |
Materials Science
A Solvent-Free Claisen Condensation Reaction for the Organic Laboratory  John J. Esteb and Matthew B. Stockton
An experiment involving the Claisen condensation reaction for a first-year organic chemistry laboratory is presented. In this experiment, potassium tert-butoxide and ethyl phenylacetate are heated to 100 C for 30 minutes under solvent-free conditions to produce 2,4-diphenyl acetoacetate in 80% yield.
Esteb, John J.; Stockton, Matthew B. J. Chem. Educ. 2003, 80, 1446.
Synthesis |
Esters
The Art of Writing Reasonable Organic Reaction Mechanisms, 2nd Edition (Robert B. Grossman)  R. W. Holman
The emphasis is upon equipping the student with an intuitive sense of how to tackle a complex organic transformation and develop a reasonable mechanism to explain the chemistry.
Holman, R. W. J. Chem. Educ. 2003, 80, 1259.
Synthesis |
Mechanisms of Reactions
A Solvent-Free Oxidation of Alcohols in an Organic Laboratory  John J. Esteb, Michael W. Schelle, and Anne M. Wilson
Oxidation of alcohols using potassium permanganate and copper(II) sulfate pentahydrate.
Esteb, John J.; Schelle, Michael W.; Wilson, Anne M. J. Chem. Educ. 2003, 80, 907.
IR Spectroscopy |
Synthesis |
Solids
Advanced Organic Chemistry, 4th Edition. Part B: Reactions and Synthesis, (Richard J. Sundberg and Francis A. Carey)  Thomas G. Waddell
Graduate level reference text focussing on organic reactions and syntheses.
Waddell, Thomas G. J. Chem. Educ. 2003, 80, 883.
Mechanisms of Reactions |
Synthesis |
Reactions
Cyclopalladation of Phenyl-(2,4,6-trimethylbenzylidene)-amine: An Undergraduate Organometallic Laboratory Experiment  Joan Albert, Magali Cadena, and Jaume Granell
Procedure to synthesize a six-membered cyclopalladated complex by activation of an aliphatic carbon-hydrogen bond.
Albert, Joan; Cadena, Magali; Granell, Jaume. J. Chem. Educ. 2003, 80, 801.
NMR Spectroscopy |
Organometallics |
Coordination Compounds |
Synthesis
Synthesis of Zinc Iodide Revisited  Stephen DeMeo
Synthesis of zinc iodide through a reaction between barium iodide and zinc sulfate, qualitative analysis of the products, and analysis of a side reaction involved in the production of zinc iodide from its elements in an acetic acid medium.
DeMeo, Stephen. J. Chem. Educ. 2003, 80, 796.
Qualitative Analysis |
Stoichiometry |
Reactions |
Synthesis
Arts and Sciences Reunite in Nanoput: Communicating Synthesis and the Nanoscale to the Layperson  Stephanie H. Chanteau, Troy Ruths, and James M. Tour
Combining art and chemistry by producing nanoscale, monomolecular stick figures to help non-chemists appreciate organic syntheses.
Chanteau, Stephanie H.; Ruths, Troy; Tour, James M. J. Chem. Educ. 2003, 80, 395.
Nanotechnology |
Synthesis
Top Drugs: Top Synthetic Routes (Oxford Chemistry Primer No. 90) (by John Saunders)  R. Daniel Libby
Resource that explores the syntheses of a number of important drugs.
Libby, R. Daniel. J. Chem. Educ. 2003, 80, 147.
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
Chemical Recycling of Pop Bottles: The Synthesis of Dibenzyl Terephthalate from the Plastic Polyethylene Terephthalate  Craig J. Donahue, Jennifer A. Exline, and Cynthia Warner
Procedure in which students depolymerize a common plastic (PET from 2-L pop bottles) under mild conditions using nontoxic chemicals to produce monomer building blocks.
Donahue, Craig J.; Exline, Jennifer A.; Warner, Cynthia. J. Chem. Educ. 2003, 80, 79.
Industrial Chemistry |
Synthesis |
Aromatic Compounds |
Polymerization
Synthesis of 4-Methylumbellifer-7-yl-α-D-Mannopyranoside: An Introduction to Modern Glycosylation Reactions  Christophe Penverne and Vincent Ferrières
Four-step organic synthesis to introduce some concepts of glycochemistry.
Penverne, Christophe; Ferrières, Vincent. J. Chem. Educ. 2002, 79, 1353.
Carbohydrates |
Natural Products |
Synthesis
Triboluminescent Crystals from the Microwave Oven  Bruce W. Baldwin and David M. Wilhite
Procedure for producing triboluminescent crystals in a microwave oven.
Baldwin, Bruce W.; Wilhite, David M. J. Chem. Educ. 2002, 79, 1344.
Aromatic Compounds |
Crystals / Crystallography |
Synthesis |
Photochemistry
Microscale Chemistry in a Plastic Petri Dish: Preparation and Chemical Properties of Chlorine Gas  Martin M. F. Choi
Presenting some reactions of chlorine in a volume about the size of a water droplet enclosed within a petri dish.
Choi, Martin M. F. J. Chem. Educ. 2002, 79, 992.
Synthesis |
Microscale Lab
Epoxide Reactions  Thomas Bertolini
Puzzle involving epoxide reactions.
Bertolini, Thomas. J. Chem. Educ. 2002, 79, 828.
Synthesis |
Epoxides |
Ethers
Incorporation of the CrossFire Beilstein Database into the Organic Chemistry Curriculum at the Royal Danish School of Pharmacy  S. Brøgger Christensen, Henrik Franzyk, Bente Frølund, Jerzy W. Jaroszewski, Dan Stærk, and Per Vedsø
Using the online CrossFire Beilstein database in organic chemistry.
Christensen, S. Brøgger; Franzyk, Henrik; Frølund, Bente; Jaroszewski, Jerzy W.; Stærk, Dan; Vedsø, Per. J. Chem. Educ. 2002, 79, 765.
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Molecular Properties / Structure
Preparation of Aniline Derivatives: An Advanced Undergraduate Laboratory Experiment Exploring Catalytic and Stoichiometric Reaction Methodologies  Joan Colom, Antoni Llobet, Anna Pla-Quintana, and Anna Roglans
Investigating the contrasts between stoichiometric and catalytic reactions.
Colom, Joan; Llobet, Antoni; Pla-Quintana, Anna; Roglans, Anna. J. Chem. Educ. 2002, 79, 731.
Catalysis |
Synthesis |
Transition Elements |
Stoichiometry
Chiral Compounds and Green Chemistry in Undergraduate Organic Laboratories: Reduction of a Ketone by Sodium Borohydride and Baker's Yeast  Nicola Pohl, Allen Clague, and Kimberly Schwarz
Students compare biological and chemical means of introducing chirality into a molecule by investigating the reduction of a ketoester with two different reducing agents.
Pohl, Nicola; Clague, Allen; Schwarz, Kimberly. J. Chem. Educ. 2002, 79, 727.
Chirality / Optical Activity |
Oxidation / Reduction |
Synthesis |
Green Chemistry
Transition Metal Carbonyl Cluster Chemistry (by Paul J. Dyson and J. Scott McIndoe)  Linda H. Doerrer
Summary of what one ought to know as a practicing carbonyl chemist.
Doerrer, Linda H. J. Chem. Educ. 2002, 79, 677.
Synthesis |
Transition Elements |
Coordination Compounds
Oligosaccharides: Their Synthesis and Biological Roles (by Helen Osborn and Tariq Kahn)  Michael C. Shelton

Shelton, Michael C. J. Chem. Educ. 2002, 79, 562.
Carbohydrates |
Synthesis
Introduction to Synthetic Polymers, 2nd Edition (by Ian M. Campbell)  Dean Waldow

Waldow, Dean. J. Chem. Educ. 2002, 79, 561.
Synthesis
Keto-Enol Tautomers in a Carbonyl Phosphonium Salt  David E. Berry and G. W. Patenaude
Observations of keto-enol tautomers of a phosphonium ion.
Berry, David E.; Patenaude, G. W. J. Chem. Educ. 2002, 79, 498.
Synthesis |
NMR Spectroscopy |
Organometallics |
Resonance Theory
Simple Synthesis and Characterization of Several Nickel Catalytic Precursors  Yolanda Cesteros, Pilar Salagre, Francisco Medina, and Jesus E. Sueiras
Procedure for the simple synthesis and characterization of several nickel catalytic precursors.
Cesteros, Yolanda; Salagre, Pilar; Medina, Francisco; Sueiras, Jesus E. J. Chem. Educ. 2002, 79, 489.
Catalysis |
Materials Science |
Solid State Chemistry |
Synthesis
An Organic Puzzle Using Meldrum's Acid  R. David Crouch and Michael S. Holden
Organic synthesis in which the product is not easily predicted, requiring identification through an analysis of the data and consideration of possible reactions of the reagents and solvent.
Crouch, R. David; Holden, Michael S. J. Chem. Educ. 2002, 79, 477.
NMR Spectroscopy |
Synthesis |
Microscale Lab |
Esters |
Synthesis
The Michael Reaction  Thomas Poon, Bradford P. Mundy, and Thomas W. Shattuck
Biography, overview, computational analysis, and examples of the Michael reaction in organic syntheses and natural systems.
Poon, Thomas; Mundy, Bradford P.; Shattuck, Thomas W. J. Chem. Educ. 2002, 79, 264.
Computational Chemistry |
Synthesis |
Mechanisms of Reactions
Microscale Synthesis of a Diphenylisoxazoline by a 1,3-Dipolar Cycloaddition  William B. Martin, Laura J. Kateley, Dawn C. Wiser, and Catherine A. Brummond
Synthesis in which two possible pathways are possible; students use NMR to identify the product and molecular modeling to explain the preferred pathway.
Martin, William B.; Kateley, Laura J.; Wiser, Dawn C.; Brummond, Catherine A. J. Chem. Educ. 2002, 79, 225.
Microscale Lab |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Heterocycles
Use of 15N Label in Organic Synthesis and Spectroscopy. Part I: Preparation of 15N-Labeled tert-Butylamine  Erach R. Talaty, Christopher A. Boese, Sanni M. Adewale, Mohammed S. Ismail, Frank A. Provenzano, and Melissa J. Utz
Procedure for preparation of 15N-labeled tert-butylamine through the Ritter reaction followed by hydrolysis.
Talaty, Erach R.; Boese, Christopher A.; Adewale, Sanni M.; Ismail, Mohammed S.; Provenzano, Frank A.; Utz, Melissa J. J. Chem. Educ. 2002, 79, 221.
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Amines / Ammonium Compounds |
Mechanisms of Reactions
Organometallic Mediated Organic Synthesis: A Reaction Sequence for an Advanced Integrated Laboratory Course  David B. Ball and Randy Wilson
Procedure that introduces students to inorganic chemistry via organometallic mediated organic synthesis.
Ball, David B.; Wilson, Randy. J. Chem. Educ. 2002, 79, 112.
NMR Spectroscopy |
Synthesis |
Organometallics
Wittig Reaction: The Synthesis of trans-9-(2-Phenylethenyl)anthracene Revisited  Christine Jaworek and Sarah Iacobucci
Improvements on a favorable Wittig reaction synthesis.
Jaworek, Christine; Iacobucci, Sarah. J. Chem. Educ. 2002, 79, 111.
Chromatography |
Photochemistry |
Microscale Lab |
Synthesis
Synthesis of Quinolines and Their Characterization by 2-D NMR Spectroscopy  Pamela J. Seaton, R. Thomas Williamson, Abhijit Mitra, and Ali Assarpour
Synthesis of quinolines and their characterization by 2-D NMR spectroscopy.
Seaton, Pamela J.; Williamson, R. Thomas; Mitra, Abhijit; Assarpour, Ali. J. Chem. Educ. 2002, 79, 106.
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Heterocycles
Introducing Freshmen Students to the Practice of Solid-Phase Synthesis  Alpay Taralp, Can Hulusi Türkseven, Atilla Özgür Çakmak, and Ömer Çengel
Procedure to introduce freshmen to the principles and practice of solid-phase (peptide) synthesis.
Taralp, Alpay; Türkseven, Can Hulusi; Çakmak, Atilla Özgür; Çengel, Ömer. J. Chem. Educ. 2002, 79, 87.
Biotechnology |
Enzymes |
Synthesis |
Proteins / Peptides |
Undergraduate Research
Solid-Phase Organic Synthesis and Combinatorial Chemistry: A Laboratory Preparation of Oligopeptides  George A. Truran, Karelle S. Aiken, Thomas R. Fleming, Peter J. Webb, and J. Hodge Markgraf
Procedure introducing students to solid-phase organic synthesis and combinatorial chemistry.
Truran, George A.; Aiken, Karelle S.; Fleming, Thomas R.; Webb, Peter J.; Markgraf, J. Hodge. J. Chem. Educ. 2002, 79, 85.
Synthesis |
Proteins / Peptides |
Polymerization
Synthesis and Characterization of a Hyperbranched Copolymer  A. Timothy Royappa
Procedure that introduces students to hyperbranched polymers, ionic and ring-opening polymerization reactions, and the synthesis of copolymers.
Royappa, A. Timothy. J. Chem. Educ. 2002, 79, 81.
Synthesis |
Polymerization
Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives (by Henning Hopf)   Ronald M. Magid
Fundamental hydrocarbon research from the middle 50 years of the 20th century.
Magid, Ronald M. J. Chem. Educ. 2002, 79, 34.
Synthesis
Preparation of a D-Glucose-Derived Alkene. An E2 Reaction for the Undergraduate Organic Chemistry Laboratory  Peter Norris and Andrew Fluxe
Synthesis of four carbohydrate derivatives that highlight techniques such as inert atmosphere work, rotary evaporators, and flash column chromatography.
Norris, Peter; Fluxe, Andrew. J. Chem. Educ. 2001, 78, 1676.
Carbohydrates |
NMR Spectroscopy |
Synthesis |
Alkenes |
Elimination Reactions |
Chromatography
Phototropic Reaction (re J. Chem. Educ. 2000, 77, 1386-1387)  Addison Ault
Incorrect interpretation of the mechanism of a photochemical reaction.
Ault, Addison. J. Chem. Educ. 2001, 78, 1596.
Crystals / Crystallography |
Synthesis |
Photochemistry |
Mechanisms of Reactions
Phototropic Reaction (re J. Chem. Educ. 2000, 77, 1386-1387)  Paul Rademacher
Incorrect interpretation of the mechanism of a photochemical reaction.
Rademacher, Paul. J. Chem. Educ. 2001, 78, 1596.
Crystals / Crystallography |
Synthesis |
Photochemistry |
Mechanisms of Reactions
Synthesis and Self-Assembly of the "Tennis Ball" Dimer and Subsequent Encapsulation of Methane. An Advanced Organic Chemistry Laboratory Experiment  Fraser Hof, Liam C. Palmer, and Julius Rebek Jr.
Solution-phase self-assembly of the "tennis ball" dimer and encapsulation of methane.
Hof, Fraser; Palmer, Liam C.; Rebek, Julius, Jr. J. Chem. Educ. 2001, 78, 1519.
Noncovalent Interactions |
Molecular Recognition |
NMR Spectroscopy |
Synthesis
The Hydrogenation of Cyclododecene by Lithium Naphthalenide and Nickel Chloride Dihydrate  Francisco Alonso and Miguel Yus
Transformation of cyclododecene into cyclododecane in the absence of external hydrogen as an alternative to the normal method of catalytic hydrogenation.
Alonso, Francisco; Yus, Miguel. J. Chem. Educ. 2001, 78, 1517.
Synthesis |
Alkanes / Cycloalkanes |
Alkenes |
Metals
Indigo and Tyrian Purple--In Nature and in the Lab  Paul F. Schatz
Structure and brief history of the dyes Tyrian purple, indigo, and 5-5'-dibromoindigo.
Schatz, Paul F. J. Chem. Educ. 2001, 78, 1442.
Dyes / Pigments |
Synthesis |
Natural Products
Mass Spectral Fragmentation Patterns of Deuterated Butyl and Ethyl Acetates: An Easy Microscale Isotopic Labeling Experiment  Hengameh Zahedkargaran and Leverett R. Smith
Microscale experiment that illustrates the use of isotopic labeling to help confirm and interpret mass spectral fragmentation patterns.
Zahedkargaran, Hengameh; Smith, Leverett R. J. Chem. Educ. 2001, 78, 1379.
Chromatography |
Isotopes |
Mass Spectrometry |
Microscale Lab |
Synthesis |
Gas Chromatography
An Improved Preparation of a-D-(+)-Glucopyranose Pentaacetate  Paul F. Schatz
Using iodine rather than zinc chloride as a Lewis-acid catalyst in the preparation of alpha-(+)-glucopyranose pentaacetate.
Schatz, Paul F. J. Chem. Educ. 2001, 78, 1378.
NMR Spectroscopy |
Synthesis |
Laboratory Management |
Catalysis
Moving Past Markovnikov's Rule  E. Eugene Gooch
Extension of the Markovnikov Rule for addition reactions across a carbon-carbon double bond.
Gooch, E. Eugene. J. Chem. Educ. 2001, 78, 1358.
Synthesis |
Reactions |
Alkenes |
Addition Reactions |
Mechanisms of Reactions
1,5 Cyclooctadiene Complexes of Iridium: Synthesis, Characterization, and Reaction with Dihydrogen. An Experiment for an Integrated Physical/Inorganic Laboratory Course  John W. Logan and Mark Wicholas
In situ reaction of (Ir(COD)Ph3P)2]BF4 with H2 in acetone-d6 solution in a valve NMR tube.
Logan, John W.; Wicholas, Mark. J. Chem. Educ. 2001, 78, 1272.
Coordination Compounds |
Synthesis |
NMR Spectroscopy |
Organometallics
Looking beyond the endo Rule in a Diels-Alder Discovery Lab  Ronald M. Jarret, Jamie New, Rebecca Hurley, and Laura Gillooly
Procedure to introduce preference for generation of the endo product and the stereochemistry of alkene addition of the Diels-Alder reaction.
Jarret, Ronald M.; New, Jamie; Hurley, Rebecca; Gillooly, Laura. J. Chem. Educ. 2001, 78, 1262.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Alkenes
Superconductor Synthesis--An Improvement  Bradley D. Fahlman
Report on a significant improvement in the synthesis of YBa2Cu3O7-sigma(YBCO), a superconductor commonly used in undergraduate laboratories.
Fahlman, Bradley D. J. Chem. Educ. 2001, 78, 1182.
Synthesis |
Materials Science |
Solid State Chemistry |
Conductivity
Temperature Data from Biblical Narratives  J. C. Jones
Report on a significant improvement in the synthesis of YBa2Cu3O7-sigma(YBCO), a superconductor commonly used in undergraduate laboratories.
Jones, J. C. J. Chem. Educ. 2001, 78, 1182.
Synthesis |
Materials Science |
Solid State Chemistry |
Conductivity
The Biginelli Reaction  Michael S. Holden and R. David Crouch
Procedure illustrating the Biginelli reaction.
Holden, Michael S.; Crouch, R. David. J. Chem. Educ. 2001, 78, 1104.
Microscale Lab |
Synthesis |
Reactions |
Mechanisms of Reactions |
Esters |
Heterocycles
Simple Preparation and NMR Analysis of mer and fac Isomers of Tris(1,1,1-trifluoro-2,4-pentanedionato)cobalt(III). An Experiment for the Inorganic Chemistry Laboratory  Ashley W. Jensen and Brian A. O'Brien
A one-step procedure for the preparation of tris(1,1,1-trifluoro-2,4-pentanedionato)cobalt(III) from hydrated cobalt(II) carbonate and 10% hydrogen peroxide, in which tert-butyl alcohol is used as a component of the solvent.
Jensen, Ashley W.; O'Brien, Brian A. J. Chem. Educ. 2001, 78, 954.
Chromatography |
Coordination Compounds |
Synthesis |
NMR Spectroscopy |
Stereochemistry
Synthesis and Reactivity of the Metallaborane Complex [Mo(CO)4B3H8]- and the Formation of Mo(CO)4(dppe)  Craig M. Davis and Megan F. Klein
Exercise that features inert-atmosphere syntheses and multinuclear (1H, 11B, and 31P) NMR spectroscopy and is suitable for upper-level undergraduates; the skills and ideas that are taught or reinforced include a general overview of borane clusters and the isolobal analogy, handling air-sensitive solutions, and internuclear coupling in NMR spectra.
Davis, Craig M.; Klein, Megan F. J. Chem. Educ. 2001, 78, 952.
Coordination Compounds |
Metals |
Synthesis
Oxidation of Benzoin to Benzil Using Alumina-Supported Active MnO2  R. David Crouch, Michael S. Holden, and Jennifer S. Burger
Oxidation of benzoin to benzil using alumina-supported active MnO2; purification of the products using column chromatography.
Crouch, R. David; Holden, Michael S.; Burger, Jennifer S. J. Chem. Educ. 2001, 78, 951.
Chromatography |
Microscale Lab |
Synthesis |
Oxidation / Reduction
A Microscale Birch Reduction for the Advanced Organic Chemistry Laboratory  Mary Ann M. Fuhry, Christie Colosimo, and Kathleen Gianneschi
Conducting a Birch reduction in a Winston sublimator.
Fuhry, Mary Ann M.; Colosimo, Christie; Gianneschi, Kathleen. J. Chem. Educ. 2001, 78, 949.
Microscale Lab |
Synthesis |
Oxidation / Reduction |
Laboratory Equipment / Apparatus
Suzuki Cross-Coupling Reactions: Synthesis of Unsymmetrical Biaryls in the Organic Laboratory  Christopher S. Callam and Todd L. Lowary
Laboratory that exposes students to organometallic chemistry and application of the Suzuki reaction.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 947.
Aromatic Compounds |
Metals |
Synthesis |
Organometallics |
Transition Elements |
Mechanisms of Reactions
An Alternative One-Step Procedure for the Conversion of Piperonal to Piperonylnitrile  James M. DeMott Jr. and Charles J. Kelley
An alternative procedure is presented for the conversion of piperonal to piperonylonitrile; advantages of this method include shortened time, better overall yield, and improvement in safety.
DeMott, James M., Jr.; Kelley, Charles J. J. Chem. Educ. 2001, 78, 780.
Microscale Lab |
Synthesis |
Laboratory Management
Metal Complexes of Trifluoropentanedione. An Experiment for the General Chemistry Laboratory  Robert C. Sadoski, David Shipp, and Bill Durham
Investigation of the transition-metal complexes produced by the reactions of Cr(III), Mn(II), Fe(III), Co(II), Ni(II), and Cu(II) with 1,1,1-trifluoro-2,4-pentanedione; mass spectroscopy is used to determine the stoichiometry of the reaction products.
Sadoski, Robert C.; Shipp, David; Durham, Bill. J. Chem. Educ. 2001, 78, 665.
Coordination Compounds |
Synthesis |
Mass Spectrometry |
Transition Elements |
Stoichiometry
Ruthenium(II)-dppm Coordination Chemistry. An Advanced Inorganic Miniproject  Simon J. Higgins
A guided miniproject involving aspects of Ru(II)-diphosphine complex synthesis and characterization that combines teaching of new synthetic and characterization techniques with the opportunity for research work.
Higgins, Simon J. J. Chem. Educ. 2001, 78, 663.
Coordination Compounds |
Synthesis |
NMR Spectroscopy |
Undergraduate Research
Synthesis of Substituted Butenolides. An Undergraduate Organic Laboratory Experiment Utilizing Two 3-Step Preparatory Sequences  Géraldine Maheut, Liang Liao, Jean-Marie Catel, Paul-Alain Jaffrès, and Didier Villemin
The synthesis of substituted butenolide in two, 3-step sequences that illustrate five basic organic reactions (alkyne hydration, Knoevenagel condensation, lactonization, aldolization-type reaction, and hydration of nitrile); the products have pedagogical interest for IR and NMR spectroscopy (diastereotopic effect).
Maheut, Géraldine; Liao, Liang; Catel, Jean-Marie; Jaffrès, Paul-Alain; Villemin, Didier. J. Chem. Educ. 2001, 78, 654.
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Undergraduate Research |
Reactions
Controlled/Living Radical Polymerization in the Undergraduate Laboratories. 1. Using ATRP to Prepare Block and Statistical Copolymers of n-Butyl Acrylate and Styrene  Kathryn L. Beers, Brian Woodworth, and Krzysztof Matyjaszewski
A simple method of preparing well-defined (co)polymers. The method utilizes atom transfer radical polymerization (ATRP), a controlled/living radical polymerization, to prepare difunctional poly(n-butyl acrylate) with bromine end groups, which is chain-extended with styrene to yield an ABA triblock copolymer. Simultaneously, a statistical copolymer of the two monomers is prepared for comparison.
Beers, Kathryn L.; Woodworth, Brian; Matyjaszewski, Krzysztof. J. Chem. Educ. 2001, 78, 544.
Catalysis |
Materials Science |
Synthesis |
Polymerization
Small-Scale Filtration Using a Modified Plastic Syringe  Mikael Begtrup
A simple procedure is described for manual, small-scale pressure filtration performed in a modified plastic syringe.
Begtrup, Mikael. J. Chem. Educ. 2001, 78, 543.
Synthesis |
Laboratory Equipment / Apparatus |
Microscale Lab |
Separation Science
An Indexed Combinatorial Library: The Synthesis and Testing of Insect Repellents  William H. Miles, Kathy A. Gelato, Kristen M. Pompizzi, Aislinn M. Scarbinsky, Brian K. Albrecht, and Elaine R. Reynolds
An indexed combinatorial library of amides was prepared by the reaction of amines and acid chlorides; a simple test for insect repellency using fruit flies (Drosophila melanogaster) allowed the determination of the most repellent sublibraries.
Miles, William H.; Gelato, Kathy A.; Pompizzi, Kristen M.; Scarbinsky, Aislinn M.; Albrecht, Brian K.; Reynolds, Elaine R. J. Chem. Educ. 2001, 78, 540.
Drugs / Pharmaceuticals |
Synthesis |
Combinatorial Chemistry |
Applications of Chemistry |
Amines / Ammonium Compounds
Diastereoselective Synthesis of (+/-)-1,2-Diphenyl-1,2-propanediol. A Discovery-Based Grignard Reaction Suitable for a Large Organic Lab Course  James A. Ciaccio, Roxana P. Bravo, Antoinette L. Drahus, John B. Biggins, Rosalyn V. Concepcion, and David Cabrera
An experiment that probes the diastereoselectivity of the reaction between a Grignard reagent and a common, inexpensive alpha-chiral ketone; introduces students to pi-facial discrimination by having them establish the stereochemical course of kinetically controlled nucleophilic addition to a carbonyl.
Ciaccio, James A.; Bravo, Roxana P.; Drahus, Antoinette L.; Biggins, John B.; Concepcion, Rosalyn V.; Cabrera, David. J. Chem. Educ. 2001, 78, 531.
Mechanisms of Reactions |
Synthesis |
Organometallics |
Stereochemistry |
Grignard Reagents |
Aldehydes / Ketones
The Oxidation of Alkylbenzenes: Using Data Pooling in the Organic Laboratory to Illustrate Research in Organic Chemistry  James C. Adrian Jr. and Leslie A. Hull
Student groups are assigned the task of oxidizing various substituted alkylbenzenes with potassium permanganate in basic solution; by pooling the results from all groups it is possible to illustrate how a research project in chemistry can be used to answer simple questions - What happens when your individual alkylbenzene is oxidized?
Adrian, James C., Jr.; Hull, Leslie A. J. Chem. Educ. 2001, 78, 529.
Synthesis |
Chemometrics |
Oxidation / Reduction |
Mechanisms of Reactions |
Aromatic Compounds
Correction to "Drug Metabolism: The Body's Defense against Chemical Attack" (J. Chem. Educ. 2000, 77, 349-353)  
Corrections to molecular structures.
J. Chem. Educ. 2001, 78, 312.
Carbohydrates |
Drugs / Pharmaceuticals |
Enzymes |
Medicinal Chemistry |
Metabolism |
Synthesis
Correction to "Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory" (J. Chem. Educ. 2001, 78, 73-74)  
Correction to Scheme 1.
J. Chem. Educ. 2001, 78, 312.
Carbohydrates |
Medicinal Chemistry |
NMR Spectroscopy |
Synthesis
Correction to "Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory" (J. Chem. Educ. 2001, 78, 73-74)  
Correction to Scheme 1.
J. Chem. Educ. 2001, 78, 312.
Carbohydrates |
Medicinal Chemistry |
NMR Spectroscopy |
Synthesis
The Synthesis and Analysis of Copper(I) Iodide. A First-Year Laboratory Project  Lara A. Margolis, Richard W. Schaeffer, and Claude H. Yoder
This project provides a convenient preparation of a compound whose identity will not be obvious to students. The analytical procedures illustrate the fundamentals of gravimetric analysis and some basic chemical and physical characteristics of the elements. The analytical data allow students to find the identity of the product by determining its empirical formula.
Margolis, Lara A.; Schaeffer, Richard W.; Yoder, Claude H. J. Chem. Educ. 2001, 78, 235.
Synthesis |
Oxidation / Reduction |
Stoichiometry |
Gravimetric Analysis |
Qualitative Analysis |
Stoichiometry
The Dibenzalacetone Reaction Revisited  Leslie A. Hull
Groups of students are assigned target molecules of the dibenzalketone type and are given a sample procedure for the parent dibenzalacetone reaction. They are asked to design a synthesis of their target based on the model reaction and to modify the model reaction so it will work for their synthesis. They show they have synthesized the target with 1H NMR.
Hull, Leslie A. J. Chem. Educ. 2001, 78, 226.
Microscale Lab |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
Synthesis of [RuCl2(dppb)(PPh3)] and Identification of the cis- and trans-[RuCl2(dppb)(phen)] Geometrical Isomers via 31P{1H} NMR Spectroscopy. An Undergraduate Experiment for Inorganic Chemistry  Salete L. Queiroz, Márcio P. de Araujo, Alzir A. Batista, Kenneth S. MacFarlane, and Brian R. James
Demonstrates the use of 31P{1H} NMR to distinguish between cis and trans geometric isomers of coordination compounds in solution, describes the concept of spin-spin coupling for P atoms by assigning signals to equivalent and nonequivalent P atoms, and offers an introduction to synthesis and in situ NMR work requiring semirigorous, inert-atmosphere conditions.
Queiroz, Salete L.; de Araujo, Márcio P.; Batista, Alzir A.; MacFarlane, Kenneth S.; James, Brian R. J. Chem. Educ. 2001, 78, 87.
Coordination Compounds |
Synthesis |
Mechanisms of Reactions |
Transition Elements |
Diastereomers |
NMR Spectroscopy
Synthesis of a Partially Protected Azidodeoxy Sugar. A Project Suitable for the Advanced Undergraduate Organic Chemistry Laboratory  Peter Norris, Scott Freeze, and Christopher J. Gabriel
Two-step synthesis of a partially protected azidodeoxy sugar demonstrating several important concepts (alcohol activation, steric hindrance, nucleophilic substitution), offering products amenable to analysis by high field NMR, and involving techniques such as monitoring reactions by TLC, workup of reaction mixtures, and isolation by flash chromatography.
Norris, Peter; Freeze, Scott; Gabriel, Christopher J. J. Chem. Educ. 2001, 78, 75.
Carbohydrates |
Chromatography |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
Synthesis and Spectroscopic Analysis of a Cyclic Acetal: A Dehydration Performed in Aqueous Solution  David M. Collard, Adolphus G. Jones, and Robert M. Kriegel
Treatment of pentaerythritol with benzaldehyde in aqueous acid to produce the monoacetal, 5,5-bis(hydroxymethyl)-2-phenyl-1,3-dioxane. The reaction has a number of interesting features: the isolated product is the monobenzal not the dibenzal, and the reaction, a dehydration, is performed in water.
Collard, David M.; Jones, Adolphus G.; Kriegel, Robert M. J. Chem. Educ. 2001, 78, 70.
NMR Spectroscopy |
Synthesis |
Aldehydes / Ketones |
Alcohols
Determination of the Regiochemistry of Disubstituted Arenes Generated by Addition of a Carbanion to the (h6-Anisole)Cr(CO)3 Complex  Ashfaq A. Bengali, Cindy Samet, and Samantha B. Charlton
A laboratory activity that integrates fundamental concepts of organic and organometallic chemistry and then employs standard instrumental techniques (GC) and molecular modeling to justify the results.
Bengali, Ashfaq A.; Samet, Cindy; Charlton, Samantha B. J. Chem. Educ. 2001, 78, 68.
Aromatic Compounds |
Synthesis |
Organometallics |
Gas Chromatography |
Molecular Modeling
Design of Experiments (about J. Chem. Educ. 1999, 76, 1560-1561)  David M. Birney

Birney, David M. J. Chem. Educ. 2000, 77, 1557.
Biotechnology |
Natural Products |
Synthesis
Design of Experiments (about J. Chem. Educ. 1999, 76, 1560-1561)  Benjamin J. Luberoff

Luberoff, Benjamin J. J. Chem. Educ. 2000, 77, 1557.
Biotechnology |
Natural Products |
Synthesis
Standardizing Iodine (about J. Chem. Educ. 1999, 76, 1421-1422)  Stephen J. Hawkes

Hawkes, Stephen J. J. Chem. Educ. 2000, 77, 1557.
Biotechnology |
Natural Products |
Synthesis |
Quantitative Analysis
A Phthalocyanine Synthesis Group Project for General Chemistry  Darren K. MacFarland, Christopher M. Hardin, and Michael J. Lowe
A group experiment synthesizing phthalocyanine dyes in one step from commercially available starting materials is described. The importance of a metal template is explored. The experiment is suitable for a second-semester general chemistry course.
MacFarland, Darren K.; Hardin, Christopher M.; Lowe, Michael J. J. Chem. Educ. 2000, 77, 1484.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
Visible Aromatic Electronic Effects Using a Series of Substituted Copper Phthalocyanines  Darren K. MacFarland, Solomon Lieb, and Jessica Oswald
Phthalocyanines provide an opportunity to directly observe electronic effects in an aromatic system through color changes that are dependent on the nature of peripheral substituents. Simple, reliable syntheses of electron-poor and electron-rich phthalocyanines are reported, along with corresponding UV-visible spectra.
MacFarland, Darren K.; Lieb, Solomon; Oswald, Jessica. J. Chem. Educ. 2000, 77, 1482.
Aromatic Compounds |
Synthesis |
Organometallics |
UV-Vis Spectroscopy |
Aromatic Compounds
A Short, One-Pot Synthesis of Bupropion (Zyban®, Wellbutrin®)  Daniel M. Perrine, Jason T. Ross, Stephen J. Nervi, and Richard H. Zimmerman
A one-pot synthesis of ()-2-(t-butylamino)-3'-chloropropiophenone (bupropion) as its hydrochloride salt (Zyban, Wellbutrin), an important antidepressant drug used in the treatment of nicotine addiction, is described. The procedure is suitable for students in their first year of organic chemistry.
Perrine, Daniel M.; Ross, Jason T.; Nervi, Stephen J.; Zimmerman, Richard H. J. Chem. Educ. 2000, 77, 1479.
Drugs / Pharmaceuticals |
Industrial Chemistry |
Medicinal Chemistry |
Synthesis |
Applications of Chemistry
Cyclization of the Monoterpene Citronellal to Isopulegol: A Biomimetic Natural Product Synthesis  Bruce L. Jensen, Ahmed Malkawi, and Vanessa McGowan
The experiment reported here mimics the reaction found in the biosynthetic pathway leading to another well-known natural product, menthol. The starting material and final product display easily interpreted infrared and proton-NMR spectra.
Jensen, Bruce L.; Malkawi, Ahmed; McGowan, Vanessa. J. Chem. Educ. 2000, 77, 1474.
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
Synthesis
Cornell College Students Achieve the Highly Improbable  Addison Ault
On Tuesday, March 14, 2000, at Cornell College, Mount Vernon, Iowa, two students who prepared the photochromic compound 2-(2,4-dinitrobenzyl)pyridine obtained their product as a single crystal, one weighing 864 mg and the other 891 mg. As far as we know, this has happened only once before, also at Cornell College in Iowa.
Ault, Addison. J. Chem. Educ. 2000, 77, 1386.
Crystals / Crystallography |
Synthesis |
Photochemistry
Bromination, Elimination, and Polymerization: A 3-Step Sequence for the Preparation of Polystyrene from Ethylbenzene  Elizabeth M. Sanford and Heather L. Hermann
An organic chemistry lab that introduces students to polymer chemistry is presented. Students complete a radical bromination of ethylbenzene, which is followed by elimination to give styrene. A radical polymerization is then completed to produce polystyrene.
Sanford, Elizabeth M.; Hermann, Heather L. J. Chem. Educ. 2000, 77, 1343.
Free Radicals |
Synthesis |
Polymerization
Early Exposure of Undergraduates to the Chemistry Research Environment: A New Model for Research Universities  Harriet A. Lindsay and Matthias C. McIntosh
29 student volunteers from second-semester organic chemistry lecture courses participated in a one-afternoon research experience. Each student performed one reaction directed toward the total synthesis of the anticancer natural product eleutherobin. The details of the student involvement in the project, progress of the student research efforts, teaching opportunities derived from the research, and some observations regarding student participation are described.
Lindsay, Harriet A.; McIntosh, Matthias C. J. Chem. Educ. 2000, 77, 1174.
Natural Products |
Synthesis |
Undergraduate Research
Trisethylenediaminecobalt(III) Chloride Sulfate as a Subject Material for Widely Different Chemistry Lab Courses  Yoshiki Moriguchi
A new unified lab curriculum, expanded to include an organic chemistry or stereochemistry lab course using rac-tris(ethylenediamine)cobalt(III)chloridesulfate (rac-[Co(en)3]ClSO4).
Moriguchi, Yoshiki. J. Chem. Educ. 2000, 77, 1045.
Coordination Compounds |
Synthesis |
Quantitative Analysis |
Enantiomers
The Synthesis and Analysis of Ammine Complexes of Copper and Silver Sulfate: An Undergraduate Laboratory Project  Steven S. Clareen, Shireen R. Marshall, Kristin E. Price, Margaret B. Royall, Claude H. Yoder, and Richard W. Schaeffer
An undergraduate chemistry laboratory project involving the synthesis of [Ag(NH3)2]2SO4 and Cu(NH3)4SO4 from the simple sulfate salts is described. Characterization of the stoichiometry of the complexes is accomplished by gravimetric and volumetric analysis.
Clareen, Steven S.; Marshall, Shireen R.; Price, Kristin E.; Royall, Margaret B.; Yoder, Claude H.; Schaeffer, Richard W. J. Chem. Educ. 2000, 77, 904.
Metals |
Coordination Compounds |
Synthesis |
Stoichiometry |
Gravimetric Analysis |
Titration / Volumetric Analysis
A Practical Procedure for the Solid-Phase Synthesis of Azo Compounds in the Undergraduate Organic Laboratory  Cailan Wang, Yulu Wang, Xiaoyang Wang, Xiaoxia Wang, and Hong Wang
A new solid-phase reaction method used to synthesize a new type of azo compound is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the middle weeks of a course when azo compounds or synthesis methods have been discussed in the lecture.
Wang, Cailan; Wang, Yulu; Wang, Xiaoyang; Wang, Xiaoxia; Wang, Hong. J. Chem. Educ. 2000, 77, 903.
Synthesis |
Undergraduate Research |
Aromatic Compounds
Elucidation of Molecular Structure Using NMR Long-Range Coupling: Determination of the Single Isomer Formed in a Regiospecific Reaction  Samuel Delagrange and Françoise Nepveu
The experiment presented in this article introduces students to the main concepts of two essential NMR techniques for investigating molecular structure. Heteronuclear multiple bond connectivity (HMBC) and proton-coupled 13C NMR are used to determine which isomer, from a possible two, is formed by a regiospecific reaction. The demonstration, based on long-range coupling between quaternary carbons and protons on neighboring carbons, is presented step by step.
Delagrange, Samuel; Nepveu, Françoise. J. Chem. Educ. 2000, 77, 895.
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
Carboxylic Acids |
Reactions |
Diastereomers
Microscale Synthesis of Hexaamminechromium(III) Nitrate Using Liquid Ammonia Generated in the Laboratory  Edward Maslowsky Jr.
The previously published synthesis of hexaamminechromium(III) nitrate using liquid ammonia as the solvent is simplified by performing this experiment on a microscale level and generating the small amount of ammonia needed directly in the laboratory at the time of the experiment. The ammonia is generated by heating concentrated ammonium hydroxide and condensing the ammonia vapors into the reaction vessel.
Maslowsky, Edward, Jr. J. Chem. Educ. 2000, 77, 760.
Coordination Compounds |
Synthesis |
Microscale Lab |
Solutions / Solvents
The Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments  Chriss E. McDonald

McDonald, Chriss E. J. Chem. Educ. 2000, 77, 750.
Oxidation / Reduction |
Alcohols |
Esters |
Synthesis |
Mechanisms of Reactions
Organic Reactions in Aqueous Media (by Chao-Jun Li and Tak-Hang Chan)  reviewed Alan M. Rosan
Selective review of the burgeoning literature on organic reactions conducted in water or in aqueous media as a reaction cosolvent.
Rosan, Alan M. J. Chem. Educ. 2000, 77, 707.
Aqueous Solution Chemistry |
Reactions |
Synthesis |
Mechanisms of Reactions
Epoxide Chemistry: Guided Inquiry Experiment Emphasizing Structure Determination and Mechanism  H. G. Krishnamurty, Niveta Jain, and Kiran Samby
An operationally simple three-step synthesis of an a-hydroxy acid based on epoxide chemistry. The focus of the experiment is on the preparation of the chalcone epoxide and its reaction with hot alcoholic alkali. The experiment leads to an unpredicted reaction product.
Krishnamurty, H. G.; Jain, Niveta; Samby, Kiran. J. Chem. Educ. 2000, 77, 511.
Epoxides |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis
Transition Metals in the Synthesis of Complex Organic Molecules, 2nd Edition (by L. S. Hegedus)  reviewed by Peter Wipf
This book is an update of the popular 1994 edition of Hegedus' organometallic digest for synthetic organic chemists. Literature is now covered through mid-1999.
Wipf, Peter. J. Chem. Educ. 2000, 77, 447.
Synthesis |
Metals |
Transition Elements |
Organometallics
Dediazoniations in Water: An Integrated Physical Organic Chemistry Experiment  Ugo Costas-Costas, Román Pazo-LLorente, Elisa González-Romero, and Carlos Bravo-Díaz
An integrated physical organic experiment that includes synthesis and isolation of an arenediazonium salt in the solid state and a kinetic study of its stability in water by employing both spectrophotometric and potentiometric measurements. Spectrophotometric kinetic data can be obtained by following the decrease in absorbance due to diazonium ion disappearance.
Costas-Costas, Ugo; Pazo-LLorente, Román; González-Romero, Elisa; Bravo-Díaz, Carlos. J. Chem. Educ. 2000, 77, 384.
Kinetics |
Synthesis |
Mechanisms of Reactions |
Synthesis
Isolation of Curcumin from Turmeric  Andrew M. Anderson, Matthew S. Mitchell, and Ram S. Mohan
The active ingredient in turmeric is curcumin, which is approximately 2% by weight of the root of turmeric. We have developed two simple procedures for isolation of curcumin from turmeric, making this a new and interesting natural product isolation experiment.
Anderson, Andrew M.; Mitchell, Matthew S.; Mohan, Ram S. J. Chem. Educ. 2000, 77, 359.
Chromatography |
Medicinal Chemistry |
Natural Products |
Synthesis |
Separation Science |
Aromatic Compounds
Synthesis of the Sweetener Dulcin from the Analgesic Tylenol  Brian D. Williams, Birute Williams, and Louise Rodino
A sequence suitable for the synthesis of the sweetener dulcin from the analgesic acetaminophen. The analgesic phenacetin is isolated during the synthesis as an intermediate and consequently the experiment can be adopted as a multistep synthesis or as either of two single-period transformations.
Williams, Brian D.; Williams, Birute; Rodino, Louise. J. Chem. Educ. 2000, 77, 357.
Synthesis |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Aromatic Compounds
Experiments with Aspirin  Londa L. Borer and Edward Barry
Experiments include (i) synthesis, purification, and characterization of aspirin by mp and TLC, (ii) percentage composition of a commercial aspirin tablet by titration, (iii) kinetics of the hydrolysis of aspirin to salicylic acid under various conditions, (iv) synthesis and characterization of copper(II) aspirinate and copper(II) salicylate, and (v) reaction of copper(II) aspirinate in aqueous solution.
Borer, Londa L.; Barry, Edward. J. Chem. Educ. 2000, 77, 354.
Synthesis |
Kinetics |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Aromatic Compounds
Drug Metabolism: The Body's Defense against Chemical Attack  Andrew V. Stachulski and Martin S. Lennard
It is misleading to think of drug metabolism as purely a detoxifying process. Drug metabolites can also possess significant pharmacological activity, and in some cases, serious toxicity. Case studies of the metabolism of the commonly used drugs paracetamol, terfenadine, and morphine are presented to illustrate these effects.
Stachulski, Andrew V.; Lennard, Martin S. J. Chem. Educ. 2000, 77, 349.
Metabolism |
Enzymes |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Carbohydrates |
Synthesis
Organic Synthesis: The Science behind the Art (by W. A. Smit, A. F. Bochkov, and R. Caple)   reviewed by Arthur R. Murdoch
In this book, the authors raise the question "Why do Organic Synthesis?" Now with the power of instrumentation at the chemist's disposal, total synthesis is no longer necessary for structure proof. So where does the future of organic synthesis lie?
Murdoch, Arthur R. J. Chem. Educ. 2000, 77, 314.
Synthesis
A Simple Secondary Amine Synthesis: Reductive Amination Using Sodium Triacetoxyborohydride  Merle W. Carlson, James T. Ciszewski, Micah M. Bhatti, Wesley F. Swanson, and Anne M. Wilson
A reductive amination experiment for a second-semester organic chemistry class. It utilizes an imine intermediate and sodium triacetoxyborohydride, a mild reducing agent. The progress of the reaction is followed by TLC as the starting materials (the aldehyde and primary amine), the imine intermediate, and the secondary amine product are visible under ultraviolet light.
Carlson, Merle W.; Ciszewski, James T.; Bhatti, Micah M.; Swanson, Wesley F.; Wilson, Anne M. J. Chem. Educ. 2000, 77, 270.
Synthesis |
Chromatography |
Amines / Ammonium Compounds
Reaction of Morpholine with t-Butyl Acetoacetate: A Study in Kinetic vs Thermodynamic Control, Product Identification, and Molecular Modeling  A. Gilbert Cook and Pamela K. Kreeger
The reaction of morpholine with t-butyl acetoacetate in a one-to-one molar ratio will produce the corresponding enaminoester under kinetic control conditions and the ketoamide under thermodynamic control conditions.
Cook, A. Gilbert; Kreeger, Pamela K. J. Chem. Educ. 2000, 77, 90.
NMR Spectroscopy |
Mass Spectrometry |
Computational Chemistry |
Synthesis |
Molecular Modeling
Preparation of nido-Carborane Derivatives: Variation of the 31P{1H} NMR Pattern by Changing the Coordinating Ligand. A Microscale Laboratory   O. Crespo, M. Concepción Gimeno, and Antonio Laguna
An easy synthesis that illustrates how a slight change of the ligands in a complex can determinate the pattern in the NMR spectrum. We have chosen two o-carborane derivatives because of the growing interest in the applications of such complexes.
Crespo, Olga; Gimeno, M. Concepcin; Laguna, Antonio. J. Chem. Educ. 2000, 77, 86.
Microscale Lab |
NMR Spectroscopy |
Synthesis
The Hofmann Rearrangement Using Household Bleach: Synthesis of 3-Nitroaniline  Keith A. Monk and Ram S. Mohan
A simple experiment that involves the Hofmann rearrangement of 3-nitrobenzamide to give 3-nitroaniline using household bleach. The synthesis of 3-nitrobenzamide by nitration of benzamide and the subsequent Hofmann rearrangement can be carried out in two-and-a-half hours, making this a new and simple two-step reaction sequence for the organic laboratory.
Monk, Keith A.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 1717.
NMR Spectroscopy |
Synthesis
Synthesis of Derivatives of (1R)-(-)- and (1S)-(+)-10-Camphorsulfonic Acid  Steven C. Cermak and David F. Wiemer
The preparation of optically active (camphorsulfonyl)oxaziridines from commercially available (1R)-(-) and/or (1S)-(+)10-camphorsulfonic acid provides a clear demonstration of the lack of relationship between absolute configuration and optical rotation. The parent sulfonic acid can be converted to the corresponding acid chloride and then to the sulfonamide, sulfonylimine, and finally to an oxaziridine in a series of practical organic laboratory experiments.
Cermak, Steven C.; Wiemer, David F. J. Chem. Educ. 1999, 76, 1715.
Stereochemistry |
Synthesis |
Aromatic Compounds |
Ethers |
Alcohols |
Aldehydes / Ketones |
Acids / Bases
A Simple and Efficient Ozone Generator  Debra J. Sponholtz, Michael A. Walters, Jimmy Tung, and Joseph J. BelBruno
We report on the construction of an inexpensive, efficient, and compact ozonolysis apparatus, suitable for use in oxidation chemistry, which is a convenient alternative to the more expensive generators currently on the market. The details, operating parameters, and application of the ozone generator to the oxidation of methylallyl oxazolidione are also presented.
Sponholtz, Debra J.; Walters, Michael A.; Tung, Jimmy; BelBruno, Joseph J. J. Chem. Educ. 1999, 76, 1712.
Laboratory Equipment / Apparatus |
Reactive Intermediates |
Synthesis |
Oxidation / Reduction
Microscale Transformations of Some Lead Compounds. A Cycle for Lead Minimizing the Production of Wastes  Francisco J. Arnáiz and María R. Pedrosa
This set of basic experiments emphasizes that toxic products can be conveniently studied by using a combination of microscale techniques and simple schemes to recycle wastes. Here we propose a basic cycle for lead involving the consecutive transformation of lead(II) acetate to lead(II) formate, lead powder, and lead(II) oxide, with special emphasis on minimizing the production of wastes.
Arniz, Francisco J.; Pedrosa, Mara R. J. Chem. Educ. 1999, 76, 1687.
Synthesis |
Microscale Lab
Parallel Combinatorial Esterification: A Simple Experiment for Use in the Second-Semester Organic Chemistry Laboratory  David M. Birney and Stephen D. Starnes
This simple experiment utilizes the Fischer esterification, a common reaction in second-semester organic laboratories, to demonstrate the fundamentals of combinatorial methods. These include simultaneous synthesis of numerous compounds, a selective assay for a desired activity, and an algorithm for identifying the active structure. Using a parallel synthesis combinatorial method, each student in a lab section prepares a different ester.
Birney, David M.; Starnes, Stephen D. J. Chem. Educ. 1999, 76, 1560.
Synthesis |
Natural Products |
Biotechnology |
Descriptive Chemistry |
Esters |
Combinatorial Chemistry
A Novel Target Synthesis Laboratory for Students  C. Mark Smales and David R. K. Harding
A third-year specialist course in drug design and delivery focused on a single laboratory goal for all students. A tetrapeptide, destined as the signal component of a drug delivery system, was chosen for this target synthesis. The practical, real-life aspect of the course, and the target synthesis in particular, was a major component of the appeal to the students.
Smales, C. Mark; Harding, David R. K. J. Chem. Educ. 1999, 76, 1558.
Drugs / Pharmaceuticals |
Synthesis |
Proteins / Peptides |
Medicinal Chemistry
The Preparation of Lidocaine  Thomas J. Reilly
The widely used local anesthetic Lidocaine is synthesized in two steps from 2,6-dimethylaniline. In the first step, the amine is acylated with chloroacetyl chloride. In the second step, the amide is subjected to nucleophilic substitution by diethylamine to give the final product.
Reilly, Thomas J. J. Chem. Educ. 1999, 76, 1557.
Synthesis |
Medicinal Chemistry
Reticulation Study and Molding of Unsaturated Polyester Composites  S. Bistac
This paper describes a laboratory experiment involving polyester composites, and especially sheet molding compounds (SMC), to investigate several aspects of composite science. The SMC contain an unsaturated polyester resin (blended with styrene monomer), fillers (calcium carbonate), and glass-fiber reinforcement. The mix also contains a peroxide catalyst and other additives.
Bistac, Sophie. J. Chem. Educ. 1999, 76, 1533.
Materials Science |
Synthesis
"New" Compounds from Old Plastics: Recycling PET Plastics via Depolymerization. An Activity for the Undergraduate Organic Lab  Don Kaufman, Geoff Wright, Ryan Kroemer, and Josh Engel
This paper describes work done to develop a meaningful undergraduate organic lab activity that illustrates chemistry of the real world while utilizing reactions typically included in the organic lecture and lab. We show how a common plastic can be converted into several compounds using ester hydrolysis and SN2 reactions.
Kaufman, Don; Wright, Geoff; Kroemer, Ryan; Engel, Josh. J. Chem. Educ. 1999, 76, 1525.
Consumer Chemistry |
Synthesis |
Esters |
Nucleophilic Substitution
The Preparation of a UV-Light-Absorbing Polymer: A Project-Oriented Laboratory Experiment for the Introductory Organic Chemistry Curriculum  Thomas Poon, Jean P. McIntyre, Andrea Dorigo, Drew J. Davis, Matthew A. Davis, Crystal F. Eller, Leah R. Eller, Heather K. Izumi, Kenya M. Jones, Kurt H. Kelley, William Massello, Megan L. Melamed, Cynthia M. Norris, Jeffrey A. Oelrich, Thomas A. Pluim, Sarah E. Poplawski, Jason M. St. Clair, Matthew P. Stokes, Wells C. Wheeler, and Erin E. Wilkes
A laboratory experiment is described that combines organic synthesis, spectroscopy, and polymer chemistry and is suitable for the sophomore organic chemistry curriculum. In this three-week sequence, students synthesize and characterize the UV-absorber 2-(2',4'-dimethylbenzoyl)benzoic acid and incorporate it into films of polymethylmethacrylate.
Poon, Thomas; McIntyre, Jean P.; Dorigo, Andrea; Davis, Drew J.; Davis, Matthew A.; Eller, Crystal F.; Eller, Leah R.; Izumi, Heather K.; Jones, Kenya M.; Kelley, Kurt H.; Massello, William; Melamed, Megan L.; Norris, Cynthia M.; Oelrich, Jeffrey A.; Pluim, Thomas A.; Poplawski, Sarah E.; St. Clair, Jason M.; Stokes, Matthew P.; Wheeler, Wells C.; Wilkes, Erin E. J. Chem. Educ. 1999, 76, 1523.
Synthesis |
UV-Vis Spectroscopy |
NMR Spectroscopy |
IR Spectroscopy |
Free Radicals
Macroscale and Microscale Organic Experiments, 3rd Edition (by Kenneth L. Williamson)  reviewed by James Keeffe
In this new edition, (optional) molecular mechanics calculations remain the workhorse method. These are now used in conjunction with 20 experiments, and are supplemented in some cases by suggested semiempirical computations.
Keeffe, James. J. Chem. Educ. 1999, 76, 1492.
Synthesis |
Microscale Lab |
Computational Chemistry
Metallocenes (by Nicholas J. Long)  reviewed by Daniel Rabinovich
Survey of metallocene chemistry all across the periodic table, written in a textbook format and aimed at advanced undergraduate and graduate students and researchers in the field.
Rabinovich, Daniel. J. Chem. Educ. 1999, 76, 1488.
Synthesis
Author's Reply to Micropreparation of [RuH2(PPh3)4]  Linn, Donald E.
Responses to questions regarding the synthesis of [RuH2(PPh3)4].
Linn, Donald E. J. Chem. Educ. 1999, 76, 1485.
NMR Spectroscopy |
Organometallics |
Synthesis |
Microscale Lab |
Mechanisms of Reactions
Micropreparation of [RuH2(PPh3)4]  Arnaiz, Francisco J.
Questions regarding the synthesis of [RuH2(PPh3)4].
Arnaiz, Francisco J. J. Chem. Educ. 1999, 76, 1484.
NMR Spectroscopy |
Organometallics |
Synthesis |
Microscale Lab |
Mechanisms of Reactions
trans-Cyclohexane-1,2-diamine  Treptow, Richard S.
First successful resolution of the diamine.
Treptow, Richard S. J. Chem. Educ. 1999, 76, 1484.
Chromatography |
Separation Science |
Synthesis |
Stereochemistry
Grignard Reactions in "Wet" Ether  David H. Smith
A small laboratory ultrasonic bath can be used to initiate the Grignard reaction of alkyl or aryl bromides in regular laboratory-quality, undried, diethyl ether and in simple undried test tubes.
Smith, David H. J. Chem. Educ. 1999, 76, 1427.
Synthesis |
Microscale Lab |
Grignard Reagents |
Ethers
Imidazole and Benzimidazole Synthesis (M. Ross Grimmett)  Paul G. Rasmussen
A useful reference for possible student experiments, starting materials for projects, and general information about heterocyclic ring construction.
Rasmussen, Paul G. J. Chem. Educ. 1999, 76, 1345.
Synthesis |
Heterocycles
Copper Content in Synthetic Copper Carbonate  Sheeran, D.
Thanks for correction.
Sheeran, D. J. Chem. Educ. 1999, 76, 1339.
Synthesis
Copper Content in Synthetic Copper Carbonate  Gamsjager, H.; Preis, W.
Analysis of the Cu+2 - H2O - CO2 system.
Gamsjager, H.; Preis, W. J. Chem. Educ. 1999, 76, 1339.
Synthesis
Letters  
Analysis of the Cu+2 - H2O - CO2 system.
J. Chem. Educ. 1999, 76, 1339.
Synthesis
Organic Chemistry Course Development in a Forensic Science Program: Use of FT-NMR  Ronald Callahan, Lawrence Kobilinsky, and Robert Rothchild
The acquisition of a modern, multinuclear, medium-field (7 tesla) FT-NMR, with partial support from NSF-ILI, has made possible the introduction of a major special project for second-semester organic chemistry laboratory, within a forensic science program.
Callahan, Ronald; Kobilinsky, Lawrence; Rothchild, Robert. J. Chem. Educ. 1999, 76, 1332.
Forensic Chemistry |
NMR Spectroscopy |
Synthesis |
Microscale Lab |
Molecular Modeling |
Stereochemistry
Photochemistry without Light: Oxidation of Rubrene in a Microemulsion with a Chemical Source of Singlet Molecular Oxygen (1O2, 1Dg)  Véronique Nardello, Marie-Josée Marti, Christel Pierlot, and Jean-Marie Aubry*
Illustrates the main features of excited oxygen in the singlet state: (i) its high oxidizing power and its selectivity towards unsaturated organic compounds, (ii) its low excitation energy which allows its access by various chemical processes and (iii) its long lifetime compared to the other usual excited molecules.
Nardello, Vronique; Marti, Marie-Jose; Pierlot, Christel; Aubry, Jean-Marie. J. Chem. Educ. 1999, 76, 1285.
Colloids |
Photochemistry |
Synthesis
Microscale Synthesis of Tributyl Arsenite  Francisco J. Arnáiz and Mariano J. Miranda
Arsenic trichloride is a moisture-sensitive product for which the recently reported synthesis - direct reaction of arsenic(III) oxide with excess thionyl chloride - is not as simple as it appears, because the excess thionyl chloride is difficult to remove. Here we describe a simple synthesis for tributyl arsenite that makes use of the reaction of arsenic(III) oxide with butanol.
Arniz, Francisco J.; Miranda, Mariano J. J. Chem. Educ. 1999, 76, 1251.
Synthesis |
Microscale Lab
Chemistry of Natural alpha-Amino Acids: A Surprising "One-Pot Four-Step" Conversion of Polyfunctional Enones into Cyclic Imines  Sonia Amigoni, Christophe Penverne, Caroline Nugier-Chauvin, and Yves Le Floch
This project is aimed at introducing graduate students to multistep organic synthesis. The elaboration of the proposed retrosynthetic scheme involved the use of natural a-amino acids as starting materials. The synthesis of the target polyfunctional enones allowed students to understand the importance of protective groups.
Amigoni, Sonia; Penverne, Christophe; Nugier-Chauvin, Caroline; Le Floch, Yves. J. Chem. Educ. 1999, 76, 1247.
Natural Products |
Amino Acids |
Synthesis
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds: From Cyclopropanes to Ylides (by Michael P. Doyle, M. Anthony McKervey, and Tao Ye)  David Goldsmith
Review of the role diazo compounds play in synthetic chemistry.
Goldsmith, David. J. Chem. Educ. 1999, 76, 1191.
Synthesis |
Catalysis
A Research-Based Sophomore Organic Chemistry Laboratory  D. Scott Davis, Robert J. Hargrove, and Jeffrey D. Hugdahl
The incorporation of a research component into a sophomore organic chemistry laboratory sequence is described. The students prepare a research proposal, perform the planned two-step synthesis, and present their research as a poster at a departmental "research conference".
Davis, D. Scott; Hargrove, Robert J.; Hugdahl, Jeffrey D. J. Chem. Educ. 1999, 76, 1127.
Synthesis |
Undergraduate Research
The Discovery-Oriented Approach to Organic Chemistry 2. Selectivity in Alcohol Oxidation: An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Steven R. Shadwick and Ram S. Mohan
A simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine.
Shadwick, Steven R.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 1121.
NMR Spectroscopy |
Alcohols |
Oxidation / Reduction |
Synthesis
A Facile Oxidation of Alcohols Using Pyridinium Chlorochromate/Silica Gel  Frederick A. Luzzio, Richard W. Fitch, William J. Moore, and Kelli J. Mudd
An efficient and convenient adaptation of the pyridinium chlorochromate (PCC) oxidation for an organic chemistry student exercise is based on the employment of reagent-grade silica gel, which simplifies workup and purification of the product.
Luzzio, Frederick A.; Fitch, Richard W.; Moore, William J.; Mudd, Kelli J. J. Chem. Educ. 1999, 76, 974.
Drugs / Pharmaceuticals |
Synthesis |
Natural Products |
Alcohols |
Oxidation / Reduction
A Puzzling Alcohol Dehydration Reaction Solved by GC–MS Analysis  Michael W. Pelter and Rebecca M. Macudzinski
The reaction of 2-methyl-2-propanol with ~50% sulfuric acid at 100 C yields isobutylene, which reacts further by a "puzzling" reaction. By coupling the GC/MS analysis of the product mixture with their knowledge of the mechanism of alcohol dehydration and alkene reactivity, students are able to identify the major products of this reaction.
Pelter, Michael W.; Macudzinski, Rebecca M. J. Chem. Educ. 1999, 76, 826.
Synthesis |
Microscale Lab |
Mass Spectrometry |
Gas Chromatography |
Alcohols |
Alkenes
Synthesis of a 7-Oxanorbornene Monomer: A Two-Step Sequence Preparation for the Organic Laboratory  Marcia B. France, Lisa T. Alty, and T. Markley Earl
The Diels-Alder reaction and solvolysis of an anhydride accompanied by Fischer esterification. Both of these steps produce crystals in a dramatic manner that catches the students' attention. This sequence can stand on its own as part of an organic laboratory, or the product can be utilized as a monomer for ring-opening metathesis polymerization (ROMP) studies.
France, Marcia B.; Alty, Lisa T.; Earl, T. Markley. J. Chem. Educ. 1999, 76, 659.
Synthesis |
NMR Spectroscopy
Sharpless Asymmetric Dihydroxylation: Effect of Alkene Structure on Rates and Selectivity  Alan C. Spivey, R. Hanson, N. Scorah, and S. J. Thorpe
Each student is assigned an alkene and performs three dihydroxylation reactions: one racemic and two enantioselective variants. The products are characterized by 1H NMR, IR, MS, [a]D20, and chiral chromatography (HPLC or GC). Comparison by the students of their results with those reported in the literature, particularly the extensive work of Sharpless, allows an exploration of the validity of Sharpless's mnemonic for predicting the stereochemical outcome of these reactions.
Spivey, Alan C.; Hanson, R.; Scorah, N.; Thorpe, S. J. J. Chem. Educ. 1999, 76, 655.
Synthesis |
Catalysis |
Stereochemistry |
Organometallics |
Molecular Properties / Structure
Employing NMR Spectroscopy To Evaluate Transmission of Electronic Effects in 4-Substituted Chalcones  Nanette Wachter-Jurcsak and Hossein Zamani
Described is an organic synthesis experiment that demonstrates the electronic transmission by substituents. The effect of substitution at the para-position of the styryl ring of 1,3-diphenyl-2-propenones (chalcones) by typical electron-donating or -accepting groups can be observed by proton and carbon-13 NMR spectroscopy.
Wachter-Jurcsak, Nanette; Zamani, Hossein. J. Chem. Educ. 1999, 76, 653.
NMR Spectroscopy |
Synthesis
Organic Chemistry (by Joseph M. Hornback)  R. Daniel Libby
This text uses reaction mechanisms as the organizing principle, introduces structure where it is necessary to support the reactions to be studied, and considers synthesis after the mechanisms of appropriate reactions have been discussed.
Libby, R. Daniel. J. Chem. Educ. 1999, 76, 611.
Mechanisms of Reactions |
Synthesis |
Molecular Properties / Structure
Correction to The Art and Science of Organic and Natural Products Synthesis  K. C. Nicolaou
Corrections to Figure 45.
Nicolaou, K. C. J. Chem. Educ. 1999, 76, 609.
Medicinal Chemistry |
Natural Products |
Synthesis
The Discovery-Oriented Approach to Organic Chemistry. 1. Nitration of Unknown Organic Compounds. An Exercise in 1H NMR and 13C NMR Spectrosopy for Sophomore Organic Laboratories  Sonia R. McElveen, Kostas Gavardinas, Jean A. Stamberger, and Ram S. Mohan
Two simple nitration experiments that present the student with a puzzle and are a good exercise in 1H NMR and 13C NMR spectroscopy. The experiment involves nitration of unknown organic compounds and product analysis by 1H NMR and 13C NMR spectroscopy, which enables the student to determine the identity of the unknown.
McElveen, Sonia R.; Gavardinas, Kostas; Stamberger, Jean A.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 535.
NMR Spectroscopy |
Synthesis |
Reactions
A Safe Simple Halogenation Experiment  Hilton M. Weiss and Lara Ganz
This experiment is designed to be a safe and experimentally simple procedure appropriate to the early weeks of a course when halogenation is the only reaction which has been discussed in the lecture. It can also provide some early experience with simple interpretation of NMR spectra.
Weiss, Hilton M.; Ganz, Lara. J. Chem. Educ. 1999, 76, 534.
Synthesis |
Free Radicals |
Reactions |
NMR Spectroscopy
Emil Votocek (1872-1950): A Tribute to the Chemist-Composer-Lexicographer  George B. Kauffman*, Frantisek Jursík**, and Ian D. Rae***
Although primarily known for his research on organic, analytical, inorganic, and plant chemistry, this polyglot scholar and lexicographer was also a composer who wrote nearly 60 musical compositions during the relatively short period of 15 years.
Kauffman, George B.; Jursík, Frantisek; Rae, Ian D. J. Chem. Educ. 1999, 76, 511.
Carbohydrates |
Dyes / Pigments |
Synthesis
Synthesis of Molybdenum-Molybdenum Quadruple Bonds: A Multistep Advanced Synthesis Laboratory Experiment  Laura E. Pence*, Amy M. Weisgerber, and Florence A. Maounis
An advanced synthetic inorganic experiment is described in which students prepare Mo2(O2CCH3)4, a species containing a quadruple metal-metal bond. They then study the ligand substitution chemistry of the compound to form the unbridged systems [Mo2Cl8]4- and resources.
Pence, Laura E.; Weisgerber, Amy M.; Maounis, Florence A. J. Chem. Educ. 1999, 76, 404.
Coordination Compounds |
Synthesis |
Transition Elements |
Metals |
Metallic Bonding
Ruthenium Complexes with h1-Organic Ligands: An Advanced Undergraduate Inorganic/Organometallic Chemistry Experiment  Marie P. Cifuentes, Fiona M. Roxburgh, and Mark G. Humphrey*
This experiment involves interconversions of carbene and alkenyl ligands, important monohapto ligands which are often met in an advanced undergraduate organometallic chemistry course. References are provided to extend the experiment to include alkynyl and vinylidene ligands.
Cifuentes, Marie P.; Roxburgh, Fiona M.; Humphrey, Mark G. J. Chem. Educ. 1999, 76, 401.
Organometallics |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy
Microscale Synthesis and 1H NMR Analysis of Tetraphenylporphyrins  RaeAnne E. Falvo, Larry M. Mink, and Diane F. Marsh
The synthesis of tetraphenylporphyrin, H2[TPP], and para-substituted tetraphenylporphyrins, H2[(p-X)4TPP], where X = CN, CH3, and OCH3, is easily accomplished using microscale glassware. The compounds are synthesized from inexpensive starting reagents.
Falvo, RaeAnne E.; Mink, Larry M.; Marsh, Diane F. J. Chem. Educ. 1999, 76, 237.
Instrumental Methods |
Microscale Lab |
NMR Spectroscopy |
Synthesis
An Undergraduate Experiment in Polyester (PET) Synthesis  Andrew N. Cammidge
The most important polyester manufactured industrially is PET (polyethyleneterephthalate). We describe an experiment that conveniently mimics the industrial synthesis in the undergraduate laboratory.
Cammidge, Andrew N. J. Chem. Educ. 1999, 76, 236.
Synthesis |
Equilibrium |
Stoichiometry |
Industrial Chemistry
Teaching Polymer Science to Third-Year Undergraduate Chemistry Students  Alan Jefferson* and David N. Phillips
A knowledge of the principles of polymer science is essential for graduates whose future career is certain to bring them into contact with a broad range of polymeric materials. Any undergraduate chemistry course that omits polymer chemistry and does not attempt to address and explain the principles of polymer science is lacking in relevant educational content as we approach the 21st century.
Jefferson, Alan; Phillips, David N. J. Chem. Educ. 1999, 76, 232.
Free Radicals |
IR Spectroscopy |
Synthesis
Correction to J. Chem. Educ. 1998, 75, 1641-1645  Chien M. Wai, Fred Hunt, Min Ji, and Xiaoyuan Chen
Several corrections to the original article.
Wai, Chien M.; Hunt, Fred; Ji, Min; Chen, Xiaoyuan. J. Chem. Educ. 1999, 76, 166.
Synthesis |
Organometallics
Use of Protecting Groups in Carbohydrate Chemistry: An Advanced Organic Synthesis Experiment  Anna C. Cunha, Leticia O. R. Pereira, Maria Cecília B. V. de Souza, and Vitor F. Ferreira
A simple and inexpensive three-step reaction sequence for advanced experimental organic chemistry using D-glucosamine hydrochloride as starting material for the synthesis of 2-amino-2-deoxy-1,3,4,6-tetra-O-acetyl -b-D-glucopyranose hydrochloride is described. The aim of the experiment is to protect the hydroxyl groups of D-glucosamine leaving its amino group as hydrochloride salt. The experiment deals only with protection and deprotection reactions.
Cunha, Anna C.; Pereira, Leticia O. R.; de Souza, Maria Cecília B. V.; Ferreira, Vitor F. J. Chem. Educ. 1999, 76, 79.
Carbohydrates |
Undergraduate Research |
Synthesis |
Learning Theories
Side Reactions in a Grignard Synthesis  Hilton M. Weiss
This experiment describes a standard Grignard synthesis of a secondary alcohol, 3-heptanol. It brings attention to a significant side product, 3-heptanone, and suggests ways of understanding and utilizing the formation of this product. The experiment is intended to stimulate creative thought in the undergraduate organic chemistry course.
Weiss, Hilton M. J. Chem. Educ. 1999, 76, 76.
Mechanisms of Reactions |
Synthesis |
Grignard Reagents
A Multistep Synthesis of 4-Nitro-1-ethynylbenzene Involving Palladium Catalysis, Conformational Analysis, Acetal Hydrolysis, and Oxidative Decarbonylation  Thomas E. Goodwin, Eva M. Hurst, and Ashley S. Ross
A convenient coupling procedure for the preparation of the tetrahydropyranyl ether of a propargyl alcohol derivative. This product can be easily hydrolyzed to the propargyl alcohol, then oxidatively decarbonylated to produce 4-nitro-1-ethynylbenzene. Several important topics may be illustrated and discussed in conjunction with the multistep microscale reaction series which has been developed.
Goodwin, Thomas E.; Hurst, Eva M.; Ross, Ashley S. J. Chem. Educ. 1999, 76, 74.
Microscale Lab |
Molecular Modeling |
NMR Spectroscopy |
Synthesis
A Microscale Synthesis of the Diastereomers of 2,3-Dibromosuccinic Acid  John Tomsho, James R. McKee, and Murray Zanger
Microscale procedures for the synthesis of meso- and racemic-2,3-dibromosuccinic acids are described. The methods differ from standard large-scale syntheses of these compounds and the rationale for the changes is explained.
Tomsho, John; McKee, James R.; Zanger, Murray. J. Chem. Educ. 1999, 76, 73.
Microscale Lab |
Synthesis |
Diastereomers
Micropreparation of [RuH2{P(C6H5)3}4]: A Transition Metal Hydride Compound  Donald E. Linn Jr.
A microscale laboratory is described to prepare the compounds [RuH2L(P{C6H5)3}3] (L = P(C6H5)3, H2, CO, and N2 in a pedagogical introduction to inert atmosphere inorganic syntheses.
Linn, Donald E., Jr. J. Chem. Educ. 1999, 76, 70.
Organometallics |
NMR Spectroscopy |
Microscale Lab |
Synthesis |
Transition Elements
Synthesis of Colored Superabsorbent Polymer and Its Use To Demonstrate Convection Currents in Water by Heating  Morio Takaki and Toshiyuki Itoh
Superabsorbent polymer gel is used here to exhibit a convection current of water by heating because with its high absorbent property the gel's density is almost equal to that of water. However, for good demonstration of the experiment it is necessary to use a colored polymer gel that is optimally cross-linked. The synthesis of colored polyacrylic acids for use as a new teaching material is described here.
Takaki, Morio; Itoh, Toshiyuki. J. Chem. Educ. 1999, 76, 62.
Synthesis
Reductions by the Alumino- and Borohydrides in Organic Synthesis, 2nd edition (by Jacqueline Seyden-Penne)  R. C. Hoye
This book focuses entirely on the aluminohydride and borohydride reducing agents. It condenses a large body of information into a valuable user-friendly resource for synthetic organic chemists.
Hoye, R. C. J. Chem. Educ. 1999, 76, 33.
Synthesis
Chemical Reactions in Supercritical Carbon Dioxide  Chien M. Wai, Fred Hunt, Min Ji, and Xiaoyuan Chen
Utilizing supercritical fluids as environmentally benign solvents for chemical synthesis is one of the new approaches in the "greening" of chemistry. Carbon dioxide is the most widely used gas for supercritical fluid studies because of its moderate critical constants, nontoxic nature, and availability in pure form.
Wai, Chien M.; Hunt, Fred; Ji, Min; Chen, Xiaoyuan. J. Chem. Educ. 1998, 75, 1641.
Synthesis |
Organometallics |
Reactions |
Green Chemistry |
Solutions / Solvents |
Nanotechnology |
Catalysis
The Pechmann Reaction  Michael S. Holden and R. David Crouch
A solid acid-catalyzed version of the Pechmann reaction for the synthesis of coumarins is described. The Pechmann reaction is a multiple-transformation process which is not a part of the normal organic chemistry curriculum.
Holden, Michael S.; Crouch, R. David. J. Chem. Educ. 1998, 75, 1631.
Catalysis |
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Reactions |
Phenols
Synthesis and Separation of a Diastereomeric Sulfonium Ion by Capillary Zone Electrophoresis  Francisco A. Valenzuela, Thomas K. Green, and Darwin B. Dahl
An undergraduate laboratory exercise utilizing capillary zone electrophoresis in the analysis of the student-synthesized sulfonium ion sec-butylmethyl-p-tolylsulfonium tetrafluoroborate is presented. The sulfonium ion contains two stereogenic centers and thereby yields four optical isomers.
Valenzuela, Francisco A.; Green, Thomas K.; Dahl, Darwin B. J. Chem. Educ. 1998, 75, 1590.
Electrophoresis |
Stereochemistry |
NMR Spectroscopy |
Diastereomers |
Separation Science |
Synthesis
Phase-Transfer Catalytic Reactions: A Physical Chemistry Laboratory Experiment  Nahid Shabestary, Sadegh Khazaeli, and Richie Hickman
The kinetic experiment designed here introduces many important concepts in phase-transfer catalysis and nucleophilic displacement reactions involving both mechanism and kinetics. Since this laboratory exploration includes catalytic reactions, organic synthesis, and chemical analysis, it covers many areas of chemistry.
Shabestary, Nahid; Khazaeli, Sadegh; Hickman, Richie. J. Chem. Educ. 1998, 75, 1470.
Equilibrium |
Synthesis |
Catalysis |
Kinetics
Microscale Synthesis of UO2Cl2(OPPh3)2  Francisco J. Arnáiz and Mariano J. Miranda
UO2Cl2(OPPh3)2 is a useful starting material for the preparation of other anhydrous uranyl compounds via ligand replacement. The product has been obtained by treating UO2Cl2 with OPPh3 in anhydrous ethanol.
Arniz, Francisco J.; Miranda, Mariano J. J. Chem. Educ. 1998, 75, 1457.
Coordination Compounds |
Synthesis
Characterization of the Products from the Reaction of Copper(II) Bromide and Tetramethylthiuram Sulfide: An Undergraduate Project Involving Two Unknown Metal Complexes and an Unexpected Pattern of Reactivity  Luis I. Victoriano, Hernán V. Carbacho, and Laura Parraguez
A senior undergraduate project in inorganic chemistry is described, involving the reaction of copper(II) bromide and the potential bidentate sulfur ligand bis(N,N-dimethylthiocarbamoyl) sulfide (N,N,N',N'-tetramethylthiuram monosulfide). The students are required to interpret the unusual pattern of reactivity observed, and to characterize the products generated, bromo-bis(N,N-dimethylthiocarbamoyl)sulfidocopper(I) and 2,5-bis(N,N-dimethyliminium)- 1,3,4-trithiolane tribromocuprate(I), by means of elementary analyses, infrared spectroscopy, and magnetic susceptibility measurements.
Victoriano, Luis I.; Carbacho, Hernán V.; Parraguez, Laura. J. Chem. Educ. 1998, 75, 1295.
Undergraduate Research |
Synthesis |
Coordination Compounds
Organic Reactions Involving Bromine: Puzzles for the Organic Laboratory  Sarita I. McGowens and Ernest F. Silversmith
Five puzzles for the organic chemistry laboratory are described. All involve bromine, which is generated in a safe, convenient way that makes it possible to control the amount of bromine precisely. Three of the puzzles involve orientation in electrophilic aromatic substitution, one is a determination of the stereochemistry of addition to alkenes, and the other one looks at the possibility of dehydrohalogenation following addition.
McGowens, Sarita I.; Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 1293.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions
Hetero Diels-Alder Reaction with Aqueous Glyoxylic Acid: An Experiment in Organic Synthesis and 2-D NMR Analysis for Advanced Undergraduate Students  Jacques Augé and Nadège Lubin-Germain
As an application of the use of water as solvent in organic synthesis, a convenient synthesis of a-hydroxy-g-lactones from an aqueous solution of glyoxylic acid is described. The mechanism of the reaction leading to the lactones goes through cycloadducts which rearrange in situ. The NMR analysis of the diastereomeric lactones is particularly interesting; such an analysis illustrates the importance of modern techniques including 2-D NMR spectroscopy.
Augé, Jacques; Lubin-Germain, Nadège. J. Chem. Educ. 1998, 75, 1285.
Synthesis |
NMR Spectroscopy |
Aqueous Solution Chemistry
A Modified Synthesis of the Insect Repellent DEET  Peter H. Knoess and Edward G. Neeland
In the preparation of the insect repellent DEET, lab procedures prepare the intermediate m-toluoyl chloride by heating m-toluic acid with thionyl chloride for times ranging from 15 to 45 minutes. The acid chloride is then worked up under Schotten-Baumann conditions to yield DEET.
Knoess, Peter H.; Neeland, Edward G. J. Chem. Educ. 1998, 75, 1267.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
Synthesis of NMP, a Fluoxetine (Prozac) Precursor, in the Introductory Organic Laboratory  Daniel M. Perrine, Nathan R. Sabanayagam, and Kristy J. Reynolds
A synthesis of the immediate precursor of the widely used antidepressant fluoxetine (Prozac) is described. The procedure is short, safe, and simple enough to serve as a laboratory exercise for undergraduate students in the second semester of introductory organic chemistry and is one which will be particularly interesting to those planning a career in the health sciences.
Perrine, Daniel M.; Sabanayagam, Nathan R.; Reynolds, Kristy J. J. Chem. Educ. 1998, 75, 1266.
Drugs / Pharmaceuticals |
Industrial Chemistry |
Medicinal Chemistry |
Synthesis |
Aromatic Compounds
Synthesis of Complex Natural Products as a Vehicle for Student-Centered, Problem-Based Learning  Kevin J. Cannon and Grant R. Krow
Using natural product synthesis as a vehicle, students choose a synthetic problem from the literature, identify the knowledge needed to solve the problem, explore resources for attaining that knowledge, identify the goals and criteria for a successful synthetic plan, and create and do assessments of their work.
Cannon, Kevin J.; Krow, Grant R. J. Chem. Educ. 1998, 75, 1259.
Synthesis |
Natural Products |
Undergraduate Research |
Student-Centered Learning
The Art and Science of Organic and Natural Products Synthesis  K. C. Nicolaou, E. J. Sorensen, and N. Winssinger
In this article, the history of the art and science of organic and natural products synthesis is briefly reviewed and the state of the art is discussed. The impact of this discipline on biology and medicine is amply demonstrated with examples, and projections for future developments in the field are made.
Nicolaou, K. C.; Sorensen, E. J.; Winssinger, N. J. Chem. Educ. 1998, 75, 1225.
Natural Products |
Synthesis |
Medicinal Chemistry |
Applications of Chemistry |
Drugs / Pharmaceuticals
Malaria and Red Tide Chemistry  Sabine Heinhorst and Gordon Cannon
Life cycle of mosquito that transmits malaria; do humans release pheromones?; organic synthesis of brevetoxin A, the neurotoxin of the "red tide" alga.
Heinhorst, Sabine; Cannon, Gordon. J. Chem. Educ. 1998, 75, 1207.
Synthesis |
Toxicology
A Three-Cent Reusable Craig Tube  Thomas J. Russo
A rugged three-cent reusable Craig tube is easily made from a cotton swab and disposable pipet tip. The tube costs three cents or less and can be reused.
Russo, Thomas J. J. Chem. Educ. 1998, 75, 880.
Laboratory Equipment / Apparatus |
Synthesis |
Microscale Lab
The Microscale Synthesis and Electrochemistry of Low-Valent Mononuclear Complexes (?3-C3H5)Fe(CO)3 X (X = I, Br, Cl)  Enrico Mocellin, Richard Russell, and Mauro Ravera
By combining experimental procedures which place microscale, chemical synthesis, and an inclusive, unified, product characterization in perspective, we have afforded the student the scope to obtain progressive, disciplined results and the opportunity to discuss these in the subsequent reporting.
Mocellin, Enrico; Russell, Richard; Ravera, Mauro. J. Chem. Educ. 1998, 75, 773.
Organometallics |
Microscale Lab |
Electrochemistry |
Synthesis
Modified Carbon Electrodes for Microscale Electrochemistry  Enrico Mocellin and Teresa Goscinska
This paper tries to communicate the surface chemistry nature of electrochemistry, while conveying the future possibilities and application of the subject in such a way that the students may gain some insight and venture to explore the modern methodology and its future directions.
Mocellin, Enrico; Goscinska, Teresa. J. Chem. Educ. 1998, 75, 771.
Laboratory Equipment / Apparatus |
Electrochemistry |
Microscale Lab |
Synthesis
An Efficient Microscale Procedure for the Synthesis of Aspirin  Sangeeta Pandita and Samta Goyal
We have found that aspirin can be synthesized on microscale by a simple and efficient procedure that eliminates the heating step employed in literature procedures and gives a pure, ferric-negative product (no purple color with alcoholic ferric chloride solution).
Pandita, Sangeeta; Goyal, Samta. J. Chem. Educ. 1998, 75, 770.
Microscale Lab |
Synthesis |
Drugs / Pharmaceuticals
A Microscale Synthesis of Mauve  Rhonda L. Scaccia, David Coughlin, and David W. Ball
We have reproduced Perkin's synthesis of mauve and have scaled it down to microscale levels. As such, we present a synthesis of mauve that can be performed in a microscale organic chemistry laboratory.
Scaccia, Rhonda L.; Coughlin, David; Ball, David W. J. Chem. Educ. 1998, 75, 769.
Microscale Lab |
Dyes / Pigments |
Applications of Chemistry |
Synthesis
A Convenient Apparatus for Small-Scale Dyeing with Indigo  David W. Boykin
Small fabric strips can be dyed with indigo in a simple apparatus constructed from a 50-mL filter flask. The amount of reducing agent required and the odor produced are significantly less than with open dye-bath containers.
Boykin, David W. J. Chem. Educ. 1998, 75, 769.
Dyes / Pigments |
Microscale Lab |
Synthesis |
Applications of Chemistry
S. M. Tanatar and His Contribution to the Field of Thermal Rearrangements  Ludmila Birladeanu
Thermal rearrangements constitute an important chapter in organic chemistry. Surprisingly, the name of its discoverer remains unknown. The present article is meant to remedy this situation by describing some of the work of the 19th century Russian chemist S. M. Tanatar (1849 - 1917) who, based on the thermochemical data provided by Berthelot, envisaged the possibility of transforming cyclopropane into propene under the influence of heat alone.
Birladeanu, Ludmila. J. Chem. Educ. 1998, 75, 603.
Gases |
Thermodynamics |
Synthesis |
Alkanes / Cycloalkanes |
Alkenes
Asymmetric Synthesis (by Garry Procter)  Brenda Kesler
Following an introductory chapter on the principles of asymmetric induction are seven chapters on individual classes of reactions: additions to carbonyl compounds, alpha-substitution using chiral enolates, asymmetric aldol reactions, additions to C-C double bonds, reduction and oxidation, rearrangements, and hydrolysis and esterification.
Kesler, Brenda. J. Chem. Educ. 1998, 75, 546.
Synthesis
Books Noted  Edward J. Walsh
Listing of non-reviewed books of chemical relevance.
Walsh, Edward J. J. Chem. Educ. 1998, 75, 292.
Synthesis |
Photochemistry
Book Notes: Exercises in Synthetic Organic Chemistry (by Chiara Ghiron and Russell J. Thomas)  Gretchen Rehberg
A workbook on organic synthesis is reviewed.
Rehberg, Gretchen. J. Chem. Educ. 1998, 75, 292.
Synthesis
Combinatorial Chemistry: Synthesis and Application (edited by Stephen R. Wilson and Anthony W. Czarnik)  Kevin Burgess
A book on combinatorial and medicinal chemistry is reviewed.
Burgess, Kevin. J. Chem. Educ. 1998, 75, 289.
Medicinal Chemistry |
Combinatorial Chemistry |
Synthesis
An Aldehyde Derivative  J. Hodge Markgraf and Bo Yoon Choi
A system in which aldehydes are condensed with 1,2-benzenedimethylthiol in the presence of anhydrous ferric chloride on silica gel to give 3-substituted 1,5-dihyhdro-2,4-benzodithiepines. Melting points of the derivatives were taken as a means of identification of unknown compounds.
Markgraf, J. Hodge; Choi, Bo Yoon. J. Chem. Educ. 1998, 75, 222.
Aldehydes / Ketones |
Synthesis
Grignard Synthesis of Various Tertiary Alcohols  T. Stephen Everett
A general Grignard procedure is presented for the synthesis of aliphatic, tertiary alcohols containing six to nine carbons. Without revealing the specific starting materials, students are challenged to identify their unknown products from physical (boiling points, refractive indices) and spectral (infrared O-H, C-H and fingerprint regions) data.
Everett, T. Stephen. J. Chem. Educ. 1998, 75, 86.
IR Spectroscopy |
Alcohols |
Mechanisms of Reactions |
Synthesis
A Grignard-like Organic Reaction in Water  Gary W. Breton and Christine A. Hughey
A known Grignard-like reaction between allyl bromide and benzaldehyde mediated by zinc metal in aqueous media. The procedure retains the desirable features of the traditional Grignard reaction, while eliminating some of the commonly encountered difficulties.
Breton, Gary W.; Hughey, Christine A. J. Chem. Educ. 1998, 75, 85.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Alcohols |
Synthesis |
Mechanisms of Reactions
Convenient Synthesis of a Lactone, gamma-Butyrolactone  Richard E. Bozak, J. Knittel, and Ronald J. Hicks
The synthesis of ?-butyrolactone is given.
Bozak, Richard E.; Knittel, J.; Hicks, Ronald J. J. Chem. Educ. 1998, 75, 84.
Microscale Lab |
Synthesis
Photodimerization of Anthracene  Gary W. Breton and Xoua Vang
The laboratory experiment of the photodimerization of anthracene is given.
Breton, Gary W.; Vang, Xoua. J. Chem. Educ. 1998, 75, 81.
Photochemistry |
UV-Vis Spectroscopy |
Aromatic Compounds |
Synthesis
Wohler's Urea Synthesis: Modern Version  George B. Kauffman and Steven H. Chooljian
Chemical educators who wish to have their undergraduate students repeat Wohler's urea synthesis, on of the true classics of chemistry, with modern variations and additional confirmatory tests, may consult our "modern version of a classic experiment."
Kauffman, George B.; Chooljian, Steven H. J. Chem. Educ. 1997, 74, 1493.
Synthesis
Investigation of Atropisomerism in ortho-Substituted Tetraphenylporphyrins: An Experimental Module Involving Synthesis, Chromatography, and NMR Spectroscopy  Ruth Freitag Beeston, Shannon E. Stitzel , and Mitchell A. Rhea
It is shown that as the number of cofacial methyl neighbors for a particular methyl group decreases, the chemical shift of the methyl protons increases. This experiment leads to a greater understanding of chromatography and NMR spectroscopy in addition to introducing students to porphyrin synthesis and the concepts of atropisomerism and statistical distributions.
Beeston, Ruth Freitag; Stitzel, Shannon E.; Rhea, Mitchell A. J. Chem. Educ. 1997, 74, 1468.
Instrumental Methods |
NMR Spectroscopy |
Synthesis |
Stereochemistry
The Diels-Alder Reaction of 2,4-Hexadien-1-ol with Maleic Anhydride: A Novel Preparation for the Undergraduate Organic Chemistry Laboratory Course  Keith F. McDaniel and R. Matthew Weekly
The reaction of 2,4-hexadien-1-ol with maleic anhydride provides an excellent exercise for undergraduate laboratory courses. In addition to the expected Diels-Alder reaction, which takes place readily in refluxing toluene, subsequent intramolecular cleavage of the resulting bicyclic anhydride by the pendant hydroxy group generates a lactone. Thus, two important organic reactions can be carried out in a single laboratory session.
McDaniel, Keith F.; Weekley, R. Matthew. J. Chem. Educ. 1997, 74, 1465.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Alcohols
Epoxidation of Geraniol: An Advanced Organic Experiment that Illustrates Asymmetric Synthesis  Lynn M. Bradley, Joseph W. Springer, Gregory M. Delate, and Andrew Goodman
The experiment described in this paper illustrates the principle of asymmetric epoxidation and enables students to determine enantiomeric product ratios using chiral shift reagents and NMR spectroscopy.
Bradley, Lynn M.; Springer, Joseph W.; Delate, Gregory M.; Goodman, Andrew. J. Chem. Educ. 1997, 74, 1336.
Chromatography |
NMR Spectroscopy |
Synthesis |
Stereochemistry
A Convinient Procedure for Microscale Bezoylations  Sangeeta Pandita and Samta Goyla
Benzoylation by the Schotten - Baumann method is a useful way to identify and characterize aromatic amines, phenols, sugars, etc. However, for best results, the method requires vigorous shaking in well-stoppered vessels with dropwise addition of benzoyl chloride.
Pandita, Sangeeta; Goyla, Samta. J. Chem. Educ. 1997, 74, 1335.
Microscale Lab |
Synthesis
The Preparation of T1[BF4]  Francisco J. Arnáiz
Tl[BF4], a good alternative to AgClO4, can be prepared by treating the metal or carbonate with aqueous tetrafluoroboric acid. However, the procedure outlined here, based on the reaction of thallium with hydrogen peroxide and tetrafluoroboric acid, is specially appropriate for teaching purposes.
Arnaiz, Francisco J. J. Chem. Educ. 1997, 74, 1332.
Microscale Lab |
Synthesis
Simple Preparation of Palladium(II) Complexes and Determination of Their Structures by Infrared Spectrosopy  José María Casas and Antonio Martín
The complex [PdCl2(bopy-N,O)] (1) is prepared by addition of the 2-benzoylpyridine, NC5H4 - CO - C6H5 (bopy) ligand to a refluxing suspension of PdCl2 (1:1 molar ratio). The bopy ligand is coordinated in a chelate fashion, but the Pd - O=C bond is weak and easily displaced by ligands resulting complexes cis-[PdCl2(bopy-N)(L)] (L = bopy (2), PPh3 (3)) or [NMe4][PdCl3(bopy-N)].
Casas, Jose Maria; Martin, Antonio. J. Chem. Educ. 1997, 74, 1327.
Coordination Compounds |
Group Theory / Symmetry |
IR Spectroscopy |
Synthesis
An Easy Way To Make Chlorine Water  L. H. Holmes Jr.
Chlorine water can be made easily by mixing hypochlorite and hydrochloric acid. The equilibrium lies toward Cl2 in the reaction HOCl + HCl -> Cl2 + H2O and this can be used to make chlorine water from sodium hypochlorite and hydrochloric acid if the presence of NaCl in the chlorine water does not interfere with its use.
Holmes Jr; L. H. J. Chem. Educ. 1997, 74, 1326.
Synthesis
On the Disproportionations of Cyclohexene and Related Compounds  Alex Bunjes, Ingo Eilks, Manfred Pahlke, and Bernd Ralle*
The catalytic hydrogenation of liquid hydrocarbons is easy to realize in a simple laboratory experiment using a palladium catalyst. In the case of hydrogenation cyclohexen or cyclohexadiene in addition to the expected finding of cyclohexane among the hydrogenation products, the formation of benzene can be observed. In absence of hydrogen, the disproportionation of both starting materials to cyclohexane and benzene takes place.
Bunjes, Alex; Eilks, Ingo; Pahlke, Manfred; Ralle, Bernd. J. Chem. Educ. 1997, 74, 1323.
Alkanes / Cycloalkanes |
Aromatic Compounds |
Alkenes |
Synthesis
Protecting Groups in Carbohydrate Chemistry  Sigthór Pétursson
The most important protecting groups in carbohydrate chemistry are reviewed. The paper is aimed at those beginning to specialize in synthetic carbohydrate chemistry and at teachers with other specialties who wish to go beyond the content of general organic chemistry textbooks.
Petursson, Sigthor. J. Chem. Educ. 1997, 74, 1297.
Carbohydrates |
Molecular Properties / Structure |
Synthesis
Microwave Assisted Wolff-Kishner Reduction Reaction  Eric Parquet and Qun Lin
The two step syntheses described here offer several advantages: (1) very short reaction time with no need for special microscale glassware, (2) mild experimental conditions (hot oil baths and heating mantles are not required), (3) the reagents are easy to handle.
Parquet, Eric; Lin, Qun. J. Chem. Educ. 1997, 74, 1225.
Synthesis |
Microscale Lab
Regioselective Hydrochlorination: An Experiment for the Undergraduate Laboratory  Philip Boudjouk, Beon-Kyu Kim, and Byung-Hee Han
A simple and convenient procedure for the addition of hydrogen chloride to a variety of olefins is described. Conventional glassware is used and product isolation is straightforward using distillation techniques.
Boudjouk, Philip; Kim, Beon-Kyu; Han, Byung-Hee. J. Chem. Educ. 1997, 74, 1223.
Learning Theories |
NMR Spectroscopy |
Synthesis |
Electrophilic Substitution
Ozonolysis Experiments Using Gas Chromatography-Mass Spectrometry: An Undergraduate Organic Chemistry Laboratory Experiment  Charlene M. Rhoads, George R. Farquar, and William F. Wood
A general method was developed for undergraduate laboratory instruction using ozonolysis at room temperature followed by gas chromatography-mass spectrometry (GC-MS). The simple ozonolysis apparatus described can be constructed from material found in most chemistry laboratories.
Rhoads, Charlene M.; Farquar, George R.; Wood, William F. J. Chem. Educ. 1997, 74, 1220.
Mechanisms of Reactions |
Microscale Lab |
Synthesis |
Spectroscopy |
Gas Chromatography |
Mass Spectrometry
Kinetic versus Thermodynamic Control in the Dehydration of 2-Methylcyclopentanol: A Two-Part Laboratory Experiment Utilizing the Gignard Reaction and GC-MS  Thomas Poon, Bradford P. Mundy, Jean McIntyre, Lesley Woods, Frank G. Favaloro Jr., and Christina A. Goudreau
A two part organic laboratory experiment illustrating the Grignard reaction and the concept of kinetic versus thermodynamic control is described. The dehydration is monitored by GC/MS and the experiment can be performed using macro and microscale techniques.
Poon, Thomas; Mundy, Bradford P.; MnIntyre, Jean; Woods, Lesley; Favaloro Jr.; Frank G.; Goudreau, Christina A. J. Chem. Educ. 1997, 74, 1218.
Chromatography |
Synthesis |
Gas Chromatography |
Mass Spectrometry |
Grignard Reagents
Methylation of Isobutyrophenone Using Potassium Triphenylmethide: An Advanced Organic Chemistry Laboratory Experiment  Fred J. Matthews
A detailed description of an alkylation reaction of isobutyrophenone using tritylpotassium as base. The reaction involves use of moisture sensitive reactants and intermediates under an inert atmosphere and is best suited for an advanced organic chemistry laboratory.
Matthews, Fred J. J. Chem. Educ. 1997, 74, 996.
Synthesis
The Gravimetric Analysis of Nickel Using a Microwave Oven  Nadia Carmosini, Sanaz Ghoreshy, Marina C. Koether
The procedure for the gravimetric quantitative analysis of the percent of nickel in steel has been modified to include the use of a microwave oven. The microwave oven proved to be very useful for time efficiency.
Carmosini, Nadia ; Ghoreshy, Sanaz; Koether, Marina C. J. Chem. Educ. 1997, 74, 986.
Gravimetric Analysis |
Synthesis |
Quantitative Analysis
Synthesis of 4-Nitro-1-Pentynylbenzene: An Example of Transitional Metal-Mediated Cross-Coupling  Ronald G. Brisbois, William G. Batterman, and Scott R. Kragerud
Synthesis of the target compound exemplifies contemporary Pd-mediated cross-coupling methodologies. In this regard, several fundamental mechanistic aspects of catalytic organometallic chemistry are illustrated, including oxidative addition, transmetallation, and reductive elimination.
Brisbois, Ronald G. ; Batterman, William G.; Kragerud, Scott R. J. Chem. Educ. 1997, 74, 832.
Synthesis |
Microscale Lab |
Organometallics |
Transition Elements |
Aromatic Compounds
Chemistry Under Extreme or Non-Classical Conditions  reviewed by William J. le Noble
Topics include "Chemical Synthesis Using High Temperature Species", "Effect of Pressure on Inorganic Reactions", "Organic Synthesis at High Pressure", "Inorganic and Related Chemical Reactions in Supercritical Fluids", "Organic Chemistry in Supercritical Fluids", "Ultrasound as a New Tool for Synthetic Chemists", "Applications of High Intensity Ultrasound in Polymer Chemistry", "Microwave Dielectric Heating Effects in Chemical Synthesis", and "Biomolecules Under Extreme Conditions".
le Noble, William J. J. Chem. Educ. 1997, 74, 764.
Synthesis
Simple Synthesis and Use of a Nickel Alkene Isomerization Catalyst. An Advanced Lab in Inorganic/Organometallic Chemistry  Kurt R. Birdwhistell and Joann Lanza
In this laboratory experiment students synthesize a precatalyst, [Ni(P(OEt)3)4]. The precatalyst is protonated insitu to make [HNi(P(OEt)3)4]+, a nickel hydride, which is an active catalyst for alkene isomerization. Students produce the nickel hydride in the presence of 1-heptene at 0C and monitor the extent of heptene isomerization by gas chromatography as a function of time. Students use this data to assess the effectiveness of their catalyst.
Birdwhistell, Kurt R.; Lanza, Joann. J. Chem. Educ. 1997, 74, 579.
Catalysis |
Coordination Compounds |
Organometallics |
Synthesis
The Synthesis, Characterization, and Lewis Acidity of SnI2 and SnI4  Richard W. Schaeffer, Benny Chan, Michael Molinaro, Susan Morissey, Claude H. Yoder, Carolyn S. Yoder, and Stephanie Shenk
In this project the student has the opportunity to learn about: a) the direct synthesis of compounds from the elements, b) stoichiometry and limiting reagent, c) isolation by recrystallization, d) use of inert atmosphere, e) identification by melting point, gravimetric analysis, powder x-ray diffraction, and NMR spectroscopy, and f) at least one method for determination of relative Lewis acidity.
Schaeffer, Richard W. ; Chan, Benny ; Molinaro, Michael; Morissey, Susan ; Yoder, Claude H.; Yoder, Carolyn S.; Shenk, Stephanie. J. Chem. Educ. 1997, 74, 575.
Acids / Bases |
Synthesis |
Stoichiometry |
Lewis Acids / Bases |
NMR Spectroscopy
Sheldon Shore, Small Boranes, and Ammonia  Robert W. Parry
The paper discusses the early studies on "the diammoniate of diborane" and emphasizes how continuing work done by Sheldon Shore at Ohio State University extended the work on the boranes and answered here-to-fore vexing structural problems on intermediates in the borane and borane-ammonia system.
Parry, Robert W. J. Chem. Educ. 1997, 74, 512.
Acids / Bases |
Coordination Compounds |
Crystals / Crystallography |
Synthesis
The Wittig Reaction: Generation, Observation and Reactivity of a Phosphorous Ylide Intermediate. An Experiment for the Advanced Organic Chemistry Laboratory Course  Gary W. Breton
An experiment has been devised that illustrates three important concepts in organic chemistry: the synthesis of an alkene via the Wittig reaction, characterization of a reactive intermediate by 1H NMR, and site - specific deuterium labeling.
Breton, Gary W. J. Chem. Educ. 1997, 74, 114.
Synthesis |
Alkenes |
NMR Spectroscopy
A -78°C Sequential Michael Addition for the Organic Lab  Michael W. Tanis
This paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions.
Tanis, Michael W. J. Chem. Educ. 1997, 74, 112.
Addition Reactions |
Alkenes |
Aldehydes / Ketones |
Synthesis
Preparation and Solution Polymerization of Diacetylenes  Bruce A. Hathaway and Angela M. Scates
Most published student laboratory syntheses of symmetrical diacetylenes follow Hay's procedure, with some modifications for using air as a source of oxygen. We report a simpler procedure, which has been useful in preparing a variety of diacetylenes. In addition, we have developed conditions suitable for solution polymerization of these diacetylenes to PDA's, using short-wave UV light.
Hathaway, Bruce A.; Scates, Angela M. J. Chem. Educ. 1997, 74, 111.
Synthesis |
Alkenes
The Synthesis of a Superabsorbent Polymer  Charles M. Garner, Matthew Nething, and Phuc Nguyen
The preparation and mode of action of a superabsorbent polymer is described. The material consists of lightly crosslinked, mostly neutralized polyacrylic acid which can be prepared using either a redox or a thermal radical initiator. The resulting polymer absorbs 500-3000 times its weight in distilled water, depending on the degree of crosslinking employed.
Garner, Charles M.; Nething, Matthew; and Nguyen, Phuc . J. Chem. Educ. 1997, 74, 95.
Synthesis
Generation of HCl, DCl, HBr, and DBr (the author replies)  Ganapathisubramanian, N.
Procedure is to generate HCl, DCl, HBr, and DBr simultaneously.
Ganapathisubramanian, N. J. Chem. Educ. 1996, 73, A260.
Synthesis |
Nuclear / Radiochemistry
Generation of HCl, DCl, HBr, and DBr  Bader, Morris
Previous JCE articles on this topic.
Bader, Morris J. Chem. Educ. 1996, 73, A260.
Synthesis |
Nuclear / Radiochemistry
Generation of HCl, DCl, HBr, and DBr  Bader, Morris
Previous JCE articles on this topic.
Bader, Morris J. Chem. Educ. 1996, 73, A260.
Synthesis |
Nuclear / Radiochemistry
The Synthesis of [Pd(mu-Cl)(C6H4N=NPh)]2  Arnaiz, Francisco J.
The procedure proposed in this article consists of reacting PdCl2 with azobenzene in dimethyl sulfoxide (DMSO) and is appropriate especially for the microscale laboratory because it offers some advantages with respect to previously reported procedures.
Arnaiz, Francisco J. J. Chem. Educ. 1996, 73, A126.
Synthesis |
Microscale Lab |
Organometallics
Preparation and Properties of a Stable Organic Cation: A Microscale Experiment for Organic Chemistry  K. P. Manfredi and L. A. McGrew
This article describes the microscale synthesis and characterization of the flavylium cation. It is a suitable experiment for students in the second semester of organic chemistry laboratory.
Manfredi, K. P.; McGrew, L. A. J. Chem. Educ. 1996, 73, A124.
Synthesis |
Microscale Lab |
NMR Spectroscopy
The Synthesis of 10-[Spiro[6,6]C60]-Anthrone: A Microscale Reaction of Fullerene  John Almy, Antonio Herrera, and Nazario Martín
The microscale 1,3-dipolar cycloaddition reaction of Fullerene-C60 with 10-diazoanthrone leading to the methanofullerene adduct is described. The synthesis of the monoadduct and flash chromatography separation of the formed bisadducts was set up for two three hour laboratory periods.
Almy, John; Herrera, Antonio; Martin, Nazario; Seoane, Carlos; Suzuki, Toshiyasu; Wudl, Fred. J. Chem. Educ. 1996, 73, A105.
Synthesis |
Chromatography |
Microscale Lab
Inexpensive Small-Scale Sonochemistry with Magnetic Agitation  Fernando G. Braga
A reduction, esterification, acetylation, an ether synthesis, and an aryl nucleophilic substitution are performed in a microwave oven.
Braga, Fernando G. J. Chem. Educ. 1996, 73, A104.
Microscale Lab |
Synthesis |
Mechanisms of Reactions
Microwave Microscale Organic Experiments  John W. Elder and Kathleen M. Holtz
This article describes an inexpensive apparatus to perform sonochemical reactions, in small scale, using common lab glassware.
Elder, John W.; Holtz, Kathleen M. J. Chem. Educ. 1996, 73, A104.
Microscale Lab |
Magnetic Properties |
Laboratory Equipment / Apparatus |
Synthesis
Grignard Reaction of an Epoxide: A Mechanistic Study  James A. Ciaccio, Sabrina Volpi, Ransford Clarke
Unlike most undergraduate Grignard experiments which are performed merely for the sake of illustrating a textbook reaction, this Grignard synthesis is performed to probe the reactivity of styrene oxide. Students are required to analyze their products by TLC and NMR spectroscopy (instead of just submitting them for a grade) in order to obtain the data necessary for making mechanistic conclusions.
Ciaccio, James A.; Volpi, Sabrina; Clarke, Ransford. J. Chem. Educ. 1996, 73, 1196.
Grignard Reagents |
Epoxides |
Thin Layer Chromatography |
NMR Spectroscopy |
Synthesis
Microscale Synthesis and Electronic Absorption Spectroscopy of Tetraphenylporphyrin H2(TPP) and Metalloporphyrins ZnII(TPP) and NiII(TPP)  Diane F. Marsh, Larry M. Mink
The microscale syntheses of Tetraphenylporphyrin, H2(TPP), and the corresponding metalloporphyrins ZnII(TPP) and NiII(TPP) are reported. H2(TPP) is synthesized by the condensation of benzaldehyde and pyrrole, and the subsequent metallation of H2(TPP) is achieved with anhydrous ZnIICl2 or NiIICl2 in DMF.
Marsh, Diane F.; Mink, Larry M. J. Chem. Educ. 1996, 73, 1188.
Microscale Lab |
Synthesis |
Coordination Compounds
Use of Infrared Spectroscopy in Monitoring a New Method for the Preparation of Sulotroban, an Antithrombotic Drug: A Medicinal Chemistry Experiment  Alain Nuhrich, Martine Varache-Lembège, Fabrice Martin, Guy Devaux,
The chemical experimental procedures given integrate an infrared spectroscopy technique for monitoring the chromatographic purification processes used in this synthesis. The purpose of the proposed manipulations is to reflect in a concrete manner the reality of doing research on and preparing drugs of chemical origin.
Nuhrich, Alain; Varache-Lembège, Martine; Lacan, Fabrice; Devaux, Guy. J. Chem. Educ. 1996, 73, 1185.
IR Spectroscopy |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis |
Aromatic Compounds
Microscale Preparation of Difluorenylidene and trans-2,3-Dibenzoylspiro[cyclopropane-1-99-fluorene]  Fred H. Greenberg
The synthetic sequence involving the oxidation of fluorene to fluorenone and the reduction of fluorenone to fluorenol can be extended by preparing the title compounds via the intermediate 9-chlorofluorene. The latter is obtained by heating fluorenol in methanol with conc. hydrochloric acid.
Greenberg, Fred H. J. Chem. Educ. 1996, 73, 1043.
Synthesis |
Aromatic Compounds
Synthesis of N-Methyl-2-trichloroacetylpyrrole-A Key Building Block in Peptides That Bind DNA: Micro-, Semimicro-, and Macro-Scale Organic Lab Experiments  Michael D. Mosher, Erik J. Verner, Bradford J. Oliver, Daniel Hamlin, Nicholas Vietri, Robert B. Palmer, Tyrone V. Arnold, Nicholas R. Natale
The repeating pyrrole unit contained in netropsin and distamycin can be prepared from N-methylpyrrole via a noncatalyzed Friedel-Crafts acylation. The reaction has been adapted for use in the undergraduate organic chemistry laboratory on three different scales: microscale, semimicroscale, and macroscale.
Mosher, Michael D.; Verner, Erik J.; Oliver, Bradford J.; Hamlin, Daniel; Vietri, Nicholas; Palmer, Robert B.; Arnold, Tyrone V.; Natale, Nicholas R. J. Chem. Educ. 1996, 73, 1036.
Synthesis |
Proteins / Peptides |
Microscale Lab
The Synthesis of Proteins-A Simple Experiment To Show the Procedures and Problems of Using Radioisotopes in Biochemical Studies  David M. Hawcroft
The experiment described in this paper uses simple techniques to illustrate the procedures involved in working with radioisotopes when following a simplified metabolic pathway. Safety considerations are discussed and a list of safety rules is provided, but the experiment itself uses very low levels of a weak beta-emitting isotope (tritium).
Hawcroft, David M. J. Chem. Educ. 1996, 73, 1030.
Proteins / Peptides |
Synthesis |
Nuclear / Radiochemistry
Novel Preparation of a Tetraaza Macrocycle: An Advanced Inorganic Chemistry Laboratory  Jerry W. Hayes II, Cynthia J. Taylor, Richard P. Hotz
The microwave oven synthesis of a sterically congested macrocycle 6,8,15,17-tetraphenyldibenzo[b,i][1,4,8,11] tetraazacyclotetradecinato nickel(II), abbreviated [Ni(Ph4Bzo2[14]tetraeneN4)], is presented as an advanced inorganic chemistry laboratory.
Hayes II, Jerry W.; Taylor, Cynthia J.; Hotz, Richard P. J. Chem. Educ. 1996, 73, 991.
Coordination Compounds |
Transition Elements |
NMR Spectroscopy |
Quantitative Analysis |
Synthesis
A Convenient Synthesis of the Tetrasubstituted Pyrrole: An Undergraduate Heterocyclic Laboratory Experiment  Patrik Kolar, Miha Tisler
A two-step synthesis of tetrasubstituted pyrroles from esters of a-amino acids has been applied as a simple undergraduate laboratory experiment, which illustrates the utility of amino acids in heterocyclic synthesis.
Kolar, Patrik; Tisler, Miha. J. Chem. Educ. 1996, 73, 986.
Amino Acids |
IR Spectroscopy |
Synthesis |
Heterocycles |
Esters
CAChe Molecular Modeling: A Visualization Tool Early in the Undergraduate Chemistry Curriculum  R. David Crouch, Michael S. Holden, and Cindy Samet
In Dickinson's chemistry curriculum, "Synthesis & Reactivity" replaces the traditional organic chemistry sequence and begins in the second semester of the freshman year. A number of "Synthesis & Reactivity" experiments have been developed that include an out-of-class computational chemistry exercise using CAChe, a versatile molecular modeling software package.
Crouch, R. David; Holden, Michael S.; Samet, Cindy. J. Chem. Educ. 1996, 73, 916.
Molecular Modeling |
Synthesis
Wöhler's Synthesis of Urea: How Do the Textbooks Report It?  Paul S. Cohen and Stephen M. Cohen
Most general chemistry and organic chemistry textbooks describe Friedrich Whler's synthesis of urea as the moment when modern organic chemistry was born. We surveyed 35 modern and classic texts to learn what each noted of Whler's work
J. Chem. Educ. 1996, 73, 883.
Synthesis
"Course Thesis" as End of the Laboratory Experimental Program  Alexandre A. Dobrev
The "course thesis" is introduced as end of the laboratory experimental program for the students in organic chemistry and consists of two- or three-step synthesis of an organic compound for which good procedures for synthesis are described in the literature.
J. Chem. Educ. 1996, 73, 856.
Synthesis
Useful Spreadsheet for Updating Multistep Organic Synthesis  Pedro Ortega, Miguel Guzmán, and Leonel Vera
188. The design of a spreadsheet that allows one to update the required stoichiometric relationships for a multistep synthesis, and how to interconnect the steps and scale up all the chemicals needed for preparation.
Ortega, Pedro A.; Guzman, Miguel E.; Vera, Leonel. J. Chem. Educ. 1996, 73, 726.
Synthesis |
Stoichiometry |
Laboratory Management
Cascade Sequences in Organic Synthesis: A Lesson from Nature?  Shelagh T. Dennison and David C. Harrowven
This article addresses the attempts of synthetic chemists to mimic nature's syntheses of terpene natural products in the laboratory.
Dennison, Shelagh T.; Harrowven, David C. J. Chem. Educ. 1996, 73, 697.
Synthesis |
Applications of Chemistry |
Mechanisms of Reactions |
Natural Products
Chemoenzymatic Synthesis of an Enantiomerically Pure Lactone: A Three-Step Synthesis for Undergraduate Organic Chemistry Laboratory  Cynthia K. McClure and H. Keith Chenault
A three-step laboratory sequence for the undergraduate organic laboratory is described. This series of experiments requires a student to use the product from one reaction as the starting material for a subsequent reaction, and thus the affords the student a "real world" experience of multistep synthesis.
McClure, Cynthia K.; Chenault, H. Keith. J. Chem. Educ. 1996, 73, 467.
Synthesis |
Catalysis |
Enzymes |
IR Spectroscopy
Synthesis and Kinetics of Hydrolysis of 3,5-Dimethyl-N-acetyl-p-benzoquinone Imine: An Undergraduate Laboratory  Jeanne M. Buccigross, Christa Metz, Lori Elliot, Pamela Becker, Angela S. Earley, Jerry W. Hayes, Michael Novak, and Gayl A. Underwood
The synthesis of the title compound by a three-step procedure is described. The hydrolysis kinetics, which involve two consecutive psuedo-first-order processes, are also described.
Buccigross, Jeanne M.; Metz, Christa; Elliot, Lori; Becker, Pamela; Earley, Angela S.; Hayes, Jerry W.; Novak, Michael; Underwood, Gayl A. J. Chem. Educ. 1996, 73, 364.
Synthesis |
Kinetics |
UV-Vis Spectroscopy
COS: Organic Reaction Drills Based Upon Collective Organic Syntheses  Victor I. Bendall
The eight volumes of Collective Organic Syntheses contain about 2200 recipes for the production of high quality compounds acceptable yields. The COS software allows students to test their knowledge of these reaction sequences.
Bendall, V. I. . J. Chem. Educ. 1996, 73, 323.
Synthesis
Disconnect by the Numbers: Protocol for the Synthesis of Alkanes  Michael B. Smith
This addendum gives a method to convert an alkane to a functionalized precursor and that new molecule can be analyzed in the normal manner. --------------------------------------------------------------------------------
Smith, Michael B. J. Chem. Educ. 1996, 73, 304.
Alkanes / Cycloalkanes |
Synthesis
Convergent Synthesis of Betaine-30, a Solvatochromic Dye: An Advanced Undergraduate Project and Demonstration  Bruce R. Osterby and Ronald D. McKelvey
Solvatochromism is used to describe a pronounced change in the position of a UV-Vis absorption band with a change in solvent polarity.
Osterby, Bruce R.; McKelvey, Ronald D. J. Chem. Educ. 1996, 73, 260.
Dyes / Pigments |
Synthesis |
Solutions / Solvents |
UV-Vis Spectroscopy
Synthesis of Ethyl Salicylate Using Household Chemicals  Sally Solomon, Chinhyu Hur, Alan Lee, and Kurt Smith
Ethyl salicylate is synthesized, isolated, and characterized in a three-step process using simple equipment and household chemicals.
Solomon, Sally; Hur, Chinyu; Lee, Alan; Smith, Kurt. J. Chem. Educ. 1996, 73, 173.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
The Formation of Urea: Controversies and Confusion  Marten J. ten Hoor
This paper gives detailed information about the synthesis and many other interesting aspects of urea chemistry that are often overshadowed by the discussion of its historical import.
ten Hoor, Marten J. J. Chem. Educ. 1996, 73, 42.
Synthesis
Photochemical Key Steps in Organic Synthesis: An Experimental Course Book  reviewed by Roger C. Hahn
Photochemical organic synthesis experiments.
Hahn, Roger C. J. Chem. Educ. 1995, 72, A229.
Photochemistry |
Synthesis
Selective and Quantitative Catalytic Hydrogenation: A Safe, Inexpensive Experiment for Large Classes  John A. Landgrebe
A catalytic hydrogenation experiment suitable for large classes.
Landgrebe, John A. J. Chem. Educ. 1995, 72, A220.
Catalysis |
Synthesis |
Laboratory Equipment / Apparatus |
Microscale Lab
Microscale Preparation of Nickel Formate Dihydrate: A Simple Experiment for the Freshman Lab  Arnaiz, Francisco J.
Microscale preparation of nickel formate dihydrate.
Arnaiz, Francisco J. J. Chem. Educ. 1995, 72, A200.
Metals |
Gravimetric Analysis |
Synthesis
An Efficient Microscale Procedure for the Preparation of 3,5-Dinitrobenzoates  Smith, Richard F.; Cristalli, Gaetano M.
Efficient and simple microscale preparation of 3,5-dinitrobenzoates.
Smith, Richard F.; Cristalli, Gaetano M. J. Chem. Educ. 1995, 72, A164.
Synthesis |
Qualitative Analysis |
Laboratory Management |
Microscale Lab |
Aromatic Compounds |
Esters
Principles of Organic Synthesis, Third Edition (Norman, Richard O.C.; Coxon, James M.)  Bank, Shelton
A two-part introduction to organic synthesis for students who have completed the traditional sophomore organic chemistry introductory course or its functional equivalent.
Bank, Shelton J. Chem. Educ. 1995, 72, A152.
Synthesis
Organic Syntheses. Collective Volumes 1-8, Cumulative Indices (Freeman, Jeremiah P.)  
Title of interest.
J. Chem. Educ. 1995, 72, A126.
Synthesis
Microscale Ninhydrin Test Applied to Solid-Phase Peptide Synthesis  Vilaseca, Lluis; Bardaji, Eduard
A modification of the ninhydrin test that allows the use of very small portions of peptide-resins and reagents and employs melting point tubes.
Vilaseca, Lluis; Bardaji, Eduard J. Chem. Educ. 1995, 72, A99.
Amino Acids |
Proteins / Peptides |
Laboratory Equipment / Apparatus |
Synthesis
Organic Reactions, Volume 45 (Paquette, Leo A.)  
Continuing series.
J. Chem. Educ. 1995, 72, A94.
Synthesis |
Reactions
Fieser and Fieser's Reagents for Organic Synthesis, Volume 17 (Fieser, Mary)  
Continuing series.
J. Chem. Educ. 1995, 72, A94.
Synthesis
Tetrahedron Organic Chemistry Series. Volume 11, Organic Syntheses Based on Name Reactions and Unnamed Reactions (Hassner, A.; Stumer, C.; Baldwin, J. E.; Magnus, P. D.)  
Continuing series.
J. Chem. Educ. 1995, 72, A94.
Synthesis
Tetrahedron Organic Chemistry Series. Volume 12, Enzymes in Synthetic Organic Chemistry (Wong, Chi-Huey, Whitesides, George M.; Baldwin, J. E.; Magnus, P. D.)  
Continuing series.
J. Chem. Educ. 1995, 72, A94.
Synthesis |
Enzymes
Discovery-Based Microscale Catalytic Decarbonylation of Aldehydes  Pearsall, Mary-Ann; Rosen, Alan M.; Conrad, Jennifer S.; Hendrickson, Carrie A.; Pacchia, Ann Marie L.; Schantz, Daniel J.
Experimental procedure for decarbonylation of aldehydes by heating over a palladium/carbon catalyst.
Pearsall, Mary-Ann; Rosen, Alan M.; Conrad, Jennifer S.; Hendrickson, Carrie A.; Pacchia, Ann Marie L.; Schantz, Daniel J. J. Chem. Educ. 1995, 72, A29.
Synthesis |
Catalysis |
Aldehydes / Ketones |
Microscale Lab
Microscale Synthesis of the Natural Products Carpanone and Piperine  Sloop, Joseph C.
Experimental procedure for synthesizing carpanone and piperine.
Sloop, Joseph C. J. Chem. Educ. 1995, 72, A25.
Synthesis |
Microscale Lab |
Ethers
Tactics of Organic Synthesis (Ho, Tse-Lok)  
Monograph.
J. Chem. Educ. 1995, 72, A19.
Synthesis
Microscale Electrophilic Aromatic Substitution of p-Toluidine  Kady, Ismail O.
Experimental procedure for first-year organic chemistry students to apply the principles of group protection and study the effect of ring substituents on reaction orientation.
Kady, Ismail O. J. Chem. Educ. 1995, 72, A9.
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Microscale Lab |
Electrophilic Substitution
Microscale Preparation of AlCl3  Arnaiz, Francisco J.
Experimental procedure for producing anhydrous AlCl3 (aluminum chloride).
Arnaiz, Francisco J. J. Chem. Educ. 1995, 72, A8.
Synthesis |
Laboratory Management |
Microscale Lab
Microscale Synthesis of MoO2(acac)2  Arnaiz, Francisco J.
Experimental procedure for improving the synthesis of MoO2(acac)2 (acac = 2,4-pentanedionate).
Arnaiz, Francisco J. J. Chem. Educ. 1995, 72, A7.
Synthesis |
Laboratory Management |
Microscale Lab
Baeyer-Villiger Oxidation of Indane-1-ones: Monitoring of the Reaction by VPC and IR Spectroscopy  Elie Stephan
Procedure for the Baeyer-Villiger oxidation of indane-1-ones.
Stephan, Elie. J. Chem. Educ. 1995, 72, 1142.
IR Spectroscopy |
Synthesis |
Mechanisms of Reactions |
Oxidation / Reduction |
Aldehydes / Ketones
Letters  
Reference to a modern version of the classic experiment.
J. Chem. Educ. 1995, 72, 1055.
Synthesis |
Microscale Lab
An Analysis of the Involvement of Purine Ribonucleotides in Eukaryotic Protein Synthesis: An Undergraduate Biochemistry Laboratory Experiment  T. Glen Lawson
Experimental procedure in which students can study directly the chemical mechanisms involved in the synthesis of proteins by cellular messenger RNA translation systems.
Lawson, T. Glen. J. Chem. Educ. 1995, 72, 1041.
Proteins / Peptides |
Synthesis
Synthesis of a Bromohydrin: An Experiment Demonstrating Markovnikov Addition  Diane J. Porter, Andrea T. Stewart, and Carl T. Wigal
Microscale procedure that demonstrates Markovnikov addition without the production of noxious products (i.e. mercury).
Porter, Diane J.; Stewart, Andrea T.; Wigal, Carl T. J. Chem. Educ. 1995, 72, 1039.
Mechanisms of Reactions |
Synthesis |
Microscale Lab |
Microscale Lab
Diastereospecific Synthesis of an Epoxide: An Introductory Experiment in Organic Synthetic and Mechanistic Chemistry  James A. Ciaccio
A two-step epoxide synthesis that can be presented to students in the form of two mechanistic "puzzles" that probe the stereoselectivity of two important reactions: halohydrin formation from alkenes and epoxide formation via intramolecular Williamson ether synthesis.
Ciaccio, James A. J. Chem. Educ. 1995, 72, 1037.
Stereochemistry |
Molecular Properties / Structure |
Mechanisms of Reactions |
Synthesis |
Epoxides |
Alkenes
Template Synthesis of Macrocyclic Complexes: A Laboratory Project for Advanced Undergraduate Students  James H. Cameron
Procedure for template synthesis of a macrocyclic (Jager) complex.
Cameron, James H. J. Chem. Educ. 1995, 72, 1033.
Synthesis |
Coordination Compounds |
Organometallics |
Mechanisms of Reactions
Other Publications on C6Cl6 and C2Cl6  Keiter, Richard L.
Previous JCE articles on the formation of C6Cl6 and C2Cl6.
Keiter, Richard L. J. Chem. Educ. 1995, 72, 956.
Synthesis
Infrared Spectroscopy: A Versatile Tool in Practical Chemistry Courses   Volker Wiskam, Wolfgang Fichtner, Volker Kramb, Alexander Nintschew, and Jens Stefan Schneider
Procedure for preparing samples of basic inorganic compounds and analyzing them through IR spectroscopy in freshman chemistry.
Wiscamp, Volker; Fichtner, Wolfgang; Kramb, Volker; Nintschew, Alexander; Schneider, Jens Stefan. J. Chem. Educ. 1995, 72, 952.
IR Spectroscopy |
Synthesis |
Coordination Compounds
Synthesis and Variable-Temperature 1H NMR Conformational Analysis of Bis(eta5-cyclopentadienyl)titanium Pentasulfide: An Experiment for an Integrated, Advanced Laboratory Course  Anthony Diaz, Catherine Radzewich, and Mark Wicholas
An integrated advanced inorganic and physical chemistry laboratory.
Diaz, Anthony; Radzewich, Catherine; Wicholas, Mark. J. Chem. Educ. 1995, 72, 937.
NMR Spectroscopy |
Organometallics |
Synthesis
Synthesis and Characterization of Potassium Tris(oxalato)ferrate(III) Trihydrate: A Spectrophotometric Method of Iron Analysis  Richard F. Dallinger
A general chemistry experiment that combines titrimetric, gravimetric, and spectrophotometric analysis in two, three-hour lab periods.
Dallinger, Richard F. J. Chem. Educ. 1995, 72, 936.
Spectroscopy |
Synthesis |
Titration / Volumetric Analysis |
Gravimetric Analysis
The AC Rule: An Algorithm for Organic Reactions  Edgar F. Kiefer
Algorithm for predicting organic reaction mechanisms.
Kiefer, Edgar F. J. Chem. Educ. 1995, 72, 906.
Mechanisms of Reactions |
Synthesis |
Reactions
Regioselective Methoxybromination of Styrene Using TBABr3 in Methanol: An Organic Laboratory Experiment   Jacques Berthelot, Yamina Benammar, and Catherine Lange
Methoxybromination of styrene using TBABr3 in methanol.
Bertholet, Jacques; Benammar, Yamina; Lange, Catherine. J. Chem. Educ. 1995, 72, 850.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Addition Reactions
The Addition of Hydrogen Bromide to Simple Alkenes  Hilton M. Weiss
Synthesis of 1-bromohexane.
Weiss, Hilton M. . J. Chem. Educ. 1995, 72, 848.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Alkenes
A Convenient, One-Step Synthesis of YBa2CU3O7-x Superconductors: An Undergraduate Inorganic/Materials Laboratory Experiment  Connie D. Cogdell, Darcey G. Wayment, Dominick J. Casadonte, Jr., and Kim A. Kubat-Martin
A materials-oriented lab designed to provide students with the skills necessary for the fabrication of modern materials (a copper oxide superconductor).
Cogdell, Connie D.; Wayment, Darcey G.; Casadonte, Dominick J., Jr.; Kubat-Martin, Kim A. J. Chem. Educ. 1995, 72, 840.
Metals |
Superconductivity |
Materials Science |
Synthesis
Synthesis and Decomposition of Zinc Iodide: Model Reactions for Investigating Chemical Change in the Introductory Laboratory  Stephen DeMeo
Procedure for synthesizing and then decomposing zinc iodide in introductory chemistry that offers advantages over traditional synthesis/decomposition species (e.g. copper sulfide and magnesium oxide).
DeMeo, Stephen. J. Chem. Educ. 1995, 72, 836.
Synthesis |
Thermodynamics |
Reactions
Oxomolybdenum Chemistry: An Experiment   Charles G. Young
Experiment involving the synthesis and characterization of several oxomolybdenum complexes and the exploration of a historically important system for catalytic oxygen transfer.
Young, Charles G. J. Chem. Educ. 1995, 72, 751.
Metals |
Organometallics |
Coordination Compounds |
Synthesis |
Catalysis
Mass Spectrometry for Large Undergraduate Laboratory Sections  A. Illies, P. B. Shevlin, G. Childers, M. Peschke and J. Tsai
A gas chromatography - mass spectrometry experiment that allows each student in a large laboratory class to analyze the products of a simple organic synthesis.
Illies, A.; Shevlin, P. B.; Childers, G.; Peschke, M.; Tsai, J. J. Chem. Educ. 1995, 72, 717.
Mass Spectrometry |
Chromatography |
Synthesis |
Separation Science |
Gas Chromatography
Propylene Oxide Addition to Hydrochloric Acid: A Textbook Error  Rebecca E. Phillips and Robert L. Soulen
Procedure illustrating organic synthesis involving propylene oxide, a major industrial chemical, and important features of the SN1 and SN2 mechanisms (there are some differences on how this reaction is described in several organic textbooks).
Phillips, Rebecca E.; Soulen, Robert L. J. Chem. Educ. 1995, 72, 624.
Synthesis |
Mechanisms of Reactions |
Nucleophilic Substitution
A Centenary Synthesis of Carone and Dicarvelone  Armstead, D. E. F.
Procedure for synthesizing carone and dicarvelone.
Armstead, D. E. F. J. Chem. Educ. 1995, 72, 550.
Synthesis |
Aldehydes / Ketones
Charge Distribution in 1,1-Dicyano-2-Arylethenes: An Undergraduate Organic Experiment Utilizing the Knoevenagel Condensation and NMR Spectroscopy  Rowland, Alex T.
Organic synthesis illustrating the effect of ring substituents on an aromatic ring.
Rowland, Alex T. J. Chem. Educ. 1995, 72, 548.
Mechanisms of Reactions |
Synthesis |
NMR Spectroscopy |
Aromatic Compounds
Synthesis of 1,1,1,3,3,3-Hexachloro-2,4-diisobutylcyclodiphosphaz(V)ane: An Inorganic Experiment  Tillman, Christopher; Wood, Gary L.; Hampton, Michael
Procedure for synthesizing a main group ring system.
Tillman, Christopher; Wood, Gary L.; Hampton, Michael J. Chem. Educ. 1995, 72, 547.
Synthesis
A New Investigative Laboratory for Introductory Organic Chemistry Involving Polymer Synthesis and Characterization  Kharas, Gregory B.
Project to develop a model organic laboratory curriculum that gives students the opportunity to be imaginative and creative by pursuing research projects in organic and polymer synthesis using a guided-discovery model.
Kharas, Gregory B. J. Chem. Educ. 1995, 72, 534.
Polymerization |
Synthesis
The Sassafras Tree and Designer Drugs: From Herbal Tea to Ecstasy  French, Larry G.
Using historical development of material from the sassafras tree and elicit synthesis of the drug ecstasy (MDMA) as a venue for presenting methodology for amine synthesis in organic chemistry.
French, Larry G. J. Chem. Educ. 1995, 72, 484.
Drugs / Pharmaceuticals |
Synthesis |
Enrichment / Review Materials |
Molecular Properties / Structure
Steric Hindrance by Bromination of Alkylbenzenes: Experimental Demonstration  Cooley, James H.; Abobaker, Nagib M.
Procedure to illustrate the influence of steric hindrance on organic chemistry in which students must decide what data to collect and how to interpret it.
Cooley, James H.; Abobaker, Nagib M. J. Chem. Educ. 1995, 72, 463.
Molecular Properties / Structure |
Synthesis |
Chirality / Optical Activity |
Aromatic Compounds |
Stereochemistry
Electrophilic Aromatic Substitution Discovery Lab  Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia
An organic chemistry lab for introductory chemistry in which students must determine the reaction mechanism of an organic synthesis; includes sample data and analysis.
Jarret, Ronald M.; New, Jamie; Patraitis, Cynthia J. Chem. Educ. 1995, 72, 457.
Synthesis |
Mechanisms of Reactions |
Electrophilic Substitution
Acetylation of Ferrocene: A Study of the Friedel-Crafts Acylation Mechanism as Measured by HPLC Using an Internal Standard  Newirth, Terry L.; Srouji, Nadine
An experimental procedure that allows students to reach conclusions about the mechanism of an organic reaction (Friedel-Crafts acylation) based on their own data analysis; includes sample data and analysis.
Newirth, Terry L.; Srouji, Nadine J. Chem. Educ. 1995, 72, 454.
Mechanisms of Reactions |
Synthesis |
Chromatography |
HPLC
3,9-Diaryl-2,4,8,10-Tetraoxaspiro[5.5]Undecanes by Rapid Microscale Preparation: Products with Instructive NMR Spectra  Clark, Thomas J.
Organic synthesis designed to produce product with an interesting structure to illustrate the effects of conformation and symmetry on NMR spectra; includes sample data and analysis.
Clark, Thomas J. J. Chem. Educ. 1995, 72, 375.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Synthesis |
Microscale Lab
Hammett Correlations of Amide Proton Chemical Shifts: An Organic or Spectroscopy Experiment  Setliff, F. L.; Soman, N. G.; Toland, A. D.
Experiment designed to illustrate the quantitative relationship between an easily measurable property (amide proton NMR chemical shift) and the electronic effect of several different substituents on substituted benzanilides; includes sample data and analysis.
Setliff, F. L.; Soman, N. G.; Toland, A. D. J. Chem. Educ. 1995, 72, 362.
Synthesis |
NMR Spectroscopy |
Molecular Properties / Structure |
Amides
Characterization of the Product from the Thermal Decomposition of Chromium (III) Nitrate and Urea: An Undergraduate Project Involving an Unknown Metal complex.  House, Donald A.; Searle, Graeme H.
Procedure requiring groups of students to determine the identity of an unknown metal complex produced by the thermal decomposition of urea in the presence of chromium(III) nitrate; includes data analysis.
House, Donald A.; Searle, Graeme H. J. Chem. Educ. 1995, 72, 360.
Metals |
Coordination Compounds |
Synthesis |
Qualitative Analysis
Baker's Yeast Reduction of alpha-Diketones: A Four-Hour Experiment for Undergraduate Students  Besse, Pascale; Bolte, Jean; Veschambre, Henri
Procedure for quickly and efficiently reducing alpha-diketones using bakers' yeast.
Besse, Pascale; Bolte, Jean; Veschambre, Henri J. Chem. Educ. 1995, 72, 277.
Oxidation / Reduction |
Synthesis |
Aldehydes / Ketones
Preparation of (S)-(+)-5,8a-Dimethyl-3,4,8,8a-tetrahydro-1,6(2H,7H)-naphthalenedione: An Undergraduate Experiment in Asymmetric Synthesis  Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E.
An asymmetric Robinson annelation suitable for the undergraduate organic laboratory.
Markgraf, J. Hodge; Fei, John F.; Ruckman, Robert E. J. Chem. Educ. 1995, 72, 270.
Synthesis |
Chirality / Optical Activity |
Aldehydes / Ketones
The Synthesis and Analysis of Copper (II) Carboxylates  Yoder, Claude H.; Smith, Wendy D.; Katolik, Vera L.; Hess, Kenneth R.; Thomsen, Marcus W.; Yoder, Carolyn S.; Bullock, Elizabeth R.
Several different methods for synthesizing and analyzing copper (II) carboxylates; includes sample data and analysis.
Yoder, Claude H.; Smith, Wendy D.; Katolik, Vera L.; Hess, Kenneth R.; Thomsen, Marcus W.; Yoder, Carolyn S.; Bullock, Elizabeth R. J. Chem. Educ. 1995, 72, 267.
Synthesis |
Laboratory Management
An Enhanced Chromatographic Technique for the Preparative Scale Purification of Acetyl Ferrocene  Davis, James; Vaughan, D. Huw; Cardosi Marco F.
Method and apparatus for producing and purifying significant amounts of acetyl ferrocene for laboratory analysis.
Davis, James; Vaughan, D. Huw; Cardosi Marco F. J. Chem. Educ. 1995, 72, 266.
Synthesis |
Laboratory Management |
Chromatography
Computer Simulation of Vinyl Polymer Tacticity  Radiotis, T.; Brown, G. R.
170. Statistical description of stereoregularity illustrated through the use of a computer program that uses Bernoullian statistics to simulate the relative handedness of successive monomer units along a polymer chain.
Radiotis, T.; Brown, G. R. J. Chem. Educ. 1995, 72, 133.
Synthesis |
Laboratory Computing / Interfacing |
Mathematics / Symbolic Mathematics |
Chemometrics
Solid-State Redox Chemistry: Preparation of 1,4-Naphthoquinone, Hydroquinone, and the Corresponding Mixed Quinhydrone in the Solid State  Morey, Jeroni; Frontera, Antoni
Procedure for synthesizing a mixed quinhydrone using solid-state methods.
Morey, Jeroni; Frontera, Antoni J. Chem. Educ. 1995, 72, 63.
Oxidation / Reduction |
Synthesis |
Solid State Chemistry
A Synthesis of 9-Fluorenol: Sodium Borohydride Reduction of 9-Fluorenone  Jones, C. Susana
Reduction of 9-fluorenone to generate 9-fluorenol.
Jones, C. Susana J. Chem. Educ. 1994, 71, A252.
Synthesis |
Aldehydes / Ketones |
Alcohols |
Microscale Lab
4-Bromo-2-Nitroaniline: A Multistep Synthesis  Elder, John W.; Paolillo, Marie A.
Multistep organic synthesis of 4-bromo-2-nitroaniline.
Elder, John W.; Paolillo, Marie A. J. Chem. Educ. 1994, 71, A144.
Microscale Lab |
Synthesis
The Modern Student Laboratory: Polyaniline-A Conducting Polymer: Electrochemical Synthesis and Electrochromic Properties  Sherman, Bradford Charles; Euler, William B.; Force, R. Ren
The construction, operation, and potential scope of application of a simple electrochemical cell that can be used to synthesize polyalanine and exhibit its electrochromic properties.
Sherman, Bradford Charles; Euler, William B.; Force, R. Ren J. Chem. Educ. 1994, 71, A94.
Electrochemistry |
Synthesis |
Electrolytic / Galvanic Cells / Potentials
Solid State Chemistry: Synthesis, Structures, and Properties of Selected Oxides and Sulfides (Wold, Aaron; Dwight, Kirby)  
Title of interest.
J. Chem. Educ. 1994, 71, A23.
Solid State Chemistry |
Synthesis
Chirotechnology: Industrial Synthesis of Optically Active Compounds (Sheldon, Roger A.)  
Title of interest.
J. Chem. Educ. 1994, 71, A23.
Synthesis |
Industrial Chemistry
Semimicroscale Organic Chemistry  Flash, Patrick; Phiri, Samuel; Mukherjee, Gita
Listing of 11 organic synthesis experiments converted to test tube scale to increase safety, decrease time and costs, and avoid the need for specialized glassware.
Flash, Patrick; Phiri, Samuel; Mukherjee, Gita J. Chem. Educ. 1994, 71, A5.
Microscale Lab |
Synthesis
Dinitration of 2-Benzylpyyridine: Microscale Synthesis of a Photochromic Compound  Gilfillan, Elizabeth D.; Pelter, Michael W.
Microscale synthesis of 2-[(2,4-dinitrophenyl)methyl]pyridine, which is tan in the absence of light but turns blue when exposed to light.
Gilfillan, Elizabeth D.; Pelter, Michael W. J. Chem. Educ. 1994, 71, A4.
Microscale Lab |
Synthesis |
Photochemistry |
Aromatic Compounds
Synthesis and Spectroscopic Study of Plant Growth Regulators Phenylpyridylureas: An "Agrorganic" Undergraduate Laboratory Experiment  Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette
This lab could represent an undergraduate comparative synthesis and analysis of biologically active molecules, suitable for an introductory lab session.
Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette J. Chem. Educ. 1994, 71, 1092.
Agricultural Chemistry |
Drugs / Pharmaceuticals |
Aldehydes / Ketones |
Aromatic Compounds |
Synthesis
An Advanced Inorganic Laboratory Experiment Using Synthesis and Reactivity of a Cycloheptatriene Molybdenum Complex  Timmers, Francis J.; Wacholtz, William F.
The reactions in the laboratory experiment described herein involve the synthesis, reactivity, and characterization of cycloheptatriene molybdenum.
Timmers, Francis J.; Wacholtz, William F. J. Chem. Educ. 1994, 71, 987.
Synthesis |
Organometallics |
Alkenes
Platinum(II) Chemistry Monitored by NMR Spectroscopy  Berry, David E.
Preparation and characterization of three platinum coordination compounds.
Berry, David E. J. Chem. Educ. 1994, 71, 899.
NMR Spectroscopy |
Synthesis |
Molecular Properties / Structure |
Coordination Compounds
Synthesis and Conformational Analysis of 1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose: A Nuclear Magnetic Resonance and Molecular Modeling Experiment  Midland, M. Mark; Beck, John J.; Peters, John L.; Rennels, Roger A.; Asirwatham, Gitanjali
Determining that the twist-boat conformation is favored in 1,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose.
Midland, M. Mark; Beck, John J.; Peters, John L.; Rennels, Roger A.; Asirwatham, Gitanjali J. Chem. Educ. 1994, 71, 897.
NMR Spectroscopy |
Molecular Modeling |
Carbohydrates |
Synthesis |
Conformational Analysis
The Preparation and Characterization of a Cellulose Xanthate Based Ion-Exchange Reagent  Wong, T. C.; Chan, W. H.; Cheng, V. K. W.
Converting the cellulose surface hydroxide group to the sodium salt of xanthate to serve as a low-cost ion-exchange material for the removal of heavy metals from waste effluents.
Wong, T. C.; Chan, W. H.; Cheng, V. K. W. J. Chem. Educ. 1994, 71, 803.
Ion Exchange |
Carbohydrates |
Synthesis
High-Temperature Synthesis of Anhydrous CrCl3 and the Thermally Controlled Formation of C6Cl6 and C2Cl6  Stevenson, Cynthia; Rudman, Reuben
Results of a systematic investigation of the synthesis of anhydrous chromium chloride and the various products produced under varying reaction conditions.
Stevenson, Cynthia; Rudman, Reuben J. Chem. Educ. 1994, 71, 704.
Synthesis |
Solid State Chemistry
Rare Earth Iron Garnets: Their Synthesis and Magnetic Properties  Geselbracht, Margaret J.; Cappellari, Ann M.; Ellis, Arthur B.; Rzeznik, Maria A.; Johnson, Brian J.
A general synthesis for compositions in the solid solution series YxGd3-xFe5O12 (x = 0, 1, 2, 3) and a simple demonstration that illustrates the differing magnetic properties of these materials.
Geselbracht, Margaret J.; Cappellari, Ann M.; Ellis, Arthur B.; Rzeznik, Maria A.; Johnson, Brian J. J. Chem. Educ. 1994, 71, 696.
Metals |
Transition Elements |
Magnetic Properties |
Synthesis |
Solid State Chemistry
Attracting the New Generation of Chemistry Majors to Synthetic Chemistry without Using Pheromones: A Research-Based, Group Approach to Multistep Syntheses at the College Sophomore Level  Amenta, Donna S.; Mosbo, John A.
An sophomore integrated inorganic/organic laboratory course whose focus is a group multistep synthetic problem based on departmental research efforts and including upper-level undergraduate chemistry students as peer mentors.
Amenta, Donna S.; Mosbo, John A. J. Chem. Educ. 1994, 71, 661.
Undergraduate Research |
Synthesis
The Hydration of 1-Hexene and 1-Hexyne  Touchette, Kim M.; Weiss, Hilton M.; Rozenberg, Daniel
The sulfuric acid-catalyzed hydration of 1-hexene and 1-hexyne.
Touchette, Kim M.; Weiss, Hilton M.; Rozenberg, Daniel J. Chem. Educ. 1994, 71, 534.
Alkynes |
Alkenes |
Alcohols |
Catalysis |
Synthesis
Polystyrene Kinetics by Infrared: An Experiment for Physical and Organic Chemistry Laboratories  Andrews-Henry, Heather
Procedure to determine the kinetics of the free radical polymerization of polystyrene.
Andrews-Henry, Heather J. Chem. Educ. 1994, 71, 357.
IR Spectroscopy |
Kinetics |
Polymerization |
Free Radicals |
Synthesis
Reliable and Economical Preparation of Macrocyclic Complexes: Synthesis and Reactivity of a Tetraazaligand for an Advanced Inorganic Laboratory  Chipperfield, John R.; Woodward, Simon
Preparation of Geodken's macrocycle.
Chipperfield, John R.; Woodward, Simon J. Chem. Educ. 1994, 71, 75.
Synthesis |
Coordination Compounds |
Transition Elements
Synthesis of metal halides   Grube, Karl; Leffler, Amos J.
Procedure for micro preparation of metal halides.
Grube, Karl; Leffler, Amos J. J. Chem. Educ. 1993, 70, A204.
Laboratory Equipment / Apparatus |
Metals |
Synthesis |
Microscale Lab
GC/MS experiments for the organic chemistry laboratory: I. E2 elimination of 2-bromo-2-methyloctane   Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott
Two capillary GC/MS experiments that were designed for and tested in a sophomore organic laboratory course.
Novak, Michael; Heinrich, Julie; Martin, Kristy A.; Green, John; Lytle, Scott J. Chem. Educ. 1993, 70, A103.
Gas Chromatography |
Alkenes |
Alkanes / Cycloalkanes |
Alcohols |
Elimination Reactions |
Synthesis
Robert Burns Woodward and the Art of Organic Synthesis (Bowden, Mary Ellen; Benfey, Theodor)  Kauffman, George B.
Review of a book designed as a teaching aid in high schools and colleges to accompany a traveling exhibit.
Kauffman, George B. J. Chem. Educ. 1993, 70, A52.
Synthesis
The aromatic substitution game  Zanger, Murray; Gennaro, Alfonso R.; McKee, James R.
This paper describes a game used to bring attention to the need for students to reconsider substitution theories learned in earlier chapters.
Zanger, Murray; Gennaro, Alfonso R.; McKee, James R. J. Chem. Educ. 1993, 70, 985.
Nucleophilic Substitution |
Synthesis
Determining Hammett sigma and rho values: Improvements on a published student experiment  Hathaway, Bruce A.; Olesen, Bjorn
Modifications and improvements to laboratory experiments written for an organic chemistry lab text.
Hathaway, Bruce A.; Olesen, Bjorn J. Chem. Educ. 1993, 70, 953.
Esters |
Acids / Bases |
Kinetics |
Synthesis
Photochemical and electrochemical studies of an organometallic sandwich compound: An inorganic chemistry experiment  Boyd, David C.; Johnson, Brian J.; Mann, Kent R.
Synthesis and study of the iron(II) sandwich compound [CpFe(tol)]PF6.
Boyd, David C.; Johnson, Brian J.; Mann, Kent R. J. Chem. Educ. 1992, 69, A315.
Photochemistry |
Electrochemistry |
Organometallics |
Synthesis
Preparation of 2,5-dimethyl-1-phenylpyrrole  Shaw, Dennis J.; Wood, William F.
Synthesis and characterization of 2,5-dimethyl-1-phenylpyrrole.
Shaw, Dennis J.; Wood, William F. J. Chem. Educ. 1992, 69, A313.
Heterocycles |
Synthesis |
Aromatic Compounds |
Microscale Lab
Microscale synthesis of azulene  Brieger, Gottfried
Procedure for the microscale synthesis of azulene.
Brieger, Gottfried J. Chem. Educ. 1992, 69, A262.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Alkenes |
Dyes / Pigments |
Mechanisms of Reactions
The synthesis of urea: An undergraduate laboratory experiment   Tanski, Stephanie; Petro, Janeen; Ball, David W.
This paper presents a laboratory experiment for the production of urea from silver cyanate and ammonium chloride.
Tanski, Stephanie; Petro, Janeen; Ball, David W. J. Chem. Educ. 1992, 69, A128.
Synthesis |
Reactions
Microscale synthesis of 2,6-bis(morpholinomethyl)-p-cresol: A phenolic Mannich base   Payne, Edward W.
This paper outlines a microscale laboratory preparation that is an extension of the basic Mannich reaction.
Payne, Edward W. J. Chem. Educ. 1992, 69, A40.
Microscale Lab |
Phenols |
Synthesis
Preparing and purifying 2,4-dinitrophenylhydrazones: Alternatives to the Brady procedure  Zhang, Juan; Hertzler, Russell L.; Eisenbraun, E. J.
Problems with and an alternative to the Brady procedure for preparing 2,4-dinitrophenylhydrazone; using a sulfonic acid ion-exchange resin in refluxing toluene.
Zhang, Juan; Hertzler, Russell L.; Eisenbraun, E. J. J. Chem. Educ. 1992, 69, 1037.
Synthesis |
Catalysis |
Aldehydes / Ketones
Synthesis and solvolysis of ferrocenylmethyl acetate: A multistep synthesis and kinetics experiment  Pinhas, Allan R.; Kevill, Dennis N.; D'Souza, Malcolm J.
A series of experiments that exposes students to the synthesis of ferrocenylmethyl acetate, different methods for monitoring a reaction, and the analysis of kinetic data.
Pinhas, Allan R.; Kevill, Dennis N.; D'Souza, Malcolm J. J. Chem. Educ. 1992, 69, 1034.
Synthesis |
Kinetics
Synthesis of epoxidated chalcone derivatives: A useful introductory undergraduate experiment in organic synthesis  Dixon, Christine E.; Pyne, Stephen G.
Modifications to a previously reported organic synthesis.
Dixon, Christine E.; Pyne, Stephen G. J. Chem. Educ. 1992, 69, 1032.
Synthesis |
Aromatic Compounds
Synthesis of a heteropolytungstate and its use in outer-sphere redox kinetics  Walmsley, Frank
An inorganic chemistry experiment has been developed combining two topics usually included in inorganic chemistry: heteropoly ions and mechanisms of oxidation-reduction reactions of transition metal ions.
Walmsley, Frank J. Chem. Educ. 1992, 69, 936.
Oxidation / Reduction |
Kinetics |
Synthesis |
Coordination Compounds
New recrystallization solvent for synthesis of a bicyclo[2.2.1]heptene  Harrison, Ernest A., Jr.
Toluene/hexane shown to be superior to EtOAc/MeOH as recrystallization solvent.
Harrison, Ernest A., Jr. J. Chem. Educ. 1992, 69, 860.
Synthesis |
Alkenes |
Solutions / Solvents |
Laboratory Management
Mass spectra of multi-halogen compounds: A student practical project  Holdsworth, David; Ching, Goh Siah; Hamid, Mohd Jamil bin Hj Abd
Synthesis of bromochloro analogues of DDT and examination of the products by gas chromatography-mass spectroscopy.
Holdsworth, David; Ching, Goh Siah; Hamid, Mohd Jamil bin Hj Abd J. Chem. Educ. 1992, 69, 856.
Mass Spectrometry |
Gas Chromatography |
Synthesis |
Reactions |
Mechanisms of Reactions
Synthesis of 5,6-dimethoxybenzofuroxan: An organic chemistry laboratory experiment  Eswaran, S. V.; Sajadian, S. K.
Synthesis and characterization of 5,6-dimethoxybenzofuroxan.
Eswaran, S. V.; Sajadian, S. K. J. Chem. Educ. 1992, 69, 839.
Synthesis |
Aromatic Compounds
Preparation of sucrose octaacetate-A bitter-tasting compound.  Mann, Thierry D.; Mosher, James D.; Wood, William F.
Acetylation of the eight hydroxy groups of sucrose changes its sweet taste to intensely bitter.
Mann, Thierry D.; Mosher, James D.; Wood, William F. J. Chem. Educ. 1992, 69, 668.
Synthesis |
Carbohydrates |
Catalysis
C60 and C70 made simply.  Craig, Norman C.; Gee, Gilbert C.; Johnson, Adam R.
Procedure and apparatus for synthesizing C60 and C70.
Craig, Norman C.; Gee, Gilbert C.; Johnson, Adam R. J. Chem. Educ. 1992, 69, 664.
Laboratory Equipment / Apparatus |
Synthesis |
Alkenes
Simple generation of C60 (Buckminsterfullerene).  Iacoe, David A.; Potter, William T.; Teeters, Dale.
A simple means for the production of fullerene-enhanced graphitic soot using equipment commonly found in most undergraduate chemistry and physics laboratories.
Iacoe, David A.; Potter, William T.; Teeters, Dale. J. Chem. Educ. 1992, 69, 663.
Synthesis |
Laboratory Equipment / Apparatus |
Alkenes
Synthesis and reactions of benzofurazan-1-oxide.  Terrian, Deborah L.; Houghtaling, Melissa A.; Ames, James R.
An elementary experiment that can be used to familiarize students with the synthesis and reactions of nitrogen heterocycles.
Terrian, Deborah L.; Houghtaling, Melissa A.; Ames, James R. J. Chem. Educ. 1992, 69, 589.
Synthesis |
Heterocycles |
Aromatic Compounds
Corn chip aroma: A classroom demonstration on the preparation of a Schiff base  Sartori, Antony T.; Wood, William F.
Preparing 3-methylimino-2-butanone.
Sartori, Antony T.; Wood, William F. J. Chem. Educ. 1992, 69, 572.
Aldehydes / Ketones |
Synthesis |
Reactions |
Mechanisms of Reactions
The importance of temperature control in the preparation of phencyclone (1,3-diphenyl-2-H-cyclopenta[I]phenanthrene-2-one).  Harrison, Ernest A., Jr.
The addition of a methanolic alkali solution to the reactant mixture increases yields to 80%.
Harrison, Ernest A., Jr. J. Chem. Educ. 1992, 69, 571.
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
Organic synthesis by relay.  Crute, Thomas D.
Teams of organic students race one another at the chalkboard to devise plausible organic syntheses.
Crute, Thomas D. J. Chem. Educ. 1992, 69, 559.
Synthesis |
Enrichment / Review Materials
Diamminedichloroplatinum(II) (the author replies).  Singh, Mono M.
Acknowledges an earlier macroscale synthesis.
Singh, Mono M. J. Chem. Educ. 1992, 69, 516.
Synthesis
Diamminedichloroplatinum(II).  Kauffman, George B.
Failure to cite an earlier macroscale synthesis.
Kauffman, George B. J. Chem. Educ. 1992, 69, 516.
Synthesis
A synthesis of indane musk Celestolide  Kagabu, Shinzo; Kojima, Yuka
This convenient operation using only a calculated amount of tetrahydrofuran will help students understand that one of the real operative species in Grignard reaction is a complex of alkylmagnesium halogenide with ether molecules.
Kagabu, Shinzo; Kojima, Yuka J. Chem. Educ. 1992, 69, 420.
Synthesis |
Grignard Reagents
Teaching organic synthesis: An advanced organic chemistry course that uses the primary literature  French, Larry G.
An overview is presented of an advanced organic synthesis course developed over the past several years that uses primary literature sources in lieu of a text.
French, Larry G. J. Chem. Educ. 1992, 69, 287.
Synthesis
A new method for the oxidation of 4-phenylurazole to 4-phenyltriazolinedione.  Mallakpour, Shadpour E.
The procedures describe the synthesis of 4-phenyl-urazole from ethyl carbazate and then the oxidation of the urazole with NO2-N2O4 to yield 4-phenyl-1,2,4-trizoline-3,5-dione.
Mallakpour, Shadpour E. J. Chem. Educ. 1992, 69, 238.
Oxidation / Reduction |
Aldehydes / Ketones |
Synthesis |
Aromatic Compounds
Higher order cycloaddition reactions of adamantyl isobenzofulvene and isobenzofuran: A microscale synthesis illustrating the involvement of highly reactive intermediates and a simple FMO treatment of their cycloaddition periselectivities  Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N.
The authors have developed an undergraduate laboratory experiment to illustrate a cycloaddition reaction using a simple mathematical approach.
Russell, Richard A.; Longmore, Robert W.; Warrener, Ronald N. J. Chem. Educ. 1992, 69, 164.
Microscale Lab |
Alkenes |
Synthesis |
MO Theory
A serendipitous two-step synthesis from a Grignard reaction: 1-ethoxy-1,1,1-triphenlymethane from the reaction of phenylmagnesium bromide with benzophenone  Abhyankar, Sudhir B.; Dust, Julian M.
To illustrate the potential products of a Grignard reaction, students prepared phenylmagnesium bromide from bromobenzene and magnesium turnings in diethyl ether. The Grignard reagent was then allowed to react with benzophenone.
Abhyankar, Sudhir B.; Dust, Julian M. J. Chem. Educ. 1992, 69, 76.
Synthesis |
Grignard Reagents
Beta-keto esters from tin(II) chloride catalyzed reactions of aldehydes with ethyl diazoacetate: An undergraduate laboratory experiment drawn from the current literature  Brockwell, Joyce C.; Holmquist, Christopher R.
This is an experimental procedure for producing longer-chain keto esters from unconjugated aldehydes on reaction with ethyl diazoacetate catalyzed by Lewis acids for use in an undergraduate laboratory.
Brockwell, Joyce C.; Holmquist, Christopher R. J. Chem. Educ. 1992, 69, 68.
Catalysis |
Synthesis |
Lewis Acids / Bases |
Aldehydes / Ketones |
Esters
Synthesis of trans-2-tert-butylcyclohexanol via hydroboration: A microscale organic experiment demonstrating syn addition  Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P.
This microscale experiment demonstrates the relative stereochemistry of the titled addition.
Wigal, Carl T.; Hopkins, William T.; Ronald, Bruce P. J. Chem. Educ. 1991, 68, A299.
Synthesis |
Microscale Lab |
Addition Reactions |
Aromatic Compounds |
Stereochemistry
The Wittig synthesis of alkenes by phase-transfer catalysis: The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene   Breuer, Stephen W.
The syntheses of 4,4'-dichlorostilbenes and of E, E-1,4 -diphenylbutadiene.
Breuer, Stephen W. J. Chem. Educ. 1991, 68, A58.
Synthesis |
Microscale Lab |
Alkenes |
Aromatic Compounds
A safe and novel polymerization of styrene   Flynn, Brendan R.
A safer way to demonstrate the synthesis of addition polymers.
Flynn, Brendan R. J. Chem. Educ. 1991, 68, 1038.
Polymerization |
Synthesis |
Consumer Chemistry
Direct electrochemical synthesis of fluoroiron compounds: The use of sacrificial metal anodes in aqueous medium  Chakravorti,M.C.; Subrahamanyam, Gampa V.B.
The direct electrochemical synthesis of fluoro iron compounds can be used to show students how metal compounds can be prepared from the pure metal itself and how fluoro compounds can be prepared with relative ease from diluted aqueous hydrofluoric acid solutions.
Chakravorti,M.C.; Subrahamanyam, Gampa V.B. J. Chem. Educ. 1991, 68, 961.
Electrochemistry |
Oxidation / Reduction |
Acids / Bases |
Synthesis
Attaining optimal conditions: An advanced undergraduate experiment that introduces experimental design and optimization  Van Ryswyk, Hal; Van Hecke, Gerald R.
The experiment described is a five-period exercise in experimental design and optimization performed in a junior laboratory course that integrates synthesis and analysis.
Van Ryswyk, Hal; Van Hecke, Gerald R. J. Chem. Educ. 1991, 68, 878.
Undergraduate Research |
Synthesis |
Chromatography
The synthesis of some deazenido and hydrazido complexes of molybdenum  Dilworth, J. R.; Miller, J. R.
In this series of experiments, the authors report the synthesis of some complexes that containing nitrogenous ligands with readily available sulfur donors. Such reactions are currently of interest as researchers study nitrogen fixation.
Dilworth, J. R.; Miller, J. R. J. Chem. Educ. 1991, 68, 788.
IR Spectroscopy |
Synthesis
Synthetic applications of aromatic metabolites  Armstead, D. E. F.
A sequel lab to clove oil extraction.
Armstead, D. E. F. J. Chem. Educ. 1991, 68, 698.
Aromatic Compounds |
Alcohols |
Natural Products |
Synthesis
The three-step synthesis of 2,6-dinitro-4-methylaniline from p-toluidine  Todd, David
A multistep synthesis for the beginning organic chemistry lab.
Todd, David J. Chem. Educ. 1991, 68, 682.
Synthesis |
Aromatic Compounds |
Amides
Synthesis and characterization of dinuclear tungsten carbonyl anions  McNeese, Timothy J.
The purpose of the synthesis and characterization of the compounds discussed here is to introduce upper level inorganic chemistry students to certain fundamental principles and laboratory techniques of organometallic chemistry.
McNeese, Timothy J. J. Chem. Educ. 1991, 68, 678.
Organometallics |
Synthesis |
NMR Spectroscopy
A laboratory study of 1,3-dipole-dipolarophile addition: An extension of the Diels Alder reaction  Gingrich, Henry L.; Pickering, Miles
Some easy organic reactions that can also be used as the basis for puzzles, or as facile heterocyclic syntheses: an area neglected in the student experiment literature.
Gingrich, Henry L.; Pickering, Miles J. Chem. Educ. 1991, 68, 614.
Mechanisms of Reactions |
Addition Reactions |
Synthesis |
Heterocycles |
Physical Properties |
NMR Spectroscopy
A facile semisynthesis of the antimalarial drug Qinghaosu  Roth, Ronald J.; Acton, Nancy
Semisynthesis of the antimalarial drug.
Roth, Ronald J.; Acton, Nancy J. Chem. Educ. 1991, 68, 612.
Synthesis |
Drugs / Pharmaceuticals |
Medicinal Chemistry
Diastereospecific synthesis of cis- and trans-2,3-dimethyl-1,4-thiamorpholines  Gallego, Maria Teresa; Brunet, Ernesto; Garcia Ruano, Jose Luis; Eliel, Ernest L.
A multistep, diastereospecific synthesis of cis and trans-2,3,dimethyl-1,4-thiamorpholines that the authors have used as a laboratory exercise for advanced undergraduate students.
Gallego, Maria Teresa; Brunet, Ernesto; Garcia Ruano, Jose Luis; Eliel, Ernest L. J. Chem. Educ. 1991, 68, 517.
Diastereomers |
NMR Spectroscopy |
Synthesis
Organic electrosynthesis without a potentiostat: Selectivity in the stepwise reduction of trichloromethylphosphonate: A representative experiment  Le Menn, Jean-Christophe; Tallec, Andre; Sarrazin, Jean
In this paper, authors propose two short experiments that illustrate a means of performing easily and selectively the stepwise reduction of a polyhaplophosphonate in aqueous media.
Le Menn, Jean-Christophe; Tallec, Andre; Sarrazin, Jean J. Chem. Educ. 1991, 68, 513.
Acids / Bases |
Alkylation |
Electrochemistry |
Electrolytic / Galvanic Cells / Potentials |
Synthesis |
Potentiometry
Demonstrating organic synthesis with familiar materials   Rothenberger, Otis; Bunting, Roger; Newton, Thomas
Two chemical synthesis demonstrations for elementary, high school, college, and adult audiences.
Rothenberger, Otis; Bunting, Roger; Newton, Thomas J. Chem. Educ. 1991, 68, 502.
Synthesis |
Esters |
Natural Products
Vinyl chloride in Asia   King, Roy H.; Reuben, Bryan G.
A case study of a consulting visit by one of the authors to an Asian country.
King, Roy H.; Reuben, Bryan G. J. Chem. Educ. 1991, 68, 480.
Industrial Chemistry |
Polymerization |
Synthesis
Photochromic sunglasses: A patent-based advanced organic synthesis project and demonstration  Osterby, Bruce; McKelvey, Ronald D.; Hill, Lisa
An ideal individual project for an upper level student: interesting chemistry, relevant applications, and effective demonstrations.
Osterby, Bruce; McKelvey, Ronald D.; Hill, Lisa J. Chem. Educ. 1991, 68, 424.
Applications of Chemistry |
Photochemistry |
Synthesis
And the structure is ... ?  Stradling, S. S.
An experiment for advanced organic lab students which challenges a student's ingenuity as a determiner of structure.
Stradling, S. S. J. Chem. Educ. 1991, 68, 378.
Grignard Reagents |
Qualitative Analysis |
Synthesis
Axial ligand effects on the spin state and electrochemistry of iron porphyrins: An advanced laboratory experiment  Geiger, David K.
An advanced laboratory experiment involving synthesis and characterization of iron porphyrins.
Geiger, David K. J. Chem. Educ. 1991, 68, 340.
Coordination Compounds |
Magnetic Properties |
Electrochemistry |
Synthesis
A convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety  Price, William A.; Patten, Timothy E.
Description of a convenient synthesis of 3,4-pentadien-1-ol from 3-butyn-1-ol: Spectral analysis and unusual durability of the allene moiety.
Price, William A.; Patten, Timothy E. J. Chem. Educ. 1991, 68, 256.
Synthesis |
Alcohols |
Alkenes |
NMR Spectroscopy
The synthesis of 2'-bromostyrene  Corvari, Linda; McKee, James R.; Zanger, Murray
Organic chemistry laboratories need not be the repositories of foul smells. This synthesis produces an aroma akin to hyacinth.
Corvari, Linda; McKee, James R.; Zanger, Murray J. Chem. Educ. 1991, 68, 161.
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Stereochemistry |
Alkenes
The synthesis of 2-methyl-4-heptanone  de Jong, Elma A.; Feringa, Ben L.
2-methyl-4-heptanone is an ant pheromone used to alarm fellow ants. The synthesis described in this article is greeted with interest by students.
de Jong, Elma A.; Feringa, Ben L. J. Chem. Educ. 1991, 68, 71.
Aldehydes / Ketones |
Natural Products |
Synthesis |
Grignard Reagents
Fabric softeners as phase transfer catalyst in organic synthesis  Lee, Albert W. M.; Yip, W. C.
Phase transfer catalysts such as quaternary ammonium compounds are often found in commercial fabric softeners due to their antistatic properties.
Lee, Albert W. M.; Yip, W. C. J. Chem. Educ. 1991, 68, 69.
Gas Chromatography |
NMR Spectroscopy |
Catalysis |
Synthesis
Benzoylacetic acid: Synthesis and examination of the tautomeric equilibrium  Rosenfeld, Stuart; William, Alecia
A lab sequence that includes challenging techniques appropriate for advanced undergraduates involving synthesis and physical organic chemistry. With supplemental work, this lab simulates the full range of operation of a professional chemist.
Rosenfeld, Stuart; William, Alecia J. Chem. Educ. 1991, 68, 66.
Synthesis |
Spectroscopy |
NMR Spectroscopy |
Equilibrium |
IR Spectroscopy
Biocatalysis in organic solvents  Natarajan, K. R.
This article highlights why it is sometimes desirable to select organic solvents when carrying out enzymatic reactions, criteria for solvent selection, effects of organic solvents on enzymes, applications, and future prospects.
Natarajan, K. R. J. Chem. Educ. 1991, 68, 13.
Bioorganic Chemistry |
Synthesis |
Solutions / Solvents |
Catalysis |
Enantiomers |
Enzymes
The microscale synthesis and purification of N, N-diethyl-m-toluamide (Deet): An experiment for a project-oriented organic chemistry course  LeFevre, Joseph W.
Procedure for the microscale synthesis and purification of N, N-diethyl-m-toluamide (Deet).
LeFevre, Joseph W. J. Chem. Educ. 1990, 67, A278.
Microscale Lab |
Synthesis |
Aromatic Compounds
Microscale synthesis of cis-diamminedihaloplatinum(II) and a corresponding trans isomer: A rapid and convenient method of preparing cisplatin - An anticancer drug. A laboratory experiment for inorganic and bioinorganic chemistry  Singh, Mono M.; Szafran, Zvi; Pike, Ronald M.
Involves drug synthesis, application of the trans effect, and preparation and characterization of isomers under different reaction conditions.
Singh, Mono M.; Szafran, Zvi; Pike, Ronald M. J. Chem. Educ. 1990, 67, A261.
Microscale Lab |
Synthesis |
Drugs / Pharmaceuticals |
Bioinorganic Chemistry |
Diastereomers
Synthesis of iodohexane via hydroboration-iodination: A microscale organic laboratory experiment involving air-sensitive compounds  Gooch, E. Eugene
Use of ICl and organoborane intermediates to prepare iodohexane that parallels similar methods that introduce iodine radionuclides into fatty acids for use as heart imaging agents via positron emission tomography.
Gooch, E. Eugene J. Chem. Educ. 1990, 67, A232.
Synthesis |
Microscale Lab |
Carboxylic Acids |
Medicinal Chemistry
Microscale synthesis of trans-chlorocarbonylbis(triphenylphosphine)rhodium(I) and its reactions: A versatile metal carbonyl complex: An intermediate- or advanced-level inorganic chemistry experiment  Singh, Mono M.; Szafran, Zvi; Pike, Ronald M.
An alternative route to the synthesis of carbonyl compounds in which the safer N, N - dimethylformamide is employed as the source of the carbonyl group.
Singh, Mono M.; Szafran, Zvi; Pike, Ronald M. J. Chem. Educ. 1990, 67, A180.
Synthesis |
Coordination Compounds
Development of an advanced synthesis laboratory course in Nobel Prize winning chemistry  Doxsee, Kenneth M.
The study through lecture and laboratory investigations the work of those chemists who were ultimately awarded the Nobel Prize; includes course organization, content, and a description of the laboratory component.
Doxsee, Kenneth M. J. Chem. Educ. 1990, 67, 1057.
Synthesis
Preparation of 1-phenyl-3-phenylaminopyrrolidine-2,5-dione: An organic laboratory experiment on the Michael addition  Ram, Ram N.; Varsha, Kiran
Acylation of aniline with maleic anhydride to give maleanilic acid followed by Michael addition of aniline and cyclization to yield 1-phenyl-3-phenylaminopyrrolidine-2,5-dione.
Ram, Ram N.; Varsha, Kiran J. Chem. Educ. 1990, 67, 985.
Addition Reactions |
Aldehydes / Ketones |
Synthesis
Synthesis of a phenol-formaldehyde thermosetting polymer  Bedard, Y.; Riedl, B.
Procedure that allows for the synthesis of a 50% aqueous solution of a prepolymer that, with the proper application of heat and pressure, can be used to bind together wood or other materials.
Bedard, Y.; Riedl, B. J. Chem. Educ. 1990, 67, 977.
Synthesis |
Aldehydes / Ketones |
Phenols |
Polymerization
An operationally simple hydroboration-oxidation experiment  Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana
The reactions involve the use of in situ generated diborane as the hydroborating reagent and sodium perborate as the oxidizing agent to convert cyclopentene to cyclopentanol.
Kabalka, George W.; Wadgaonkar, Prakash P.; Chatla, Narayana J. Chem. Educ. 1990, 67, 975.
Synthesis |
Mechanisms of Reactions |
Alkenes |
Alcohols
A simple and convenient method to prepare hydrogen chloride gas  Maurya, Mannar R.
A simple and convenient method for preparing HCl gas from common materials (sulfuric and hydrochloric acids) without producing any waste.
Maurya, Mannar R. J. Chem. Educ. 1990, 67, 974.
Synthesis |
Laboratory Management
Disconnect by the numbers: A beginner's guide to synthesis  Smith, Michael B.
A protocol for planning organic syntheses using the disconnection method.
Smith, Michael B. J. Chem. Educ. 1990, 67, 848.
Synthesis |
Mechanisms of Reactions
Gravimetric analysis: The synthesis of tin iodide  Hickling, George G.
Preparation of tin(IV) iodide to further students' understanding of quantitative analysis and introduce some new laboratory techniques.
Hickling, George G. J. Chem. Educ. 1990, 67, 702.
Gravimetric Analysis |
Synthesis |
Quantitative Analysis
Industrial chemistry in the organic laboratory: C4 alkylations  Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D.
A set of experiments to illustrate reactions of the tertiary-butyl group; the products are all compounds that occur in consumer products and have received considerable attention in the popular press (BHT, BHA, TBHQ, and MTBE).
Teegarden, David M.; Varco-Shea, Theresa C.; Conklin, Karen T.; Markle, Cynthia A.; Anderson, Scott D. J. Chem. Educ. 1990, 67, 619.
Industrial Chemistry |
Aromatic Compounds |
Phenols |
Synthesis |
Mechanisms of Reactions
Synthesis of 3-(2'-methoxy,5'-bromophenyl)-2,3-epoxy phenyl propanone, A novel epoxidated chalcone derivative: An undergraduate organic chemistry experiment  Moloney, Gerard P.
Synthesis of 3-(2'-methoxy,5'-bromophenyl)-1-phenyl-prop-2-enone and its subsequent epoxidation to 3-(2'-methoxy,5'- bromophenyl)-2,3-epoxy phenyl propanone.
Moloney, Gerard P. J. Chem. Educ. 1990, 67, 617.
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones |
Ethers |
Mechanisms of Reactions
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment  Stranberg, Michael; Anselme, J. -P.
A simple procedure for the base-catalyzed cleavage of benzopinacolone to triphenylmethane: An undergraduate experiment.
Stranberg, Michael; Anselme, J. -P. J. Chem. Educ. 1990, 67, 616.
Catalysis |
Aldehydes / Ketones |
Mechanisms of Reactions |
Synthesis
The preparation of pure zeolite NaY and its conversion to high-silica faujasite: An experiment for laboratory courses in inorganic chemistry  Blatter, Fritz; Schumacher, Ernst
The authors give a simple, reproducible method for the preparation of zeolite NaY from analytically pure chemicals.
Blatter, Fritz; Schumacher, Ernst J. Chem. Educ. 1990, 67, 519.
Crystals / Crystallography |
Synthesis
Carbon-11: Where familiar chemistry still holds new challenges  Feliu, Anthony L.
Organic synthesis for biomedical applications with carbon-11 is made feasible by the high activities which can be cyclotron produced compared to the quantity required for a patient study.
Feliu, Anthony L. J. Chem. Educ. 1990, 67, 364.
Isotopes |
Synthesis
Preparation, analysis, and reactivity of bis[N,N-bis(trimethylsilyl)amino]tin(II): An advanced undergraduate laboratory project in organometallic synthesis  Schaeffer, Charles D., Jr.; Myers, Lori K.; Coley, Suzanne M.; Otter, Julie C.; Yoder, Claude H.
As a part of the authors continuing series on advanced undergraduate laboratory projects involving synthesis and multimuclear NMR spectroscopy, they offer a project that explores the preparation and analysis of tin(II) amine.
Schaeffer, Charles D., Jr.; Myers, Lori K.; Coley, Suzanne M.; Otter, Julie C.; Yoder, Claude H. J. Chem. Educ. 1990, 67, 347.
Organometallics |
Synthesis |
NMR Spectroscopy |
Amines / Ammonium Compounds
Elementary quantitative inorganic analysis: A strategy and some experiments  Blayden, H. E.; Jones, P. J.; Webster, M.
A brief description of an undergraduate course in practical inorganic chemistry is described as well as the syntheses and outline of three of the compounds currently used.
Blayden, H. E.; Jones, P. J.; Webster, M. J. Chem. Educ. 1990, 67, 342.
Quantitative Analysis |
Synthesis
From cyclohexanol to diethyl hexanedioate (diethyl adipate): A two-step synthetic sequence for microscale organic laboratory   Wintner, Claude E.; Gray, Christina A.
The authors have developed a two-step microscale sequence from cyclohexanol through adipic acid to diethyl adipate that has proved to be successful in the first year organic laboratory.
Wintner, Claude E.; Gray, Christina A. J. Chem. Educ. 1990, 67, 341.
Microscale Lab |
Synthesis |
Alcohols
The palladium-catalyzed oxidation of 2-vinylnaphthalene: A microscale organic synthesis experiment   Byers, Jeffrey H.; Ashfaq, Aalla; Morse, Wendy R.
The Wacker oxidation experiment as described is cost-efficient due to the small scale employed, and is a valuable addition to the undergraduate organic curriculum.
Byers, Jeffrey H.; Ashfaq, Aalla; Morse, Wendy R. J. Chem. Educ. 1990, 67, 340.
Microscale Lab |
Synthesis |
Alkynes |
Aldehydes / Ketones |
Oxidation / Reduction
Microscale synthesis of heterocyclic compounds   Al-awar, Rima; Wahl, George H., Jr.
The authors describe microscale syntheses of four heterocyclic compounds for which large-scale versions were described previously in this Journal.
Al-awar, Rima; Wahl, George H., Jr. J. Chem. Educ. 1990, 67, 265.
Microscale Lab |
Heterocycles |
Esters |
Aromatic Compounds |
Synthesis
Synthesis of an enkephalinase inhibitor, Gly-Gly-Phe-Leu, by continuous-flow peptide synthesizer  Iskander, Magdy N.; Jones, Paul A.
The assembly of the continuous flow peptide synthesizer was carried out in the author's laboratory with no difficulty and has generated great interest among their students.
Iskander, Magdy N.; Jones, Paul A. J. Chem. Educ. 1990, 67, 170.
Synthesis |
Proteins / Peptides |
Medicinal Chemistry |
Laboratory Equipment / Apparatus
The nitration of phenacetin: A structured project approach to teaching organic chemistry in undergraduate laboratory classes  Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W.; Dutton, B. Hoang; Harland, Lesley
In this program students complete a basic synthesis and then initiate a related pseudo-research program that progressively challenges their experimental skills and their capacity to think as practicing organic chemists.
Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W.; Dutton, B. Hoang; Harland, Lesley J. Chem. Educ. 1990, 67, 168.
Synthesis
The synthesis of substituted benzyl phenyl ethers: An undergraduate organic chemistry experiment  Dilts, Kimberly; Durand, Marc
The experiment presented here presents a convenient and safe procedure for the semimicro SN2 Williamson synthesis of benzyl phenyl ethers.
Dilts, Kimberly; Durand, Marc J. Chem. Educ. 1990, 67, 74.
Synthesis |
Ethers |
Titration / Volumetric Analysis
The preparation of Indanthrene Scarlet GG: A vat dye experiment for the introductory organic chemistry laboratory  Lutz, Wilson B.
The vat dye Indanthrene Scarlet GG can easily be synthesized and applied to cloth within a single two hour laboratory period.
Lutz, Wilson B. J. Chem. Educ. 1990, 67, 71.
Synthesis |
Dyes / Pigments |
Alkenes
g-Nonanoic lactone: Synthesis of a fragrance and flavor enhancer in the undergraduate laboratory  Bunce, Richard A.; Reeves, Henry D.
The experiment describes the synthesis of ?-nonanoic lactone, an un-natural compound having the odor and flavor of coconuts.
Bunce, Richard A.; Reeves, Henry D. J. Chem. Educ. 1990, 67, 69.
Synthesis |
Aldehydes / Ketones
The stepwise nitration of toluene: A multistep microscale synthesis based on an industrial process  Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W.
The stepwise synthesis of 2,4,6-trinitrotoluene is a simple but important industrial example of electrophilic aromatic substitution that reflects a decreasing reactivity accompanying the increasing degree of nitration.
Russell, Richard A.; Switzer, Robert W.; Longmore, Robert W. J. Chem. Educ. 1990, 67, 68.
Microscale Lab |
Industrial Chemistry |
Aromatic Compounds |
Synthesis |
HPLC
A derivation of the Masamune rule of multiplicativity in double asymmetric induction  Nakayama, Kensaku
The ability to prepare one diastereomeric or enantiomeric isomer in excess in a given chemical transformation where a stereoisomeric distribution of products is possible is currently one of the most highly sought goals in the field of synthetic organic chemistry.
Nakayama, Kensaku J. Chem. Educ. 1990, 67, 20.
Synthesis |
Diastereomers |
Enantiomers
The resolution of a completely inorganic coordination compound: A modified classic experiment for the inorganic laboratory  Yasui, Takaji; Ama, Tomoharu; Kauffman, George B.
Reproducing Alfred Werner's experiment demonstrating the Co(III) possesses an octahedral configuration.
Yasui, Takaji; Ama, Tomoharu; Kauffman, George B. J. Chem. Educ. 1989, 66, 1045.
Coordination Compounds |
Synthesis |
Diastereomers
Coordination complexes of cobalt: Inorganic synthesis in the general chemistry laboratory  Williams, Gregory M.; Olmstead, John, III; Breksa, Andrew P., III
An experiment involving synthesis and spectral studies of a series of [Co(NH3)5L] complexes that introduces general chemistry students to inorganic synthesis and allows them to conduct a systematic study on the effect of different ligands on absorption spectra.
Williams, Gregory M.; Olmstead, John, III; Breksa, Andrew P., III J. Chem. Educ. 1989, 66, 1043.
Coordination Compounds |
Synthesis |
Spectroscopy
The space group of cis-bis(ethylenediamine)bis(azido)cobalt(III) nitrate: An undergraduate physical inorganic experiment  Cooper, J. N.; Smith, D. A.; Kastner, M. E.
The synthesis and precession photography of cis-bis(ethylenediamine)bis(azido)cobalt(III) nitrate.
Cooper, J. N.; Smith, D. A.; Kastner, M. E. J. Chem. Educ. 1989, 66, 968.
Crystals / Crystallography |
Synthesis
Microscale synthesis and analysis of a dipeptide  Blatchly, Richard A.; Allen, Timothy R.; Bergstrom, Dirk T.; Shinozaki, Yuji
The synthesis of a dipeptide from its component amino acids and its analysis by chiral-phase thin-layer chromatography.
Blatchly, Richard A.; Allen, Timothy R.; Bergstrom, Dirk T.; Shinozaki, Yuji J. Chem. Educ. 1989, 66, 965.
Microscale Lab |
Synthesis |
Proteins / Peptides |
Thin Layer Chromatography |
Amino Acids
A simple synthesis  Bindel, Thomas H.
Procedure to introduce students to flame and silver nitrate qualitative analysis, and then apply these techniques to identify the product of a synthesis.
Bindel, Thomas H. J. Chem. Educ. 1989, 66, 847.
Synthesis |
Qualitative Analysis
Evolution of the morphinan synthesis  Lednicer, Daniel
The key reaction to the preparation of morphinans is the Grewe carbocation cyclization.
Lednicer, Daniel J. Chem. Educ. 1989, 66, 718.
Synthesis |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Mechanisms of Reactions |
Aromatic Compounds
The bismuth-sodium nitrate reaction  Hill, William D., Jr.
Reaction for preparing bismuth(III) oxide and determining its percentage yield.
Hill, William D., Jr. J. Chem. Educ. 1989, 66, 709.
Reactions |
Synthesis
Synthesis and uses of ammonia: A unified approach to problem solving in physical chemistry  Jordan, A. D.; Birss, F. W.; Fraga, S.
A collection of 59 physical chemistry problems regarding the synthesis of ammonia are available from the author.
Jordan, A. D.; Birss, F. W.; Fraga, S. J. Chem. Educ. 1989, 66, 694.
Synthesis
Tetraxaquaterene syntheses  Norkjaer, Kim; Senning, Alexander
The synthesis of tetraxaquaterene does not illustrate the "template effect".
Norkjaer, Kim; Senning, Alexander J. Chem. Educ. 1989, 66, 672.
Synthesis
Getting away from the cookbook in the organic laboratory  Potter, Neil H.; McGrath, Thomas F.
An organic laboratory program in which students perform traditional experiments during the first semester followed by intensive independent work the second semester.
Potter, Neil H.; McGrath, Thomas F. J. Chem. Educ. 1989, 66, 666.
Synthesis |
Alcohols
Azosulfonamides: Preparation and binding to carbonic anhydrase: A bioorganic chemistry experiment  Manalang, Mary G.; Bundy, Hallie F.
Preparation of azosulfonamide, visible absorption analysis of free and enzyme-bond azosulfonamide, and titration of BCA with azosulfonamide.
Manalang, Mary G.; Bundy, Hallie F. J. Chem. Educ. 1989, 66, 609.
Bioorganic Chemistry |
Synthesis |
Proteins / Peptides |
Titration / Volumetric Analysis |
Enzymes
Chemical synthesis of DNA  Caruthers, Marvin H.
Overview of DNA synthesis methodologies and polymer-supported synthesis of DNA using deoxynucleoside phosphoramidites.
Caruthers, Marvin H. J. Chem. Educ. 1989, 66, 577.
Synthesis |
Polymerization
An easy laboratory route to nitrazepam  Babin, P.; Devaux, G.
The laboratory synthesis of nitrazepam, a benzodiazepine.
Babin, P.; Devaux, G. J. Chem. Educ. 1989, 66, 522.
Synthesis |
Drugs / Pharmaceuticals
Synthesis of cobalt(III) "cage" complexes: A twist on an old theme in the inorganic laboratory  Gahan, Lawrence R.; Healy, Peter C.; Patch, Graeme J.
The synthesis described for this compound is particularly attractive as an undergraduate experiment because the complex crystallizes from solution during the preparation removing the necessity of extensive and time-consuming chromatographic purification, which typifies most of these syntheses.
Gahan, Lawrence R.; Healy, Peter C.; Patch, Graeme J. J. Chem. Educ. 1989, 66, 445.
Synthesis
A rapid synthetic method for the preparation of two tris-cobalt(III) compounds  Jackman, Donald C.; Rillema, D. Paul
The authors report a method of preparation of tris(ethylenediamine)cobalt (III) and tris (2,2'-bipyridine)cobalt(III) that will shorten the preparation time by approximately three hours.
Jackman, Donald C.; Rillema, D. Paul J. Chem. Educ. 1989, 66, 343.
Synthesis |
Laboratory Management
Ferrimagnetism   Knox, Kerro
It is possible in a simple lecture demonstration to synthesize Fe3O4 right before student's eyes and to show its interaction with a magnetic field, comparing it to a paramagnetic material.
Knox, Kerro J. Chem. Educ. 1989, 66, 337.
Magnetic Properties |
Synthesis
Friedel Crafts alkylation using elemental aluminum catalyst: An undergraduate laboratory experiment  Meeks, B. Spencer; Lucas, Anita R.
This experiment uses aluminum metal as a catalyst for the synthesis of sec-butyltoluene by Friedel-Crafts alkylation of toluene.
Meeks, B. Spencer; Lucas, Anita R. J. Chem. Educ. 1989, 66, 176.
Alkylation |
Catalysis |
Synthesis
A series of synthetic organic experiments demonstrating physical organic principles  Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H.
The sequence of reactions described here incorporates several common synthetic organic transformations involving alkenes, alcohols, alkyl halides, and ketones that demonstrate some important principles of physical organic chemistry.
Sayed, Yousry; Ahlmark, Chris A.; Martin, Ned H. J. Chem. Educ. 1989, 66, 174.
Synthesis |
Alkenes |
Alcohols |
Aldehydes / Ketones |
Reactions
Synthetic adventure (Williams, Fred D.)  Weber, Paul L.
A software program that is an adventure game which utilizes synthetic organic chemistry to overcome a series of problems or obstacles encountered in the game.
Weber, Paul L. J. Chem. Educ. 1988, 65, A300.
Synthesis
Markownikoff's rule: What did he say and when did he say it?  Tierney, John
The author traces the origin of this important rule.
Tierney, John J. Chem. Educ. 1988, 65, 1053.
Alkenes |
Synthesis
An integrated first-year laboratory experiment involving synthesis, spectroscopy, and chromatography of metal acetylacetonates  Glidewell, Christopher; McKenchnic, James S.
This article presents a comprehensive experiment, involving synthesis, thin-layer chromatography, interpretation of two types of NMR and mass spectra.
Glidewell, Christopher; McKenchnic, James S. J. Chem. Educ. 1988, 65, 1015.
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Separation Science |
Thin Layer Chromatography
Synthesis of azulene, a blue hydrocarbon  Lemal, David M.; Goldman, Glenn D.
A procedure of the synthesis of this simple, beautiful, and theoretically interesting compound with many unusual properties.
Lemal, David M.; Goldman, Glenn D. J. Chem. Educ. 1988, 65, 923.
MO Theory |
Aromatic Compounds |
Diastereomers |
Synthesis
A convenient Schlenk line synthesis of Cr2(OAc)42H20  Young, Charles G.
An experiment that offers an interesting introductory exercise that is well within the capability of students with no Schlenk line technique.
Young, Charles G. J. Chem. Educ. 1988, 65, 918.
Coordination Compounds |
Organometallics |
Synthesis |
Metallic Bonding
A retrosynthetic analogy: Anne's sauteed summer squash  Levy, Irvin J.
Retrosynthetic analysis is a problem-solving methodology that can be used to plan the synthesis of complex organic products using simpler organic reactants as starting materials.
Levy, Irvin J. J. Chem. Educ. 1988, 65, 853.
Synthesis
The preparation of 4-hydroxy-2,3,4,5-tetraphenyl-2-cyclopenten-1-one and its base catalyzed conversion into 2,3,4,5-tetraphenycyclopentadienone: An organic laboratory experiment   Harrison, Ernest A., Jr.
An organic laboratory experiment that permits direct observation of a pedagogically interesting transformation.
Harrison, Ernest A., Jr. J. Chem. Educ. 1988, 65, 828.
Aldehydes / Ketones |
Phenols |
Alkanes / Cycloalkanes |
IR Spectroscopy |
Synthesis
Knoevenagel condensation to alpha-phenylcinnamonitriles: NaBH4 reduction to propanenitriles  Kulp, Stuart S.
The author profiles this fast, simple, condensation that has been utilized for 10 years in their sophomore laboratory course to synthesize unsaturated nitriles in high yields.
Kulp, Stuart S. J. Chem. Educ. 1988, 65, 742.
Synthesis
Example of the Robinson annulation procedure via phase transfer catalysis a beginning organic synthesis experiment  Soriano, D. S.; Lombardi, A. M.; Persichini, P. J.; Nalewajek, D.
A brief description of the procedure.
Soriano, D. S.; Lombardi, A. M.; Persichini, P. J.; Nalewajek, D. J. Chem. Educ. 1988, 65, 637.
Catalysis |
Aromatic Compounds |
Synthesis |
Aldehydes / Ketones
Arylation of carbon carbon double bonds catalyzed by palladium salts  Lauron, Helene; Mallet, Jean-Maurice; Mestdagh, Helene; Ville, Guy
A more advanced synthetic project that incorporates reactions and materials with real-world significance.
Lauron, Helene; Mallet, Jean-Maurice; Mestdagh, Helene; Ville, Guy J. Chem. Educ. 1988, 65, 632.
Applications of Chemistry |
Synthesis |
Alkenes |
Alkanes / Cycloalkanes |
Catalysis
A conversion of methyl ketones into acetylenes: A project for a problem oriented or microscale organic chemistry course  Silveira, Augustine, Jr.; Orlando, Steven C.
The authors present their adaptation of an open-ended project on the conversion of methyl ketones into acetylenes for the microscale lab and describe its pedagogic utility.
Silveira, Augustine, Jr.; Orlando, Steven C. J. Chem. Educ. 1988, 65, 630.
Microscale Lab |
Aldehydes / Ketones |
Synthesis |
Nucleophilic Substitution |
Gas Chromatography
To the editor   Friedmann, Herbert C.
This author defends his article titled, "Energetics of polymerization".
Friedmann, Herbert C. J. Chem. Educ. 1988, 65, 558.
Proteins / Peptides |
Amino Acids |
Synthesis |
Polymerization |
Bioenergetics
Energetics of polymerization: A contribution to an understanding of protein synthesis   Spivack, Jay
A letter attempts to point out inconsistencies in the article "Energetics of polymerization".
Spivack, Jay J. Chem. Educ. 1988, 65, 558.
Proteins / Peptides |
Bioenergetics |
Synthesis |
Amino Acids
Synthesis of benzil from benzoin with copper(II) acetate  Depreux, P.; Bethegnies, G.; Marcincal-Lefebvre, A.
These authors share their development of a synthesis of benzil from benzoin.
Depreux, P.; Bethegnies, G.; Marcincal-Lefebvre, A. J. Chem. Educ. 1988, 65, 553.
Synthesis
Asymmetric Synthesis: Construction of Chiral Molecules Using Amino Acids (Coopola, Gary M.; Schuster, Herbert F.)  Berlin, K. Darrell
Nine chapters, each headed by an amino acid: alanine, phenylalanine, valine, leucine, hydroxy amino acids, sulfur-containing amino acids, difunctional amino acids, proline, and tryptophan.
Berlin, K. Darrell J. Chem. Educ. 1987, 64, A248.
Chirality / Optical Activity |
Synthesis |
Amino Acids
A convenient synthesis of aspartame  Lindeberg, Gunnar
The one tube, enzymatic synthesis of the dipeptide sweetener aspartame.
Lindeberg, Gunnar J. Chem. Educ. 1987, 64, 1062.
Synthesis |
Enzymes |
Proteins / Peptides
A synthesis of chrysanthemic ester: An undergraduate experiment  Kelly, Lawrence F.
Procedure for producing a mixture of cis- and trans-ethyl chrysanthemates.
Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.
Esters |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
Sherlockian distillates  Inman, Charles G.
Investigation of the chemical analysis by Sherlock Holmes in "The Sign of the Four".
Inman, Charles G. J. Chem. Educ. 1987, 64, 1014.
Dyes / Pigments |
Synthesis
The synthesis of an amino acid derivative and spectroscopic monitoring of dipeptide formation  Simmonds, Richard J.
L-alanine is converted to its crystalline N-benzyloxycarbonyl derivative and then esterfied using p-nitrophenol and either dicyclohexylcarbodiimide or ethyl chloroformate.
Simmonds, Richard J. J. Chem. Educ. 1987, 64, 966.
Amino Acids |
Synthesis |
Spectroscopy |
Proteins / Peptides |
Kinetics
A project lab for an advanced general chemistry course featuring the amino acid, glycine  Dudek, Emily P.
Synthesis of glycine, measurement of its nitrogen content by eudiometry, and the estimation of its Rf value as compared to other amino acids using paper chromatography.
Dudek, Emily P. J. Chem. Educ. 1987, 64, 899.
Amino Acids |
Synthesis
Preparation of cyclopentadiene from its dimer  Dickson, Ronald S.; Dobney, Bruce J.; Eastwood, Frank W.
Procedure for preparing cyclopentadiene from its dimer.
Dickson, Ronald S.; Dobney, Bruce J.; Eastwood, Frank W. J. Chem. Educ. 1987, 64, 898.
Alkenes |
Synthesis
Preparation, iodometric analysis, and classroom demonstration of superconductivity in YBa2Cu3O8-x  Harris, Daniel C.; Hills, Marian E.; Hewston, Terrell A.
Student preparation of YBa2Cu3O8-x, a demonstration of its superconductivity, and an analytical experiment dealing with the oxidation state of copper in the material.
Harris, Daniel C.; Hills, Marian E.; Hewston, Terrell A. J. Chem. Educ. 1987, 64, 847.
Superconductivity |
Magnetic Properties |
Oxidation State |
Synthesis
Preparation of lead compounds: An exercise in applied chemistry  Laing, Michael; Williams-Wynn, David; Suhramoney, Saroj
Uses and synthesis of Pb(NO3)2, PbO2, PbCrO4, PbS, PbO, lead carbonate, lead acetate, and lead metal itself.
Laing, Michael; Williams-Wynn, David; Suhramoney, Saroj J. Chem. Educ. 1987, 64, 811.
Synthesis |
Metals |
Oxidation / Reduction |
Oxidation State |
Reactions |
Descriptive Chemistry
Generation of cyclopentadiene  Ruekberg, Benjamin P.
Procedure and apparatus for generating cyclopentadiene.
Ruekberg, Benjamin P. J. Chem. Educ. 1987, 64, 726.
Alkenes |
Synthesis
Unbalanced chemical equations  Jensen, William B.
Analysis of the unbalanced equation representing the production of perchloric acid.
Jensen, William B. J. Chem. Educ. 1987, 64, 646.
Stoichiometry |
Synthesis
Chromium(II) compounds  Silver, G. L.
There is a compound of chromium(II) that can be prepared without elaborate precautions to ensure an oxygen-free atmosphere.
Silver, G. L. J. Chem. Educ. 1987, 64, 646.
Synthesis
Ring opening and ring forming polymerizations: An organic and polymer laboratory experiment  Mathias, Lon J.; Viswnathan, Tito
Polymer synthesis involving ring-opening polymerization to yield a polyamide from oxazoline and cyclopolymerization of a diallylamine derivative to give a polymer containing pyrrolidine units.
Mathias, Lon J.; Viswnathan, Tito J. Chem. Educ. 1987, 64, 639.
Polymerization |
Synthesis |
Heterocycles |
Amides |
Mechanisms of Reactions
Preparation and reaction of 2,2'-bipyridinetetracarbonylmolybdenum(0): An experiment in organometallic photochemistry  Manuta, David M.; Lees, Alistair J.
Synthesis of Mo(CO)4(2,2'-bpy) by photoloysis of a solution containing the parent hexacarbonyl and 2,2'-bipyridine; spectroscopic identification of the product; and an investigation of the photochemistry of this molecule.
Manuta, David M.; Lees, Alistair J. J. Chem. Educ. 1987, 64, 637.
Photochemistry |
Synthesis |
Coordination Compounds
Iron(II) oxide  Miller, Clifford D.
Producing the less common oxide of iron, FeO.
Miller, Clifford D. J. Chem. Educ. 1987, 64, 545.
Synthesis
A new approach to an old experiment  Hansen, Peter J.
Using the synthesis of copper sulfide from its elements to exemplify the concept of theory-laden observations.
Hansen, Peter J. J. Chem. Educ. 1987, 64, 539.
Synthesis
Improved performance in qualitative analysis from incorporating some microscale techniques into a traditional organic laboratory program  Hammond, Christina Noring; Tremelling, Michael J.
Three synthesis experiments in second semester organic that introduce students to microscale techniques in qualitative analysis.
Hammond, Christina Noring; Tremelling, Michael J. J. Chem. Educ. 1987, 64, 440.
Qualitative Analysis |
Microscale Lab |
Synthesis
A convenient synthesis of DCl and HCl-36Cl  Fry, Albert J.
Advantages of using a "Brown hydrogenator" in the synthesis of DCl.
Fry, Albert J. J. Chem. Educ. 1987, 64, 366.
Synthesis |
Laboratory Management |
Nuclear / Radiochemistry
An apparatus permitting constant addition of liquid ammonia in preparative scale ammoniolysis reactions  Carter, Stephen J.
An apparatus that utilizes principles of ammonia distillation to enable a precise volume of liquid ammonia to be delivered at a steady rate under an inert atmosphere.
Carter, Stephen J. J. Chem. Educ. 1987, 64, 365.
Laboratory Equipment / Apparatus |
Synthesis
Preparative exercises in general chemistry  Kauffman, George B.
An excellent "real-life" introduction to descriptive chemistry can be provided by exercises in preparative chemistry, both on paper and in the laboratory.
Kauffman, George B. J. Chem. Educ. 1987, 64, 252.
Descriptive Chemistry |
Synthesis
An organic synthesis program for allied health chemistry  Flash, Patrick
81. Bits and pieces, 33. Organic Reactions Chemistry was written to aid allied health students in learning and codifying organic reactions.
Flash, Patrick J. Chem. Educ. 1987, 64, 238.
Synthesis |
Medicinal Chemistry |
Nonmajor Courses |
Reactions |
Enrichment / Review Materials
An undergraduate experiment in homogeneous catalysis: Synthesis of phenylethoxycarbene tungsten pentacarbonyl and polymerization of norbornene and phenylacetylene  Villemin, Dider
An experiment to illustrate the chemistry of metal carbenes.
Villemin, Dider J. Chem. Educ. 1987, 64, 183.
Synthesis |
Organometallics |
Catalysis
An improved preparation of a Grignard reagent  Eckert, Timothy S.
An improved preparation of phenylmagnesium bromide, a Grignard reagent.
Eckert, Timothy S. J. Chem. Educ. 1987, 64, 179.
Grignard Reagents |
Synthesis
The use of fluoromethanes in organic synthesis  Everett, T. Stephen
A review of advances in selective fluorination; mechanisms and applications of fluoromethanes in organic synthesis.
Everett, T. Stephen J. Chem. Educ. 1987, 64, 143.
Synthesis |
Mechanisms of Reactions
The chemistry of plastics  Deanin, Rudolph D.
The properties and synthesis of common plastics.
Deanin, Rudolph D. J. Chem. Educ. 1987, 64, 45.
Molecular Properties / Structure |
Physical Properties |
Synthesis
Cyclopeptide alkaloids  Bhat, Krishna L.; Joullie, Madeleine M.
The discovery, natural occurrence, isolation, classification, structural determination, properties, and synthesis of selected cyclopeptide alkaloids.
Bhat, Krishna L.; Joullie, Madeleine M. J. Chem. Educ. 1987, 64, 21.
Plant Chemistry |
Natural Products |
Molecular Properties / Structure |
Synthesis
Vinyl chloride as a masked carbonyl group: An experimental project for advanced students  Arnaud, C.; Zakarya, D.
A description of an individual project that can be carried out by an undergraduate who is focusing on organic chemistry. This project shows two classical aspects of problems generally encountered in this field of chemistry.
Arnaud, C.; Zakarya, D. J. Chem. Educ. 1986, 63, 1105.
Reactions |
Synthesis |
Undergraduate Research
The synthesis of lactones from beta-aroylpropionic acids  McGahey, Lawrence
The experiment described in this article gives students experience in a short, multistep syntheses using reactions covered in most elementary organic courses and demonstrates reactions of difunctional compounds.
McGahey, Lawrence J. Chem. Educ. 1986, 63, 1101.
Aromatic Compounds |
Synthesis
Synthesis and evaluation of the sex pheromone of the bagworm moth  Schwarz, Meyer; Klun, J. A.
Several possible student-oriented experiments at different educational levels can look into the interesting chemistry involved in a naturally occurring optically active pheromone.
Schwarz, Meyer; Klun, J. A. J. Chem. Educ. 1986, 63, 1014.
Undergraduate Research |
Natural Products |
Synthesis |
Qualitative Analysis |
Chirality / Optical Activity
Carboxylic acids from halides and carbon dioxide: A facile, fast, inexpensive electrochemical synthesis  Pouliquen, J.; Heintz, M.; Sock, O.; Troupel, M.
In this paper, the authors present an electrosynthesis that takes place in a one compartment cell and necessitates only a very simple constant current generator; the experiment can be run in every undergraduate organic laboratory.
Pouliquen, J.; Heintz, M.; Sock, O.; Troupel, M. J. Chem. Educ. 1986, 63, 1013.
Synthesis |
Electrochemistry
A simple, safe, and easy bromination of alkene using TBABr3: An organic laboratory experiment  Berthelot, Jacques; Fournier, Michel
The authors propose a new and stable brominating reagent, namely tetra-N-butylammonium tribromide because bromine is toxic and corrosive.
Berthelot, Jacques; Fournier, Michel J. Chem. Educ. 1986, 63, 1011.
Synthesis
Microscale organic laboratory: IV: A simple and rapid procedure for carrying out Wittig reactions  Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J.
This paper offers two examples that illustrate a new synthetic method. This synthesis is the first feasible preparation of a particular group available for the introductory organic laboratory.
Pike, R. M.; Mayo, D. W.; Butcher, D. W.; Butcher, S. S.; Hinkle, R. J. J. Chem. Educ. 1986, 63, 917.
Synthesis |
Aromatic Compounds |
Heterocycles |
Alkenes |
Alcohols
Synthesis of fulvenes using phase-transfer catalysis  Hill, John W.; Jenson, Jeffrey A.; Yaritz, Joseph G.
These authors have devised a new procedure for synthesizing fulvenes from indene and fluorene using phase-transfer catalysis.
Hill, John W.; Jenson, Jeffrey A.; Yaritz, Joseph G. J. Chem. Educ. 1986, 63, 916.
Synthesis |
Aromatic Compounds |
Catalysis
The coming renaissance of descriptive chemistry  Zuckerman, J. J.
Inorganic chemistry is facing an identity crises.
Zuckerman, J. J. J. Chem. Educ. 1986, 63, 829.
Descriptive Chemistry |
Spectroscopy |
Synthesis |
Reactions |
Physical Properties |
Solutions / Solvents
Synthesis of 1,2-bis(diphenylphosphino)-ethane: An advanced undergraduate lab  Newman, Alan R.; Hackworth, Craig A.
A popular lab has been modified and one extra step has been added where students need to synthesize a ligand dppe.
Newman, Alan R.; Hackworth, Craig A. J. Chem. Educ. 1986, 63, 817.
Synthesis |
Coordination Compounds
Energetics of polymerization: A contribution to an understanding of protein synthesis  Friedmann, Herbert C.
The author presents an approach to protein synthesis that clarifies some of the conundrums posed by a complex system.
Friedmann, Herbert C. J. Chem. Educ. 1986, 63, 678.
Proteins / Peptides |
Synthesis |
Bioenergetics
The synthesis of 5,5'-diphenylhydantoin: A novel benzil-benzilic acid rearrangement  Pankaskie, Marvin C.; Small, Laverne
A novel benzil-benzilic acid rearrangement.
Pankaskie, Marvin C.; Small, Laverne J. Chem. Educ. 1986, 63, 650.
Synthesis |
Heterocycles |
Mechanisms of Reactions |
Amines / Ammonium Compounds
Synthesis and proton NMR spectrum of p-xylylenebis(2-(2-ethyl-1,3-propanediol))  Lisensky, George C.; Friedman, Robert M.
An experiment that is suitable for a second semester organic class where both the isolation of the product and the NMR spectral interpretation are straightforward.
Lisensky, George C.; Friedman, Robert M. J. Chem. Educ. 1986, 63, 644.
NMR Spectroscopy |
Synthesis
History of Inorganic Syntheses  Fernelius, W. Conard
This article provides an examination of the growth of this branch of chemistry over the course of the past decades.
Fernelius, W. Conard J. Chem. Educ. 1986, 63, 500.
Synthesis
Synthesis with ultrasonic waves  Boudjouk, Philip
A historical overview of the use of ultrasonic waves for chemical synthesis.
Boudjouk, Philip J. Chem. Educ. 1986, 63, 427.
Synthesis |
Aromatic Compounds |
Alkanes / Cycloalkanes |
Reactions |
Catalysis
The production and recovery of C2-C4 olefins from syngas  Murchison, C. H.; Weiss, R. L.; Stowe, R. A.
Authors from Dow Chemical present ways of preparing C2-C4 alkenes from synthesis gas using heterogeneous catalysis.
Murchison, C. H.; Weiss, R. L.; Stowe, R. A. J. Chem. Educ. 1986, 63, 213.
Alkenes |
Synthesis |
Gases
A convenient synthesis of alpha, beta-butenolide: An organic chemistry laboratory experiment  Vijayaraghavan, S. T.; Balasubramanian, T. R.
An organic chemistry synthesis laboratory experiment.
Vijayaraghavan, S. T.; Balasubramanian, T. R. J. Chem. Educ. 1986, 63, 156.
Synthesis
Mushroom odors: Student synthesis of the odoriferous compounds of the matsutake mushroom  Wood, William F.; Fesler, Mark
Matsutake mushrooms are in demand due to their pleasant and appetizing flavor or aroma. This article describes the synthesis of methyl cinnamate as an experiment for the undergraduate organic chemistry laboratory.
Wood, William F.; Fesler, Mark J. Chem. Educ. 1986, 63, 92.
Food Science |
Synthesis |
Aromatic Compounds |
Natural Products
Total Synthesis of Natural Products: The 'Chiron' Approach (Hanessian, Stephen)  Wade, Leroy G., Jr.
Details the use of carbohydrate derivatives as chiral starting points for the synthesis of chiral products.
Wade, Leroy G., Jr. J. Chem. Educ. 1985, 62, A190.
Natural Products |
Synthesis |
Carbohydrates |
Chirality / Optical Activity
Heterocycles and reactive intermediates in the undergraduate organic lab  Bowles, K. Dean; Quincy, David; Mallet, Brenda; McKenna, John I.; Natale, N. R.
The nitrile oxide cycloaddition with enamines is useful in illustrating the concepts of reactive intermediates in synthesis and frontier molecular orbital theory.
Bowles, K. Dean; Quincy, David; Mallet, Brenda; McKenna, John I.; Natale, N. R. J. Chem. Educ. 1985, 62, 1118.
Heterocycles |
Synthesis |
Reactive Intermediates |
MO Theory
And the winner is . . . A multistep synthesis for the introductory organic course  Stradling, Samuel S.; Gage, Clarke L.
A synthetic sequence with a touch of friendly competition; methyl m-nitrobenzoate is prepared via three different routes from acetophenone.
Stradling, Samuel S.; Gage, Clarke L. J. Chem. Educ. 1985, 62, 1116.
Synthesis |
Aromatic Compounds
Chemical dominos: How NOT to get lost in the shuffle  Garrett, James M.
A game for teaching introductory retrosynthetic analysis.
Garrett, James M. J. Chem. Educ. 1985, 62, 1102.
Enrichment / Review Materials |
Synthesis
Graphics drill and game programs for benzene synthesis  Flash, Patrick J.
65. Bits and pieces, 26. "Benzene Synthesis Drill", a game format program that drills students on multistep conversions involving benzene.
Flash, Patrick J. J. Chem. Educ. 1985, 62, 1028.
Enrichment / Review Materials |
Aromatic Compounds |
Synthesis
Synthesis of 3,4-dihydro-3-(p-methylphenyl)-1,3,2H-benzoxazine: An undergraduate organic chemistry experiment  Iskander, Magdy N.; Andrews, Peter R.
Synthesis involves an analog of several biologically active molecules.
Iskander, Magdy N.; Andrews, Peter R. J. Chem. Educ. 1985, 62, 913.
Synthesis
Phase-transfer-catalyzed alkylation of ethyl acetoacetate and diethyl malonate  Thompson, Douglas L.; Reeves, Perry C.
Improved method that requires shorter reaction times and safer reagents than traditional procedures.
Thompson, Douglas L.; Reeves, Perry C. J. Chem. Educ. 1985, 62, 907.
Catalysis |
Mechanisms of Reactions |
Synthesis
A simplified method to prepare 2-amino-5-bromopyrimidine: A laboratory experiment  Fichter, Richard; Bonvicino, Guido E.
The procedure eliminates the use of liquid bromine, acidic solvents, and elevated temperatures.
Fichter, Richard; Bonvicino, Guido E. J. Chem. Educ. 1985, 62, 905.
Synthesis
Preparation and characterization of myosin proteins  Caldwell, Elizabeth; Eftink, Maurice R.
Each student or team of lab partners is responsible for one of five projects involving the isolation and characterization of rabbit myosin proteins and its water-soluble subfragments.
Caldwell, Elizabeth; Eftink, Maurice R. J. Chem. Educ. 1985, 62, 900.
Synthesis |
Proteins / Peptides |
Electrophoresis |
Enzymes
A better way to prepare DCl  Hollenberg, J. Leland
Generating DCl from D2SO4.
Hollenberg, J. Leland J. Chem. Educ. 1985, 62, 897.
Isotopes |
Synthesis |
Nuclear / Radiochemistry
Synthesis of organometallic palladium complexes: An undergraduate experiment  Bailey, Christopher T.; Lisensky, George C.
Procedure for the synthesis of organometallic palladium complexes containing both sigma and pi metal-carbon bonds.
Bailey, Christopher T.; Lisensky, George C. J. Chem. Educ. 1985, 62, 896.
Synthesis |
Organometallics |
Coordination Compounds
The production of oxygen gas: A student catalysis experiment  Onuchukwu, A. I.; Mshelia, P. B.
Synthesizing copper ferrite spinnel and using it as a catalyst in the decomposition of hydrogen peroxide to generate oxygen; the rate of generation is used to determine the kinetic activity of the catalyst.
Onuchukwu, A. I.; Mshelia, P. B. J. Chem. Educ. 1985, 62, 809.
Catalysis |
Synthesis |
Kinetics
Facile synthesis of a macrobicyclic hexaamine cobalt(III) complex based on tris(ethylenediamine)cobalt(III): An advanced undergraduate inorganic laboratory experiment  Harrowfield, Jack MacB.; Lawrence, Geoffrey A.; Sargeson, Alan M.
The synthesis and characterization of a macrobicyclic complex.
Harrowfield, Jack MacB.; Lawrence, Geoffrey A.; Sargeson, Alan M. J. Chem. Educ. 1985, 62, 804.
Synthesis |
Coordination Compounds
Ultrasound in the undergraduate lab  Lash, Timothy D.
Applying ultrasound to Grignard reactions and the Baeyer test.
Lash, Timothy D. J. Chem. Educ. 1985, 62, 720.
Synthesis |
Grignard Reagents
Synthesis and a simple molecular weight determination of polystyrene  Armstrong, Daniel W.; Marx, John N.; Kyle, Don; Alak, Ala
Procedure for synthesizing styrene and determining its molecular weight using thin layer chromatography.
Armstrong, Daniel W.; Marx, John N.; Kyle, Don; Alak, Ala J. Chem. Educ. 1985, 62, 705.
Synthesis |
Polymerization |
Chromatography
Preparation of the bromohydrin of 3-sulfolene  Greenberg, Fred H.
Reaction of N-bromosuccinimide with 3-sulfolene.
Greenberg, Fred H. J. Chem. Educ. 1985, 62, 638.
Synthesis |
Alkenes
The nitric acid oxidation of selected alcohols and ketones: An organic laboratory experiment  Field, Kurt, W.; Shields, James P.; Standard, Jean M.; Ash, Craig K.; Hoch, Daniel J.; Kolb, Kenneth E.
Preparation of C6-C12 a, ?-dioic acids, glutaric acid, and substituted benzaldehydes and benzophenones.
Field, Kurt, W.; Shields, James P.; Standard, Jean M.; Ash, Craig K.; Hoch, Daniel J.; Kolb, Kenneth E. J. Chem. Educ. 1985, 62, 637.
Alcohols |
Aldehydes / Ketones |
Oxidation / Reduction |
Synthesis
Synthesis and multinuclear lanthanide shift reagent NMR analysis of 1- and 2-adamantanol: An advanced undergraduate laboratory project  Schaeffer, Charles D., Jr.; Yoder, Claude. H.
Preparation of two alcohols, their characterization, and the use of a shift reagent for structure determination and peak assignment.
Schaeffer, Charles D., Jr.; Yoder, Claude. H. J. Chem. Educ. 1985, 62, 537.
Synthesis |
NMR Spectroscopy |
Alcohols
The preparation of benzoyl esters of phenols and benzoic anhydride by phase-transfer catalysis  Yeadon, A.; Turney, T. A.; Ramsay, G.
The procedure is sufficiently rapid to replace the Schotten-Baumann technique.
Yeadon, A.; Turney, T. A.; Ramsay, G. J. Chem. Educ. 1985, 62, 518.
Synthesis |
Catalysis |
Esters |
Phenols |
Aromatic Compounds
4,5-diphenyl-1-methylimidazole: An undergraduate laboratory experiment  Anastas, Paul T.; Kano, Kunio; Anselme, Jean-Pierre
Procedure for the synthesis of 4,5-diphenyl-1-methylimidazole heterocycle.
Anastas, Paul T.; Kano, Kunio; Anselme, Jean-Pierre J. Chem. Educ. 1985, 62, 515.
Heterocycles |
Synthesis
A critical point  Gonzalez, Orestes J.
Some troublesome gaps in the theory of evolution have been overlooked.
Gonzalez, Orestes J. J. Chem. Educ. 1985, 62, 503.
Synthesis |
Chirality / Optical Activity |
Stereochemistry
Preparation and properties of cholesteric liquid crystals  Patch, Graeme; Hope, Gregory A.
Synthesis and characterization of cholesterol compounds and the study of their liquid crystal properties as a function of temperature and composition.
Patch, Graeme; Hope, Gregory A. J. Chem. Educ. 1985, 62, 454.
Synthesis
Tris(oxalato) teaching aids  Young, Charles G.
Preparation and characterization of potassium tris(oxalato)ferrate(III).
Young, Charles G. J. Chem. Educ. 1985, 62, 445.
Synthesis |
IR Spectroscopy |
X-ray Crystallography |
Magnetic Properties
A simple homogeneous precipitation preparation of chromium(II) acetate  Reeve, John C.
Preparation of Cr(II) acetate as an example of an exercise requiring the use of oxygen-free atmosphere techniques.
Reeve, John C. J. Chem. Educ. 1985, 62, 444.
Precipitation / Solubility |
Synthesis
Microcomputer-assisted drills in organic synthesis  Barone, R.; Ribero, B.; Gibert, B.; Meyer, R.
60. Bits and pieces, 23. Tests students on organic syntheses.
Barone, R.; Ribero, B.; Gibert, B.; Meyer, R. J. Chem. Educ. 1985, 62, 411.
Synthesis |
Enrichment / Review Materials
The Wittig reaction in the undergraduate organic laboratory  Warner, John C.; Anastas, Paul T.; Anselme, Jean-Pierre
Using phase-transfer catalysis to prepare cis- and trans-stilbenes from the Wittig condensation of benzaldehyde.
Warner, John C.; Anastas, Paul T.; Anselme, Jean-Pierre J. Chem. Educ. 1985, 62, 346.
Mechanisms of Reactions |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
Phosphorus and sulfur ylide formation: Preparation of 1-benzoyl-2-phenylcyclopropane and 1,4-diphenyl-1,3-butadiene by phase transfer catalysis  Lampman, Gary M.; Koops, Roger W.; Olden, Caroline C.
The phase transfer catalysis reaction can be used to prepare 1-benzoyl-2-phenylcyclopropane in about 80% yield in one hour from trimethyloxosulfonium iodide and benzalacetophenone.
Lampman, Gary M.; Koops, Roger W.; Olden, Caroline C. J. Chem. Educ. 1985, 62, 267.
Synthesis |
Catalysis
Electrocyclic ring opening of halocyclopropanes  Markgraf, J. Hodge; Finkelstein, Manuel; Leonard, Kathryn J.; Lusskin, Shari I.
An experiment that demonstrates the stereospecific rearrangement of cyclopropyl halides to allylic halides.
Markgraf, J. Hodge; Finkelstein, Manuel; Leonard, Kathryn J.; Lusskin, Shari I. J. Chem. Educ. 1985, 62, 265.
Synthesis |
Stereochemistry
The synthesis of 1-phenyl-1,2,3,4-tetrahydroisoquinolines: An undergraduate organic laboratory experiment and class project  Letcher, R. M.; Sammes, M. P.
Uses the Pictet-Spengler route and gives students the opportunity to study the spectra of alkaloid-type materials.
Letcher, R. M.; Sammes, M. P. J. Chem. Educ. 1985, 62, 262.
Synthesis |
Heterocycles
Determination of the metal-metal distance in the mixed valence complex K2Pt(CN)4BO 33H2O  Sedney, Diana L.; Tanner, Martin
Once synthesized, the Pt-Pt distance in this compound is determined using X-ray diffraction.
Sedney, Diana L.; Tanner, Martin J. Chem. Educ. 1985, 62, 254.
Coordination Compounds |
Synthesis |
X-ray Crystallography |
Crystals / Crystallography
Promotion of organic reactions by ultrasound: Coupling of alkyl and aryl halides in the presence of lithium metal and ultrasound  Lash, Timothy D.; Berry, Donna
Bromopropane, bromobutane, and bromopentane were found to react vigorously with lithium in ether solution when bombarded with ultrasound to give hexane, octane, and decane, but little reaction took place in the absence of sonication.
Lash, Timothy D.; Berry, Donna J. Chem. Educ. 1985, 62, 85.
Synthesis
Concerning the syntheses and structure of 2,3-dihydro-1,4-diphenyl-2,3-triphenylenedicarboxylic anhydride  Baxter, Alexis V.; Hangeland, Jon J.; Harrison, Ernest A., Jr.
An earlier published synthesis is not a realistic goal for undergraduates.
Baxter, Alexis V.; Hangeland, Jon J.; Harrison, Ernest A., Jr. J. Chem. Educ. 1985, 62, 79.
Synthesis
Organic Synthesis: The Disconnection Approach (Warren, Stuart)  Wade, L. G., Jr.
Textbook for an introductory course in organic synthesis for graduate students and senior undergraduates.
Wade, L. G., Jr. J. Chem. Educ. 1984, 61, A248.
Synthesis
Oxidation of alcohols using calcium hypochlorite and solid/liquid phase-transfer catalysis  Hill, John W.; Jenson, Jeffrey A.; Henke, Charles F.; Yaritz, Joseph G.; Pedersen, Richard L.
Includes synthesis of an aldehyde from a primary alcohol as well as several ketones from secondary alcohols.
Hill, John W.; Jenson, Jeffrey A.; Henke, Charles F.; Yaritz, Joseph G.; Pedersen, Richard L. J. Chem. Educ. 1984, 61, 1118.
Alcohols |
Oxidation / Reduction |
Catalysis |
Aldehydes / Ketones |
Synthesis
Synthesis and spectra of vanadium complexes  Ophardt, Charles E.
Vanadium complexes provide good examples that illustrate the use of Orgel diagrams for the interpretation of electronic transition-metal spectra.
Ophardt, Charles E. J. Chem. Educ. 1984, 61, 1102.
Coordination Compounds |
Synthesis |
Oxidation State |
Metals
Preparation of a phosphor, ZnA:Cu2+  Suib, Steveu L.; Tauaka, John
This experiment exposes students to the preparation of a doped semiconductor, phosphorescence, gettering procedures, reducing atmospheres, and the use of a high temperature furnace with associated thermocouples, temperature controllers, and temperature-sensing devices.
Suib, Steveu L.; Tauaka, John J. Chem. Educ. 1984, 61, 1099.
Synthesis |
Semiconductors |
Solid State Chemistry
Preparation and analysis of potassium tris(oxalato)ferrate(III)trihydrate: A general chemistry experiment  Olmsted, John, III
The analysis of this compound combines gravimetric and titrimeric methods and includes a unique and colorful photoredox reaction.
Olmsted, John, III J. Chem. Educ. 1984, 61, 1098.
Synthesis |
Photochemistry |
Oxidation / Reduction |
Gravimetric Analysis |
Titration / Volumetric Analysis
Paul Klee and the genesis of deltic and squaric acids  Serratosa, Felix
The mental process leading to the synthesis of deltic and squaric acids is essentially identical to that of the pathways leading to the genesis of the triangle and square as visualized by the painter Paul Klee.
Serratosa, Felix J. Chem. Educ. 1984, 61, 1035.
Acids / Bases |
Synthesis
Preparation of 2-bromopentane  Howell, B. A.; Kohrman, R. E.
The conversion of 2-pentanol to 2-bromopentane offers a good illustration of the problems associated with substitution in secondary systems.
Howell, B. A.; Kohrman, R. E. J. Chem. Educ. 1984, 61, 932.
Synthesis |
Alkanes / Cycloalkanes
Laboratory syntheses of insect pheromones  Cormier, Russell A.; Hoban, James N.
Synthesis of the sex attractants of the tiger moth and boll weevil.
Cormier, Russell A.; Hoban, James N. J. Chem. Educ. 1984, 61, 927.
Natural Products |
Synthesis
Antimetabolites of coenzyme Q and their potential clinical use as antitumor agents: A new biochemical approach to cancer chemotherapy  Folkers, Karl; Porter, Thomas H.
Discovery of coenzyme Q10, synthesis of antimetabolites of coenzyme Q10, and two promising classes of coenzyme Q10 analogs as potential antitumor agents.
Folkers, Karl; Porter, Thomas H. J. Chem. Educ. 1984, 61, 892.
Enzymes |
Medicinal Chemistry |
Synthesis
The synthesis and methanolysis of benzyl tosylates: An advanced organic chemistry laboratory experiment  Garst, Michael E.; Gribble, Gordon W.
A class-project experiment that contains both synthesis and a physical-organic chemical study and affords the student opportunities to measure, manipulate, and evaluate his/her data.
Garst, Michael E.; Gribble, Gordon W. J. Chem. Educ. 1984, 61, 819.
Synthesis
Synthesis of frontalin, the aggregation phermone of the southern pine beetle  Bartlett, Paul A.; et al.
The multistep synthesis of frontalin outlined exposes students to a range of practical laboratory problems.
Bartlett, Paul A.; et al. J. Chem. Educ. 1984, 61, 816.
Natural Products |
Synthesis
Nylon 6 - A simple, safe synthesis of a tough commercial polymer  Mathias, Lon J.; Vaidya, Rajeev A.; Canterberry, J. B.
An improved procedure for the synthesis of Nylon 6 that is easier, safer, and gives a product with impressive strength.
Mathias, Lon J.; Vaidya, Rajeev A.; Canterberry, J. B. J. Chem. Educ. 1984, 61, 805.
Polymerization |
Synthesis
Synthesis and testing of the insecticide carbaryl  Thadeo, Peter F.; Mowery, Dwight F.
Carbaryl, 1-naphthyl-N-methylcarbamate, is synthesized from alpha-naphthol and triethylamine.
Thadeo, Peter F.; Mowery, Dwight F. J. Chem. Educ. 1984, 61, 742.
Synthesis |
Applications of Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds
Metallo complexes: An experiment for the undergraduate laboratory  Kauffman, George B.; Karbassi, Mohammad; Bergerhoff, Gunter
Theory, nomenclature, structure, and preparative methods of metallic complexes; the experiment prepares several metallo complexes according to procedures modified from the literature and their properties are observed.
Kauffman, George B.; Karbassi, Mohammad; Bergerhoff, Gunter J. Chem. Educ. 1984, 61, 729.
Coordination Compounds |
Metals |
Nomenclature / Units / Symbols |
Molecular Properties / Structure |
Synthesis
Preparation of 4-phenylbut-3-yn-2-one: An organic chemistry project  Wollard, J. M.
An experiment that avoids the use of liquid ammonia and of ethyne, yet illustrates the acidity of terminal alkynes and the use of the resulting anion to form new carbon-carbon bonds.
Wollard, J. M. J. Chem. Educ. 1984, 61, 648.
Synthesis |
Alkynes |
Mechanisms of Reactions
The synthesis and characterization of some fluoride perovskites, an undergraduate experiment in solid state chemistry  Langley, Richard H.; Schmitz, Colleen K.; Langley, Maureen B.
Characterization is through density, X-ray diffraction, and magnetic susceptibility.
Langley, Richard H.; Schmitz, Colleen K.; Langley, Maureen B. J. Chem. Educ. 1984, 61, 643.
Synthesis |
Solid State Chemistry |
Magnetic Properties
Possible existence of cesium neonide  Borrows, T. P.
The cited authors are wrong to suggest that there has been no consideration of the possible existence of compounds of the noble gases with electropositive substances.
Borrows, T. P. J. Chem. Educ. 1984, 61, 566.
Synthesis
Metalloporphyrins  Maitland, M. S.; Langley, R. H.
A useful addition to the cited experiment.
Maitland, M. S.; Langley, R. H. J. Chem. Educ. 1984, 61, 566.
Organometallics |
Synthesis
Synthesis of benzoic acid using household bleach  Perkins, Robert
Conversion of acetophenone to benzoic acid (the haloform reaction) using household bleach.
Perkins, Robert J. Chem. Educ. 1984, 61, 551.
Synthesis |
Carboxylic Acids |
Aromatic Compounds
Uses of a vinylpyridine polymer in undergraduate organic synthesis  Getman, Damon; Hagerty, David; Wilson, George; Wood, William F.
Applications of poly-4-vinylpyridine in a number of organic synthesis reactions.
Getman, Damon; Hagerty, David; Wilson, George; Wood, William F. J. Chem. Educ. 1984, 61, 550.
Synthesis
Teaching of chemical reactions and syntheses  Basolo, Fred
We are obliged to teach students some fundamental reactions that all chemists should know.
Basolo, Fred J. Chem. Educ. 1984, 61, 520.
Reactions |
Synthesis
An undergraduate laboratory experiment: The total synthesis of maytansine  Goodwin, Thomas E.
Guidelines pertaining to the de novo establishment of an undergraduate research program in a small college. From the symposium "Undergraduate Research as Chemical Education".
Goodwin, Thomas E. J. Chem. Educ. 1984, 61, 511.
Conferences |
Undergraduate Research |
Synthesis |
Natural Products
Concertedness of 1,3-dipolar cycloadditions  Haque, M. Serajul
The 1,3-dipolar cycloaddition is the union of a 1,3-dipole with a multiple bond system (a dipolarophile) to form a five-membered ring; the process is regarded as one of the most general methods for the synthesis of five-membered heterocycles.
Haque, M. Serajul J. Chem. Educ. 1984, 61, 490.
Addition Reactions |
Alkanes / Cycloalkanes |
Mechanisms of Reactions |
Heterocycles |
Synthesis |
MO Theory
Preparation of a stoichiometric complex of hydronium tetrafluoroborate and 18-crown-6 by phase transfer  Chenevert, Robert; Rodrique, Andre
Involves the preparation of a one-to-one stoichiometric complex of a hydronium ion with the macrocyclic ether, 8-crown-6, by transfer of the hydronium ion from aqueous solution to an organic phase.
Chenevert, Robert; Rodrique, Andre J. Chem. Educ. 1984, 61, 465.
Synthesis |
Coordination Compounds
A new method for the preparation of derivatives of carboxylic acids  Brindle, Ian D.; Chassie, Susan
Preparation technique using potassium fluoride. From the "State-of-the-Art Symposium for Chemical Educators: Chemistry of the Food Cycle".
Brindle, Ian D.; Chassie, Susan J. Chem. Educ. 1984, 61, 347.
Synthesis |
Carboxylic Acids
Synthesis of vitamin K epoxide: An undergraduate biochemistry experiment  Thierry-Palmer, M.
A metabolite of vitamin K, its 2,3-epoxide, is synthesized and purified.
Thierry-Palmer, M. J. Chem. Educ. 1984, 61, 179.
Vitamins |
Synthesis |
Lipids
A convenient method for the preparation of 2,4-dinitrophenylhydrazones  Howell, B. A.
A more satisfactory synthesis that increases the conversion rate and minimizes undesired side reactions.
Howell, B. A. J. Chem. Educ. 1984, 61, 176.
Synthesis |
Aldehydes / Ketones
The prototype compound for the oral anticoagulants  Hayward, Rodney C.
The courmarin anticoagulants provide illustrative, carbanion-mediated, bond-forming reactions and interesting target heterocycles for synthesis.
Hayward, Rodney C. J. Chem. Educ. 1984, 61, 87.
Medicinal Chemistry |
Heterocycles |
Synthesis
Guidebook to organic synthesis (Mackie, R.K.;Smith, D.M.)  Wade, L. G., Jr.
A review of a text that was designed as a text for an advanced undergraduate course in organic synthesis.
Wade, L. G., Jr. J. Chem. Educ. 1983, 60, A320.
Synthesis
Synthesis of potassium tris(oxalato)-aluminate(III) trihydrate  McNeese, Timothy J.; Wierda, Derk A.
A brief description for a procedure for Synthesis of potassium tris(oxaiato)-aluminate(III) trihydrate.
McNeese, Timothy J.; Wierda, Derk A. J. Chem. Educ. 1983, 60, 1001.
Synthesis |
Coordination Compounds
A study on amino acids: synthesis of alpha-aminophenylacetic acid(phenylglycine) and determination of its isoelectric point  Barrelle, M.; Gaude, D.; Salon, M. C.
These authors are proposing a study on aminophenylacetic acid because a project concerning pharmaceutical or natural products is always attractive to students.
Barrelle, M.; Gaude, D.; Salon, M. C. J. Chem. Educ. 1983, 60, 676.
Drugs / Pharmaceuticals |
Natural Products |
Acids / Bases |
Titration / Volumetric Analysis |
Synthesis
Synthetic petroleum from coal hydrogenation: its history and present state of development in the United States  Stranges, Anthony N.
This author has reviewed the history of attempts to hydrogenate coal.
Stranges, Anthony N. J. Chem. Educ. 1983, 60, 617.
Alkanes / Cycloalkanes |
Synthesis |
Applications of Chemistry |
Industrial Chemistry
Synthesis of the anticonvulsant drug 5,5-diphenylhydantoin: an undergraduate organic chemistry experiment  Hayward, Rodney C.
The hydantions are a drug family lying within the broadly related ureide structural frame which encompasses many of the anticonvulsant drugs used in the treatment of the various types of epilepsy.
Hayward, Rodney C. J. Chem. Educ. 1983, 60, 512.
Drugs / Pharmaceuticals |
Synthesis
The synthesis of 4,6,8-trimethylazulene: an organic laboratory experiment  Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott
A procedure for a two-step synthesis of 4,6,8-trimethylazulene.
Garst, Michael E.; Hochlowski, Jill; Douglass, III, James G.; Sasse, Scott J. Chem. Educ. 1983, 60, 510.
Synthesis |
Heterocycles |
Aromatic Compounds |
Resonance Theory |
Chromatography
A study of stereospecificity: the Beckmann rearrangement  Stradling, S. S.; Hornick, D.; Lee, J.; Riley, J.
These authors have developed a Beckmann rearrangement which explores the concept of stereospecificity, and concurrently exposes the student to synthetic, spectrometric, and chromatographic processes for an advanced laboratory.
Stradling, S. S.; Hornick, D.; Lee, J.; Riley, J. J. Chem. Educ. 1983, 60, 502.
Synthesis |
Chromatography |
Spectroscopy |
Stereochemistry |
Aldehydes / Ketones |
NMR Spectroscopy |
Alkenes |
Phenols
Industrial organic electrosynthesis  Wagenknecht, John H.
This article profiles some common and important electrochemical syntheses of organic compounds in industry. From State-of-the-Art Symposium: Electrochemistry, ACS meeting, Kansas City, 1982.
Wagenknecht, John H. J. Chem. Educ. 1983, 60, 271.
Industrial Chemistry |
Electrochemistry |
Synthesis |
Applications of Chemistry
Electrosynthesis technology  Weinberg, Norman L.
An examination of introductory general chemistry textbooks lead this author to believe that the majority of chemistry and chemical engineering students gain an inadequate awareness of electrosynthesis principles and technology. This article describes an activity that will give students a greater exposure to electrosynthesis reactions. From State-of-the-Art Symposium: Electrochemistry, ACS meeting, Kansas City, 1982.
Weinberg, Norman L. J. Chem. Educ. 1983, 60, 268.
Electrochemistry |
Synthesis |
Oxidation / Reduction
3-Ketoesters by malonic synthesis  Pollet, Patrick L.
This essay reviews a synthesis strategy.
Pollet, Patrick L. J. Chem. Educ. 1983, 60, 244.
Synthesis |
Carboxylic Acids |
Aldehydes / Ketones |
Alkylation
Highly stereoselective synthesis and rearrangement of beta-amino alpha-bromo chalcones  Arnould, J. C.; Feigenbaum, A.; Henin, F.
The authors propose an experiment for advanced students which involves a sequence of easy steps illustrating important reactions and concepts of organic chemistry.
Arnould, J. C.; Feigenbaum, A.; Henin, F. J. Chem. Educ. 1983, 60, 82.
Synthesis |
Stereochemistry |
Amino Acids |
Phenols |
Synthesis |
Aromatic Compounds
Organic chemicals from carbon monoxide  Kolb, Kenneth E.; Kolb, Doris
Looking at organic chemicals and their reactions with carbon monoxide has a great pedagogical value.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1983, 60, 57.
Synthesis |
Reactions
Chemistry of Free Atoms and Particles (Klabunde, Kenneth J.)  Adcock, James L.
Considers the field of metal vapor synthesis.
Adcock, James L. J. Chem. Educ. 1982, 59, A28.
Metals |
Surface Science |
Synthesis |
Gases
The synthesis and chemiluminescence of stable 1,2-dioxetane: An organic chemistry laboratory experiment  Meijer, E. W.; Wynberg, Hans
The synthesis and chemiluminescence of adamantylideneadamantane-1,2-dioxetane.
Meijer, E. W.; Wynberg, Hans J. Chem. Educ. 1982, 59, 1071.
Photochemistry |
Synthesis
Preparation of propyl N,N-diethylsuccinimate: An insect repellent  Caudle, Robert; Siegel, Gretta; Wood, William F.
Synthesis of propyl N,N-diethylsuccinimate, a relatively safe and effective insect repellent.
Caudle, Robert; Siegel, Gretta; Wood, William F. J. Chem. Educ. 1982, 59, 1069.
Synthesis |
Applications of Chemistry
Cyclohexanol dehydration: A simple experiment in heterogeneous catalysis  Costa, A.
Catalytic synthesis of cyclohexene and various cyclopentenes from cyclohexanol.
Costa, A. J. Chem. Educ. 1982, 59, 1066.
Catalysis |
Synthesis |
Alcohols |
Alkenes
Some experiments in sulfur-nitrogen chemistry  Banister, Arthur J.; Smith, Nigel
A survey of the main structural types of sulfur-nitrogen compounds, and syntheses suitable for undergraduate experiments, that illustrate four of the five types of cyclic species.
Banister, Arthur J.; Smith, Nigel J. Chem. Educ. 1982, 59, 1058.
Molecular Properties / Structure |
Synthesis
The monomeric pentacyanocobaltate(II) anion: Preparation and properties of thallium(I) pentacyanocobaltate(II)  Mosha, Donnati M. S.
The synthesis and characterization of thallium(I) pentacyanocobaltate(II).
Mosha, Donnati M. S. J. Chem. Educ. 1982, 59, 1057.
IR Spectroscopy |
Synthesis
The study of a cobalt complex - a laboratory project  Loehlin, James H.; Kahl, Stephen B.; Darlington, Jeanne A.
The laboratory involves synthesis followed by qualitative and quantitative analysis of either Co(NH3)5Cl3 or C0(NH3)6Cl3 over several weeks.
Loehlin, James H.; Kahl, Stephen B.; Darlington, Jeanne A. J. Chem. Educ. 1982, 59, 1048.
Coordination Compounds |
Magnetic Properties |
Qualitative Analysis |
Quantitative Analysis |
Synthesis
Ketone synthesis using household bleach  Perkins, Robert A.; Chau, Felix
Household bleach is used to synthesize several different ketones from alcohols.
Perkins, Robert A.; Chau, Felix J. Chem. Educ. 1982, 59, 981.
Synthesis |
Aldehydes / Ketones |
Alcohols
The photochemical synthesis, kinetics, and reactions of nitrosomethane dimer: A physical-organic experiment  Kozubek, H.; Marciniak, B.; Paszyc, S.
Determines the quantum yields of trans nitrosomethane dimer disappearance and cis dimer formation.
Kozubek, H.; Marciniak, B.; Paszyc, S. J. Chem. Educ. 1982, 59, 889.
Photochemistry |
Synthesis |
Kinetics
An NMR kinetics experiment  Kaufman, Don; Sterner, Carl; Masek, Brian; Svenningsen, Ralph; Samuelson, Greg
Uses NMR spectroscopy to obtain rate data for the synthesis of p-methoxyphenylacetylene.
Kaufman, Don; Sterner, Carl; Masek, Brian; Svenningsen, Ralph; Samuelson, Greg J. Chem. Educ. 1982, 59, 885.
NMR Spectroscopy |
Kinetics |
Catalysis |
Synthesis |
Mechanisms of Reactions |
Rate Law
Student preparation of acetone from 2-propanol  Kauffman, J. M.; McKee, J. R.
Using swimming pool chlorine for the oxidation of 2-propanol to acetone.
Kauffman, J. M.; McKee, J. R. J. Chem. Educ. 1982, 59, 862.
Aldehydes / Ketones |
Alcohols |
Synthesis |
Oxidation / Reduction
A catalyst for the synthesis of soap  Hill, John W.; Soldberg, Sherrie J.; Hill, Cynthia S.
Use of a catalyst allows soap to be synthesized overnight at room temperature.
Hill, John W.; Soldberg, Sherrie J.; Hill, Cynthia S. J. Chem. Educ. 1982, 59, 788.
Catalysis |
Synthesis |
Consumer Chemistry
TRS-80 simulation of a vacuum system synthesis  Whisnant, David M.
32. Bits and pieces, 12.
Whisnant, David M. J. Chem. Educ. 1982, 59, 779.
Synthesis
Synthesis of Photochromic 2-(2,4-Dinitrobenzyl)pyridine  Zaczek, Norbert M.; Levy, W. David; Jordan, Michael L.; Niemyer, Judith A.
A small scale procedure for the nitration of 2-benzylpyridine to yield the reversibly photochromic compound 2-(2,4-dinitrobenzyl)-pyridine using fuming nitric acid.
Zaczek, Norbert M.; Levy, W. David; Jordan, Michael L.; Niemyer, Judith A. J. Chem. Educ. 1982, 59, 705.
Synthesis
An easy synthesis of two cage hydrocarbons  Dong, Dao Cong
A three-step synthesis of two cage molecules, birdcage hydrocarbon and its homologue, the homobirdcage hydrocarbon.
Dong, Dao Cong J. Chem. Educ. 1982, 59, 704.
Synthesis
The synthesis of a dipeptide from its component amino acids: Protecting groups in the elementary organic laboratory  Young, Paul E.; Campbell, Andrew
A three-step procedure for synthesizing a dipeptide from its component amino acids.
Young, Paul E.; Campbell, Andrew J. Chem. Educ. 1982, 59, 701.
Synthesis |
Amino Acids |
Proteins / Peptides
An easy student synthesis of a substituted 1,3-dioxane by use of an ion-exchange resin as catalyst: Clean illustration of the Prins reaction  Delmas, Michel; Kalck, Phillipe; Gorrichon, Jean-Pierre; Gaset, A.
The preparation of 4-(4-hydroxy, 3-methoxy-phenyl) 5-methyl 1,3-dioxane from isoeugenol via the Prins reaction.
Delmas, Michel; Kalck, Phillipe; Gorrichon, Jean-Pierre; Gaset, A. J. Chem. Educ. 1982, 59, 700.
Synthesis |
Catalysis |
Natural Products
The synthesis of 2-acetyl-1,4-naphthoquinone: A multi-step synthesis  Green, Ivan R.
Synthesis of the title compound is carried out through two different pathways that are then compared for their relative merits.
Green, Ivan R. J. Chem. Educ. 1982, 59, 698.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
Synthesis, characterization, and use of a cobalt(II) complex as an NMR shift reagent: An integrated laboratory experiment  Goff, Harold M.; Hines, Jody; Griesel, Jean; Mossman, Craig
Co(AcAc)2(H2O)2 is prepared, isoltated, characterized, and employed as an NMR shift reagent to simplify the spectrum of a complex alcohol.
Goff, Harold M.; Hines, Jody; Griesel, Jean; Mossman, Craig J. Chem. Educ. 1982, 59, 422.
NMR Spectroscopy |
Coordination Compounds |
Synthesis
The direct electrochemical synthesis of [(C6H5)3Ph]2[CoCl4]: An example of the use of anodic oxidation in the preparation of metal ion complexes  Oldham, Colin; Tuck, Dennis G.
Uses a 6 V lantern battery and a simple voltmeter / ammeter.
Oldham, Colin; Tuck, Dennis G. J. Chem. Educ. 1982, 59, 420.
Electrochemistry |
Synthesis |
Coordination Compounds |
Oxidation / Reduction
Cobalt(III) ammines-"Werner" complexes: An undergraduate experiment  Greenaway, Anthony M.; Lancashire, Robert J.
Students synthesize dodecaammine--hexol-tetracobalt(III) bromide, the compound associated with Alfred Werner's theory of the octahedral configuration of transition metal ion complexes.
Greenaway, Anthony M.; Lancashire, Robert J. J. Chem. Educ. 1982, 59, 419.
Coordination Compounds |
Synthesis |
Molecular Properties / Structure
The l9th century purity of American chemicals  Paoloni, Leonello
The synthesis of 1,3,5-triazine was first reported in 1954.
Paoloni, Leonello J. Chem. Educ. 1982, 59, 394.
Synthesis
The problem of syn- versus anti-addition: An organic chemistry laboratory experiment  Silversmith, Ernest F.
An experiment that allows a student to determine whether an addition to a carbon-carbon double bond proceeds in syn- or anti-fashion.
Silversmith, Ernest F. J. Chem. Educ. 1982, 59, 346.
Addition Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Alkenes
Stepwise metathesis: A promising strategy in organic synthesis  Mehta, Goverdhan
An article to stimulate interest in metathetical approaches to diverse organic molecules and highlight recent achievements in this area.
Mehta, Goverdhan J. Chem. Educ. 1982, 59, 313.
Mechanisms of Reactions |
Molecular Properties / Structure |
Synthesis |
Catalysis
The preparation of lucigenin: An experiment with charm  Amiet, R. G.
The preparation of lucigenin involves both nucleophilic and electrophilic aromatic substitution, nucleophilic aliphatic substitution, reductive coupling, and oxidation reactions.
Amiet, R. G. J. Chem. Educ. 1982, 59, 163.
Synthesis |
Oxidation / Reduction |
Nucleophilic Substitution |
Aromatic Compounds
My cooperative work experience at SKF Laboratories  Knipmeyer, Laura L.
One student's experience working cooperatively with chemists to find practical synthetic routes to biologically active compounds that may show promise as drugs.
Knipmeyer, Laura L. J. Chem. Educ. 1982, 59, 45.
Student / Career Counseling |
Synthesis |
Drugs / Pharmaceuticals
Synthesis of tetraphenylporphin: A convenient undergraduate organic laboratory experiment  Bozak, Richard E.; Hill, Craig L.
Procedure for the synthesis of tetraphenylporphin from pyrrole and benzaldehyde.
Bozak, Richard E.; Hill, Craig L. J. Chem. Educ. 1982, 59, 36.
Synthesis |
Dyes / Pigments
Carbanions in organic synthesis (Stowell, John C.)  Bank, Shelton

Bank, Shelton J. Chem. Educ. 1981, 58, A68.
Synthesis
Block and graft copolymers  McGrath, J. E.
Block copolymers; transitional behavior; block copolymer architecture; synthesis; living polymerization sequential addition processes; interaction of functionality terminated oligomers; polymer growth from oligomer end groups; graft copolymers.
McGrath, J. E. J. Chem. Educ. 1981, 58, 914.
Synthesis |
Addition Reactions |
Polymerization
Step-growth polymerization  Stille, J. K.
In step-growth polymerization, the molecular weight of the polymer chain builds up slowly and there is only one reaction mechanism for the formation of polymer. The distinct initiation, propagation, and termination steps of chain-growth polymerization are meaningless in step-growth polymerization.
Stille, J. K. J. Chem. Educ. 1981, 58, 862.
Polymerization |
Reactions |
Mechanisms of Reactions |
Synthesis
Chain reaction polymerization  McGrath, James E.
The purpose of this paper is to attempt to present a reasonable, concise, but up-to-date overview of chain reaction polymerization. The article refers to many excellent papers and books on the subject.
McGrath, James E. J. Chem. Educ. 1981, 58, 844.
Polymerization |
MO Theory |
Synthesis |
Kinetics |
Mechanisms of Reactions
How hazardous is synthetic chemistry?   Quickenden, Terry I.
The purpose of this article is to emphasize the serious need for quantitative occupational-medical studies of the amounts of working material ingested by synthetic chemists in a variety of laboratory situations.
Quickenden, Terry I. J. Chem. Educ. 1981, 58, 503.
Toxicology |
Synthesis
Synthetic materials in art conservation  Werner, Anthony
The purpose of this article is to demonstrate how the chemist working in museums with conservators has succeeded in developing new techniques for the conservation of antiques and works of art.
Werner, Anthony J. Chem. Educ. 1981, 58, 321.
Synthesis |
Plant Chemistry |
Applications of Chemistry
Sir William Henry Perkin, pioneer in color   Nagel, Miriam C.
Perkin discovered synthetic dye (mauve) at the age of 18 and ushered in a entirely new branch of research.
Nagel, Miriam C. J. Chem. Educ. 1981, 58, 305.
Dyes / Pigments |
Applications of Chemistry |
Synthesis
p-Chlorophenoxyacetic acid-preparation of a synthetic plant hormone  Wood, William F.
Instructions for the preparation of a synthetic plant hormone.
Wood, William F. J. Chem. Educ. 1981, 58, 76.
Plant Chemistry |
Hormones |
Synthesis |
Natural Products |
Bioorganic Chemistry
Evolution of a process: The manufacture of diphenyl oxide  Fravel, Harold G., Jr.
An understanding of the chemistry involved in this reaction provides the basis for converting an unprofitable process and plant to a profitable business without a substantial use of capital or a major change in operating procedures.
Fravel, Harold G., Jr. J. Chem. Educ. 1980, 57, 873.
Industrial Chemistry |
Aromatic Compounds |
Synthesis
Computer-assisted teaching of organic synthesis  Stolow, Robert D.; Joncas, Leo J.
12.
Stolow, Robert D.; Joncas, Leo J. J. Chem. Educ. 1980, 57, 868.
Synthesis
Electronic transitions as a probe of tetrahedral versus octahedral coordination in nickel(II) complexes: An undergraduate inorganic chemistry experiment  Filgueiras, Carlos A. L.; Carazza, Fernando
Preparation of a tetrahedral nickel(II) complex and its transformation into an octahedral species, followed by a discussion of spectral results.
Filgueiras, Carlos A. L.; Carazza, Fernando J. Chem. Educ. 1980, 57, 826.
Coordination Compounds |
Crystal Field / Ligand Field Theory |
Synthesis
Preparation and properties of sufatotris(thiourea)zinc(II)  Udupa, M. R.
Preparation and IR analysis of sufatotris(thiourea)zinc(II).
Udupa, M. R. J. Chem. Educ. 1980, 57, 825.
Synthesis |
Coordination Compounds |
IR Spectroscopy
An Ether Synthesis Using Phase Transfer Catalysis  Hill, John W.; Corredor, Jorge
Williamson syntheses may be carried out under milder conditions by employing phase-transfer catalyst; anhydrous solvents are nor needed.
Hill, John W.; Corredor, Jorge J. Chem. Educ. 1980, 57, 822.
Ethers |
Synthesis |
Catalysis
Speeding up the inorganic lab: How fast is too fast?  Sharrock, Patrick
Hydrogen peroxide can be used for speeding up the preparation of cobalt(III) complexes if the solutions are heated to complete the reaction.
Sharrock, Patrick J. Chem. Educ. 1980, 57, 778.
Synthesis
Systematic inorganic reaction chemistry: Inorganic reaction types, general methods of synthesis, and the periodic table  Basolo, Fred
It is possible to teach inorganic reactions and syntheses without students having to memorize specific reactions and without the lectures being dull.
Basolo, Fred J. Chem. Educ. 1980, 57, 761.
Reactions |
Synthesis |
Periodicity / Periodic Table |
Descriptive Chemistry
Preparation of 1,1-Diphenyl-1-hydroxy-3-butanone  Rivett, D. E. A.
Exemplifies the use of a protecting group in organic synthesis.
Rivett, D. E. A. J. Chem. Educ. 1980, 57, 751.
Synthesis |
Molecular Properties / Structure |
Aldehydes / Ketones
The synthesis and proton NMR spectrum of methyl 7-cycloheptatrienylacetate: An advanced undergraduate laboratory experiment  Jurch, G. R., Jr.; Johnston, M. D., Jr.; Perry, J. W.; Detty, T. E.
Gives students an opportunity to apply several synthetic and purification techniques and then provides several opportunities for the application of NMR spectroscopy, including experiments in spin coupling and shift reagents.
Jurch, G. R., Jr.; Johnston, M. D., Jr.; Perry, J. W.; Detty, T. E. J. Chem. Educ. 1980, 57, 743.
Synthesis |
NMR Spectroscopy
Modifications in the synthesis of caprolactam and nylon 6  Malmin, Jon E.
Suggested modifications to the referenced procedure.
Malmin, Jon E. J. Chem. Educ. 1980, 57, 742.
Polymerization |
Synthesis
Synthesis and decomposition of ZnI2  Walker, Noojin
Illustrates direct combination, decomposition, the effect of a catalyst, recrystallization of sublimed I2, and electrolysis.
Walker, Noojin J. Chem. Educ. 1980, 57, 738.
Synthesis |
Reactions |
Catalysis |
Electrochemistry
Simple enols: How rare are they?  Hart, Harold; Sasaoka, Michio
Enols may be synthesized independently of their more stable, keto tautomers; enols are not inherently unstable.
Hart, Harold; Sasaoka, Michio J. Chem. Educ. 1980, 57, 685.
Alcohols |
Synthesis |
Molecular Properties / Structure |
Aldehydes / Ketones |
Phenols
Co(acac)3 Synthesis, reactions, and spectra: An experiment for general chemistry  Shalhoub, George M.
Students demonstrate that nitration of Co(acac)3 has occurred through proton NMR and IR spectroscopy.
Shalhoub, George M. J. Chem. Educ. 1980, 57, 525.
Synthesis |
Spectroscopy |
Titration / Volumetric Analysis |
NMR Spectroscopy |
IR Spectroscopy
The disproportionation of an unsymmetrical azine. An NMR experiment for the undergraduate organic laboratory  Kenny, David H.
Calculating an equilibrium constant using data from an NMR spectrum.
Kenny, David H. J. Chem. Educ. 1980, 57, 462.
NMR Spectroscopy |
Synthesis |
Equilibrium
Synthesis and electrochemistry of cyclopentadienylcarbonyliron tetramer: An advanced experiment  White, A. J.; Cunningham, Alice J.
An advanced-level experiment in which a transition metal cluster compound, cyclopentadienylcarbonyliron tetramer, is synthesized and characterized spectroscopically.
White, A. J.; Cunningham, Alice J. J. Chem. Educ. 1980, 57, 317.
Synthesis |
Electrochemistry |
Metals |
Coordination Compounds |
Transition Elements
Cortisone: The quest for oxygen at C-11  Hazen, George G.
History of the synthesis of cortisone focussing on the placement of oxygen at position 11 in the molecule.
Hazen, George G. J. Chem. Educ. 1980, 57, 291.
Industrial Chemistry |
Applications of Chemistry |
Synthesis |
Molecular Properties / Structure
Chemistry and artists' colors. Part III. Preparation and properties of artists' pigments  Orna, Mary Virginia
Properties and classification of artists' pigments, and procedures for the preparation of chrome yellow, Prussian blue, and thalo blue.
Orna, Mary Virginia J. Chem. Educ. 1980, 57, 267.
Dyes / Pigments |
Applications of Chemistry |
Synthesis
Tetraoxaquaterene Synthesis  Glidewell, Christopher
Application of the referenced experiment to an inorganic setting.
Glidewell, Christopher J. Chem. Educ. 1980, 57, 236.
Synthesis |
Coordination Compounds
An undergraduate organic laboratory project involving independent synthesis of novel flavones  Letcher, R. M.
each student is provided different starting materials to produce different flavones, many of which have not been described in the literature.
Letcher, R. M. J. Chem. Educ. 1980, 57, 220.
Synthesis |
Aromatic Compounds
Patterns in organometallic chemistry with application in organic synthesis  Schwartz, Jeffrey; Labinger, Jay A.
Electron configuration in organo-transition metal complexes, the formation of carbon-metal sigma-bonded species, and the chemistry of metal pi complex compounds.
Schwartz, Jeffrey; Labinger, Jay A. J. Chem. Educ. 1980, 57, 170.
Synthesis |
Organometallics |
Catalysis |
Metals |
Stoichiometry
Organosilicon chemistry: Part I  West, Robert; Barton, Thomas J.
A brief outline or organosilicon chemistry, including the synthesis of organosilanes, chemical bonding in silicon compounds, silicone polymers, and catenated polysilanes.
West, Robert; Barton, Thomas J. J. Chem. Educ. 1980, 57, 165.
Synthesis
The preparation of p-cresyl propyl ether by phase transfer catalysis  Rowe, Jeffrey E.
Modifying the referenced procedure to produce aromatics ethers.
Rowe, Jeffrey E. J. Chem. Educ. 1980, 57, 162.
Catalysis |
Synthesis |
Aromatic Compounds |
Ethers
Diphenylbutadienes syntheses by means of the Wittig reaction: Experimental introduction to the use of phase transfer catalysis  Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L.
Intended as a project carried out by students at the end of introductory organic chemistry.
Gillois, J.; Guillerm, G.; Stephen, E.; Vo-Quang, L. J. Chem. Educ. 1980, 57, 161.
Synthesis |
Catalysis |
Alkenes |
Aldehydes / Ketones |
Stereochemistry
Two for the price of one  Wittcoff, Harold
Several important commercial examples of making two chemicals in one process.
Wittcoff, Harold J. Chem. Educ. 1979, 56, 810.
Industrial Chemistry |
Synthesis
Aspirin and Prostaglandin Synthesis  Harrison, Ernest A., Jr.
Aspirin inhibits the synthesis of prostaglandins.
Harrison, Ernest A., Jr. J. Chem. Educ. 1979, 56, 768.
Synthesis |
Medicinal Chemistry |
Drugs / Pharmaceuticals
Glutamic acid in pheromone synthesis: A useful chiral synthon  Smith, Leverett R.; Williams, Howard J.
Outlines synthetic routes for the formation of various pheromones from glutamic acid.
Smith, Leverett R.; Williams, Howard J. J. Chem. Educ. 1979, 56, 696.
Synthesis |
Chirality / Optical Activity |
Natural Products |
Stereochemistry |
Enantiomers |
Amino Acids
The romance of HMDA  Wittcoff, Harold
The chemistry of hexamethylenediamine.
Wittcoff, Harold J. Chem. Educ. 1979, 56, 654.
Industrial Chemistry |
Synthesis |
Mechanisms of Reactions
Allowed and forbidden d-d transitions in Cr(oxalate)33-  Yager, T. D.; Eaton, G. R.
The synthesis of K3Cr(oxalate)3.3H2O.
Yager, T. D.; Eaton, G. R. J. Chem. Educ. 1979, 56, 635.
Synthesis
A photochemical preparation of indoles: An organic chemistry experiment  Kane, Victoria; Schultz, Arthur G.
Modification of a research-oriented photochemical experiment the provides an early exposure to the synthetic advantages of organic photochemistry and illustrates the formation of a mechanistically interesting carbon-carbon bond.
Kane, Victoria; Schultz, Arthur G. J. Chem. Educ. 1979, 56, 555.
Synthesis |
Photochemistry
A topical alkene preparation and oxidation  Mitchell, Reginald H.; Hawkins, Blaine F.; West, Paul R.
Thermally depolymerizing polystyrene to styrene followed by an investigation of the properties of the flammable monomer produced.
Mitchell, Reginald H.; Hawkins, Blaine F.; West, Paul R. J. Chem. Educ. 1979, 56, 526.
Alkenes |
Synthesis |
Polymerization
Preparation of acetanilide from nitrobenzene  Reeve, Wilkins; Lowe, Valerie C.
An improved synthesis of acetanilide from nitrobenzene that can be completed in a single laboratory period.
Reeve, Wilkins; Lowe, Valerie C. J. Chem. Educ. 1979, 56, 488.
Synthesis
High pressure synthesis of transition metal carbonyls  Hagen, A. P.; Miller, T. S.; Terrell, D. L.; Hutchinson, B.; Hance, R. L.; Daniels, L.
In this procedure carbon monoxide serves as the ligand as well as the reducing agent.
Hagen, A. P.; Miller, T. S.; Terrell, D. L.; Hutchinson, B.; Hance, R. L.; Daniels, L. J. Chem. Educ. 1979, 56, 479.
Synthesis |
Transition Elements |
Metals
A more convenient method of preparation of amide derivatives of carboxylic acids  Long, Karen P.
An adaptation of this method was devised for use in a qualitative organic analysis program.
Long, Karen P. J. Chem. Educ. 1979, 56, 420.
Synthesis |
Amides |
Carboxylic Acids |
Qualitative Analysis |
Catalysis
Synthesis of some unreported derivatives of sulfonamides: A laboratory in organic chemistry  Gilow, Helmuth
Preparation of N4-benzylsulfanilamide.
Gilow, Helmuth J. Chem. Educ. 1979, 56, 419.
Synthesis |
Amides |
Aromatic Compounds
The last (?) word on student preparation of benzalacetophenone  Ellern, James B.
A procedure the rapidly produces a satisfactory yield of benzalacetophenone.
Ellern, James B. J. Chem. Educ. 1979, 56, 418.
Synthesis |
Aldehydes / Ketones
Purification by sub-zero temperature washing  Chu, Samuel S.-T.
Separating an ester from the carboxylic acid from which it was synthesized.
Chu, Samuel S.-T. J. Chem. Educ. 1979, 56, 384.
Synthesis |
Esters |
Carboxylic Acids |
Laboratory Management
Preparation and rearrangement of 2,3-Diphenyl-2,3-butanediol  Markgraf, J. Hodge; Newton, Thomas A.
The title reactions provide a convenient system for demonstrating migratory aptitudes.
Markgraf, J. Hodge; Newton, Thomas A. J. Chem. Educ. 1979, 56, 344.
Synthesis
The synthesis of heterocyclic compounds: Some laboratory experiments  Wolthuis, Enno
A review of the literature on the synthesis of heterocycles revealed several that produced significant yields and could be modified for the organic laboratory.
Wolthuis, Enno J. Chem. Educ. 1979, 56, 343.
Synthesis |
Heterocycles
"Crown ether" synthesis: An organic laboratory experiment  Field, Kurt W.; Glover, A. Donald; Moroz, Judith S.; Collander, Deborah J.; Kolb, Kenneth E.
The starting materials are readily available and the product, a cyclic polyether, belongs to a class of compounds that has aroused interest in both chemists and biologists.
Field, Kurt W.; Glover, A. Donald; Moroz, Judith S.; Collander, Deborah J.; Kolb, Kenneth E. J. Chem. Educ. 1979, 56, 269.
Ethers |
Synthesis
Aqueous chromic acid oxidation of secondary alcohols in diethyl ether: A convenient undergraduate organic chemistry experiment  Thompson, Kerry L.; Krishnamurthy, S.; Nylund, Thomas; Ravindranathan, M.
A two-phase procedure for the oxidation of secondary alcohols to ketones that is applicable to a wide variety of substrates.
Thompson, Kerry L.; Krishnamurthy, S.; Nylund, Thomas; Ravindranathan, M. J. Chem. Educ. 1979, 56, 203.
Aqueous Solution Chemistry |
Oxidation / Reduction |
Alcohols |
Ethers |
Synthesis |
Aldehydes / Ketones
Wohler's synthesis of artificial urea: A modern version of a classic experiment  Chooljian, Steven H.; Kauffman, George B.
History of Wohler's synthesis of artificial urea and an experiment to duplicate that work.
Chooljian, Steven H.; Kauffman, George B. J. Chem. Educ. 1979, 56, 197.
Synthesis
Isopolyvanadates: Synthesis and characterization  Long, G. G.; Stanfield, R. L.; Hentz, F. C., Jr.
Isopolyanions are often neglected and seldom illustrated although they are the predominant feature of the chemistry of numerous oxidation states.
Long, G. G.; Stanfield, R. L.; Hentz, F. C., Jr. J. Chem. Educ. 1979, 56, 195.
Synthesis
Amides and hydrazides from amine and hydrazine hydrochlorides  Shama, Sami A.; Tran, Thuran L.
The Schotten-Baumann procedure is extensively used for the preparation of carboxylic acid derivatives in the undergraduate chemistry laboratory.
Shama, Sami A.; Tran, Thuran L. J. Chem. Educ. 1978, 55, 816.
Amines / Ammonium Compounds |
Carboxylic Acids |
Synthesis
A synthesis of o-chlorocinnamic acid utilizing a Meerwein reaction. An undergraduate organic experiment  Cleland, George H.
The authors share an experimental procedure that converts an o-chloroaniline to o-chlorocinnamic acid.
Cleland, George H. J. Chem. Educ. 1978, 55, 814.
Carboxylic Acids |
Synthesis
A new synthesis of tertiary alkyl N-aryl-carbamates from isocyanates  Bailey, William J.; Griffith, James R.
A simple, convenient, and fast procedure has been developed for the synthesis of tertiary alkyl N-acrylcarbamate from phenyl and 1-naphthyl isocyanates as solid derivatives of tertiary alcohols by the use of lithium tertiary alkoxides as catalysts.
Bailey, William J.; Griffith, James R. J. Chem. Educ. 1978, 55, 809.
Catalysis |
Alcohols |
Synthesis
Microbial conversion of d-sorbitol to l-sorbose. An interdisciplinary experiment illustrating an industrial process  Volker, Eugene J.; Schultz, Clyde
A procedure for an interdisciplinary experiment illustrating an industrial process.
Volker, Eugene J.; Schultz, Clyde J. Chem. Educ. 1978, 55, 673.
Industrial Chemistry |
Chirality / Optical Activity |
Synthesis
Synthesis, characterization, and photogeneration of the 2-methylpyrazinepentacyanoiron(II) complex  Ernhoffer, Robert; Kovacs, Dan; Subak, Edward, Jr.; Shepherd, Rex E.
The authors have incorporated the study of the 2-methylpyrazinepentacyanoiron(II) complex into an upper-division inorganic laboratory course because it is amenable to many characterization techniques.
Ernhoffer, Robert; Kovacs, Dan; Subak, Edward, Jr.; Shepherd, Rex E. J. Chem. Educ. 1978, 55, 610.
Coordination Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Qualitative Analysis
Induced crystallization and reproducibility of preparative reactions  Kucharczyk, N.; Horak, V.
Induced crystallization and reproducibility of preparative reactions.
Kucharczyk, N.; Horak, V. J. Chem. Educ. 1978, 55, 580.
Crystals / Crystallography |
Synthesis |
Laboratory Management
Chemical modification of tung oil. A Diels-Alder experiment for undergraduates  Nitidandhaprabhas, Ovart
This article is a procedure for for an undergraduate experiment designed to illustrate both the Diels-Alder synthesis and the chemical modification of drying oils.
Nitidandhaprabhas, Ovart J. Chem. Educ. 1978, 55, 544.
Lipids |
Synthesis |
Applications of Chemistry
Synthesis of chrysanthemic acid: A multistep organic synthesis for undergraduate students  Schatz, Paul F.
This laboratory is geared toward intermediate organic chemistry laboratory courses that will acquaint students, predominantly chemistry majors, with the strategies and techniques in carrying out a multistep synthesis.
Schatz, Paul F. J. Chem. Educ. 1978, 55, 468.
Synthesis |
Acids / Bases |
Aldehydes / Ketones |
Stereochemistry
Analysis of some synthetic reactions by the HSAB principle  Ho, Tse-Lok
The specificity and efficiency of reactions often have been left unexplained. Addressing these deficiencies, we delineate an empirical analysis of a selected number of synthetic reactions based on the hard and soft acids and bases (HSAB) principle.
Ho, Tse-Lok J. Chem. Educ. 1978, 55, 355.
Acids / Bases |
Synthesis |
Aldehydes / Ketones |
Esters
Synthetic lemon grass oil  Schimelpfenig, C. W.
Instructions for a synthetic lemon grass extraction.
Schimelpfenig, C. W. J. Chem. Educ. 1978, 55, 306.
Synthesis |
Separation Science
Solvay synthesis of sodium hydrogen carbonate. An undergraduate laboratory experiment  Kirksey, H. Graden
There has been little in the undergraduate laboratory literature on the Solvay synthesis. This author shares an activity that can be done with introductory students.
Kirksey, H. Graden J. Chem. Educ. 1978, 55, 272.
Synthesis
Macromolecular solutions as an integral part of beginning physical chemistry  Krause, Sonja
The author discusses macromolecules in solution and to some of the topics from beginning courses in physical chemistry into which this subject should be integrated. The examples given here are not exhaustive, but they can be easily integrated into beginning courses.
Krause, Sonja J. Chem. Educ. 1978, 55, 174.
Solutions / Solvents |
Aqueous Solution Chemistry |
Synthesis |
Biophysical Chemistry |
Molecular Biology
Synthesis and characterization of vinyl pyridine styrene copolymers  Morcellet, M.; Morcellet, J.; Delporte, M.; Estevez, J.
The number of experiments in polymer chemistry are rather limited for undergraduates. This note shares a synthesis and characterization in polymer chemistry.
Morcellet, M.; Morcellet, J.; Delporte, M.; Estevez, J. J. Chem. Educ. 1978, 55, 22.
Synthesis |
Polymerization
Synthesis and properties of an optically active complex: A polarimeter experiment for general chemistry  Hunt, Harold R., Jr.
Synthesizing and determining the optical rotation of d-Co(phen)3(ClO4)3.2H2O.
Hunt, Harold R., Jr. J. Chem. Educ. 1977, 54, 710.
Chirality / Optical Activity |
Molecular Properties / Structure |
Stereochemistry |
Synthesis |
Coordination Compounds
Merocyanin dye preparation for the introductory organic laboratory  Minch, M. J.; Shah, S. Sadiq
Synthesis of a compound that exhibits pronounced color changes with changes in solvent polarity.
Minch, M. J.; Shah, S. Sadiq J. Chem. Educ. 1977, 54, 709.
Dyes / Pigments |
Synthesis
Computer games in chemistry  Smith, Stanley G.; Chabay, Ruth
Describes several chemistry computer games, including one involving organic synthesis.
Smith, Stanley G.; Chabay, Ruth J. Chem. Educ. 1977, 54, 688.
Periodicity / Periodic Table |
Synthesis |
Enrichment / Review Materials
Quarternary ammonia salts: Some recent applications in organic synthesis  Varughese, Pothen
Presents a variety of applications for quarternary ammonia salts, including as reaction media, a reagent for mesylation, catalytic hydrogenation, and micellar and phase-transfer catalysis.
Varughese, Pothen J. Chem. Educ. 1977, 54, 666.
Synthesis |
Amines / Ammonium Compounds |
Micelles |
Catalysis
Phthalimide, anthranilic acid, benzyne. An undergraduate organic laboratory sequence  Dougherty, C. M.; Baumgarten, R. L.; Sweeney, A., Jr.; Concepcion, E.
A synthetic sequence: phthalic anhydride to phthalimide to anthranilic acid to methyl anthranilate or to 1,2,3,4-tetraphenylnaphthalene.
Dougherty, C. M.; Baumgarten, R. L.; Sweeney, A., Jr.; Concepcion, E. J. Chem. Educ. 1977, 54, 643.
Aromatic Compounds |
Mechanisms of Reactions |
Synthesis
Synthesis and characterization of a macrocyclic nickel complex. An experiment to conclude an advanced inorganic or analytical course  Merrell, Philip H.; Urbach, F. L.; Arnold, Michael
The complex 5,7,7,12,14,14-hexamethyl-1,4,8,11-tetraazacyclotetradeca-dieneatonickel(II) iodide is prepared and characterized.
Merrell, Philip H.; Urbach, F. L.; Arnold, Michael J. Chem. Educ. 1977, 54, 580.
Synthesis |
Coordination Compounds |
NMR Spectroscopy |
IR Spectroscopy
Synthesis in an integrated curriculum  Yoder, Claude H.
Outline of a four-year chemistry program culminating in a senior course "Synthesis and Determination of Structure," for which a separate outline is provided.
Yoder, Claude H. J. Chem. Educ. 1977, 54, 572.
Synthesis |
Molecular Properties / Structure
Functionality number. A new focus on an advanced organic chemistry course  Alonso, Miguel E.
A relatively simple method is proposed whereby the reactivity of carbon-containing functional groups is analyzed systematically with emphasis on carbon-carbon bond-forming reactions.
Alonso, Miguel E. J. Chem. Educ. 1977, 54, 568.
Synthesis |
Mechanisms of Reactions
Alkylation of methyl acetoacetate and gas chromatographic analysis of products. An organic laboratory experiment  Schimelpfenig, C. W.
Substituting commercially available sodium methoxide, absolute methanol, and methyl acetoacetate for sodium, ethanol, and acetoacetic ester in the acetoacetic ester synthesis of ketones and acids and the malonic ester synthesis of acids.
Schimelpfenig, C. W. J. Chem. Educ. 1977, 54, 446.
Gas Chromatography |
Chromatography |
Separation Science |
Synthesis |
Esters |
Laboratory Management
Undergraduate kinetics experiment demonstrating unusual behavior of kobs  Malin, John M.; Toma, Henrique E.; Giesbrecht, Ernesto
A reaction in which kobs decreases when the concentration of the excess reactant is increased.
Malin, John M.; Toma, Henrique E.; Giesbrecht, Ernesto J. Chem. Educ. 1977, 54, 385.
Kinetics |
Rate Law |
Synthesis |
Equilibrium
Catalytic dehydrogenation of tetrahydrocarbazole  Van Verth, James E.; Ulmer, Simon W.
The conversion of 1,2,3,4-tetrahydrocarbazole to carbazole illustrates the synthesis of a common heterocyclic system.
Van Verth, James E.; Ulmer, Simon W. J. Chem. Educ. 1977, 54, 383.
Catalysis |
Synthesis |
Aromatic Compounds |
Heterocycles
Benzidine rearrangement and the detection of trace quantities of blood. A laboratory experiment in criminalistics  Pinkus, Jack L.; Goldman, Lyle S.
Synthesis of 3,5,3',5'-tetramethylbenzidine and its application to detect a blood stain.
Pinkus, Jack L.; Goldman, Lyle S. J. Chem. Educ. 1977, 54, 380.
Reactions |
Mechanisms of Reactions |
Forensic Chemistry |
Synthesis |
Applications of Chemistry
One-credit hour undergraduate inorganic laboratory course  Burke, B. A.; Davenport, D. A.; Smith, T. J.; Walton, R. A.
Course structure and and outline of experiments.
Burke, B. A.; Davenport, D. A.; Smith, T. J.; Walton, R. A. J. Chem. Educ. 1977, 54, 360.
Metals |
Transition Elements |
Synthesis |
Oxidation State |
Organometallics |
Coordination Compounds
Copper(II) aspirinate project for the general chemistry laboratory  Dudek, Emily
The weight percent of copper in student-prepared copper(II) aspirinate is measured by electrogravimetric, spectrophotometric, and titrimetric methods.
Dudek, Emily J. Chem. Educ. 1977, 54, 329.
Titration / Volumetric Analysis |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Synthesis |
Quantitative Analysis
Sodium perborate oxidation of an aromatic amine  Huestis, Laurence
Upon learning that the mechanism and even the nature of the oxidizing species is unknown, this reaction assumes new significance and provides an excellent opportunity for speculation on the nature of the reaction and a review of factors that affect the yield.
Huestis, Laurence J. Chem. Educ. 1977, 54, 327.
Aromatic Compounds |
Amines / Ammonium Compounds |
Oxidation / Reduction |
Synthesis |
Mechanisms of Reactions
Synthesis of o-acetylbenzoic acid. An experiment for an honors organic laboratory course  Newman, Melvin S.
An inquiry lab whose purpose is to develop methods to increase the yield of product.
Newman, Melvin S. J. Chem. Educ. 1977, 54, 191.
Synthesis
Juglone: A comparison of natural and synthetic products  Wilbur, James M.; Sublett, Kerry Lyn
Isolating juglone from black walnut hulls and comparing it to synthetic material through melting point and thin layer chromatography.
Wilbur, James M.; Sublett, Kerry Lyn J. Chem. Educ. 1977, 54, 156.
Natural Products |
Synthesis |
Thin Layer Chromatography
The Synthesis and Analysis of Water  Jensen, William B.
Illustrations of Macquer's synthesis and Lavoisier's decomposition of water.
Jensen, William B. J. Chem. Educ. 1977, 54, 142.
Water / Water Chemistry |
Synthesis
The preparation and characterization of a sodium tungsten bronze. An inorganic experiment  Conroy, Lawrence E.
An experiment comprising the synthesis, analysis, and characterization of sodium tungsten bronze.
Conroy, Lawrence E. J. Chem. Educ. 1977, 54, 45.
Solid State Chemistry |
X-ray Crystallography |
Synthesis
Simple apparatus for working with water-sensitive compounds  Bernstein, Stanley C.
This report describes the synthesis of a typical deliquescent substance, tri-n-butylamine hydrochloride, in the absence of air, using standard undergraduate laboratory kit apparatus and a few stopcocks.
Bernstein, Stanley C. J. Chem. Educ. 1976, 53, 694.
Synthesis |
Laboratory Equipment / Apparatus |
Amines / Ammonium Compounds
Student synthesis of tris(ethylenediamine)cobalt(III) chloride  Krause, Ronald A.; Megargle, Elizabeth A.
The authors have developed a more rapid synthesis of tris(ethylenedianime) cobalt (III) chloride than the customary approach; this experiment is quite suitable for inclusion in an undergraduate laboratory.
Krause, Ronald A.; Megargle, Elizabeth A. J. Chem. Educ. 1976, 53, 667.
Coordination Compounds |
Synthesis
Crown ethers. A new aid to synthesis and to elucidation of reaction mechanisms  Knipe, A. C.
Although there have been many recent and exciting developments in the synthesis of these compounds, no attempt will be made in this review, to update a comprehensive catalogue of such achievement. The emphasis will alternatively be on successful application of macrocyclic polyethers within the the title areas.
Knipe, A. C. J. Chem. Educ. 1976, 53, 618.
Mechanisms of Reactions |
Ethers |
Heterocycles |
Synthesis
Molecular design of compounds via intermolecular Diels-Alder reactions  Mehta, Goverdhan
The Diels-Alder reaction involving a cycloaddition between a diene and dienophile is one of the most versatile and useful reactions in the armory of the synthetic organic chemists.
Mehta, Goverdhan J. Chem. Educ. 1976, 53, 551.
Synthesis |
Addition Reactions |
Aromatic Compounds
Preparation of the sweetening agent P4000. A student project  de Koning, A. J.
The author presents the procedure for preparation of the sweetening agent P4000 that can be performed by students.
de Koning, A. J. J. Chem. Educ. 1976, 53, 521.
Synthesis |
Food Science |
Carbocations |
Aromatic Compounds
The scope of the Haworth synthesis  Agranat, Israel; Shih, Yu-Shan
The duality of the Haworth synthesis as revealed most conspicuously in the preparation of both anthracene and phenanthrene, widens the scope of the method. On the basis of the reversibility of Friedel-Crafts acylation in PPA, the Haworth synthesis may serve as a route to linearly annelated-as well as to angularly annelated polynuclear aromatic hydrocarbons.
Agranat, Israel; Shih, Yu-Shan J. Chem. Educ. 1976, 53, 488.
Synthesis |
Catalysis |
Aromatic Compounds |
Aldehydes / Ketones
Grignard dehydration reactions. An undergraduate organic experiment.  Duty, Robert C.; Ryder, Bernard L.
In this laboratory, the authors have incorporated the Grignard reaction in a step-wise synthesis that has been successful in demonstrating several experimental and instrumental techniques.
Duty, Robert C.; Ryder, Bernard L. J. Chem. Educ. 1976, 53, 457.
Grignard Reagents |
Reactions |
Synthesis |
Alkenes
Determining the Kp for the ammonia synthesis as a function of temperature  Huybrechts, G.; Petre, G.
This paper describes a short physical chemistry experiment which has been used successfully for several years in the authors' laboratories. The experiment enables an undergraduate student to determine the equilibrium constant for the "classic" ammonia-synthesis reaction as a function of temperature and to calculate the corresponding heat of reaction and entropy change.
Huybrechts, G.; Petre, G. J. Chem. Educ. 1976, 53, 443.
Synthesis |
Equilibrium |
Thermodynamics
Speeding-up the preparation of coordination compounds in undergraduate laboratory classes  Leverett, Peter; Oliver, Mervyn J.
The author describe steps that can be taken to cut down the time it takes to prepare coordination compounds.
Leverett, Peter; Oliver, Mervyn J. J. Chem. Educ. 1976, 53, 440.
Coordination Compounds |
Laboratory Management |
Synthesis
Structural assignment of a C10H12O3 ester by mass spectroscopy. An undergraduate organic problem  Marchand, Alan P.; Jackson, Danny
The authors provide challenging problems to help students integrate spectroscopic methods.
Marchand, Alan P.; Jackson, Danny J. Chem. Educ. 1976, 53, 390.
Spectroscopy |
Synthesis |
Esters |
Mass Spectrometry
Dimethylaminodifluorophosphine - Preparation and NMR spectra  Dobbie, R. C.
Instructions for the preparation and analysis of dimethylaminodifluorophosphine.
Dobbie, R. C. J. Chem. Educ. 1976, 53, 129.
NMR Spectroscopy |
Synthesis
Computer assisted instruction in organic synthesis  Feldman, Martin; Bishop, Marvin
The authors have used two successful Basic programs where students had practice with a series of interconversions involving alphatic and aromatic compounds.
Feldman, Martin; Bishop, Marvin J. Chem. Educ. 1976, 53, 91.
Aromatic Compounds |
Synthesis
a[alpha]- and [bet]a-D-glucose pentaacetate. An experiment in structure assignment using NMR  Pearson, Wesley A.; Spessard, Gary O.
The synthesis and structural determination of alpha- and beta-D-glucose pentaacetate.
Pearson, Wesley A.; Spessard, Gary O. J. Chem. Educ. 1975, 52, 814.
NMR Spectroscopy |
Carbohydrates |
Synthesis
The preparation and photochemistry of stilbenes. A synthetic organic chemistry experiment  Davy, J. R.; Jessup, P. J.; Reiss, J. A.
The synthesis of 3,6-dimethylphenanthrene.
Davy, J. R.; Jessup, P. J.; Reiss, J. A. J. Chem. Educ. 1975, 52, 747.
Photochemistry |
Aromatic Compounds |
Synthesis
Out-of-plane metalloporphyrin complexes  Taylor, Glenn A.; Tsutsui, Minoru
Considers the synthesis and structure of metalloporphyrins.
Taylor, Glenn A.; Tsutsui, Minoru J. Chem. Educ. 1975, 52, 715.
Organometallics |
Coordination Compounds |
Synthesis |
Molecular Properties / Structure
A case history of unplanned development of new chemistry  Roberts, John D.
Work to synthesize a cyclobutadiene derivative resulted in an unanticipated procedure.
Roberts, John D. J. Chem. Educ. 1975, 52, 708.
Alkenes |
Synthesis |
Aldehydes / Ketones
Solid phase synthesis  Neckers, D. C.
Describes the process of solid phase synthesis and its applications in polypeptide synthesis and immobilized enzymes and catalysts.
Neckers, D. C. J. Chem. Educ. 1975, 52, 695.
Synthesis |
Proteins / Peptides |
Enzymes |
Catalysis
A biologically based evaluation of sulfanilamide purity: A biological extension of a standard organic sequential synthesis  Nelson, George L.; Buongiorno, Paul A.
An experiment designed to compare the biological activities of synthesized sulfanilamide to that of reagent grade material.
Nelson, George L.; Buongiorno, Paul A. J. Chem. Educ. 1975, 52, 676.
Synthesis |
Drugs / Pharmaceuticals |
Applications of Chemistry
The Gabriel synthesis of benzylamine: An undergraduate organic experiment  Nigh, W. G.
The Gabriel synthesis involves the reaction of the conjugate base of phthalimide and an alkyl halide to give an alkyl phthalimide which is subsequently hydrolyzed to the primary alkyl amine; the reaction is important historically for the synthesis of pure primary amines uncontaminated by secondary or tertiary by-products.
Nigh, W. G. J. Chem. Educ. 1975, 52, 670.
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
The hypothetical synthesis of adrenaline: The preparation and properties of amines  Schambach, Robert A.
Using an examination of several hypothetical ways to synthesize adrenaline as the basis of a lecture on the preparation and properties of amines.
Schambach, Robert A. J. Chem. Educ. 1975, 52, 654.
Synthesis |
Amines / Ammonium Compounds
Synthesis and structure of magnesium oxide or calcium oxide. An integrated inorganic-physical experiment  Moyer, Ralph O.
The objectives of this experiment are to demonstrate that binary oxides can be prepared by thermal decomposition of oxy compounds such as oxalates and to introduce elementary x-ray crystallography and its application to the determination of structure.
Moyer, Ralph O. J. Chem. Educ. 1975, 52, 612.
Synthesis |
X-ray Crystallography |
Crystals / Crystallography
Fading of bromophenol blue. A combined synthesis and spectrophotometric kinetics experiment  Winans, Randall; Brown, Charles Allan
An experimental sequence involving the synthesis of phenosulfonphthalein, bromination of this to give bromophenol blue, and study of the fading of the latter in a strongly alkaline medium.
Winans, Randall; Brown, Charles Allan J. Chem. Educ. 1975, 52, 526.
Dyes / Pigments |
Synthesis |
Kinetics |
Spectroscopy |
Quantitative Analysis
ClF6+  Friesen, R. J.
The synthesis of the hexafluorochlorine ion. Reported in Inorganic Chemistry, 12 (7), 1580 (1973).
Friesen, R. J. J. Chem. Educ. 1975, 52, 521.
Synthesis
The appreciation of molecular transformation in organic chemistry. Part II: Two ingenious syntheses  Ranganathan, S.; Ranganathan, D.
Step-by-step analysis of an involved organic transformation.
Ranganathan, S.; Ranganathan, D. J. Chem. Educ. 1975, 52, 493.
Synthesis
Computer-assisted instruction in organic synthesis  Orf, H. W.
Computer-assisted instruction in organic synthesis using a program called LHASA.
Orf, H. W. J. Chem. Educ. 1975, 52, 464.
Synthesis
Concerning the synthesis of phencyclone (1,3-diphenyl-2-cyclopenta[l]phenanthrene-2-one)  Harrison, Ernest A., Jr.; Grove, William S.
The referenced synthesis presents some serious drawbacks.
Harrison, Ernest A., Jr.; Grove, William S. J. Chem. Educ. 1975, 52, 461.
Synthesis
The origin of the Birch reduction  Birch, A. J.
In 1940 the RAF was led to believe that German fighter pilots were being given cortical hormones or biologically active substitutes and wanted some of their own.
Birch, A. J. J. Chem. Educ. 1975, 52, 458.
Synthesis |
Natural Products |
Hormones
Benzylthiuronium bicarbonate for the derivatization of carboxylic acids  Reddy, J. V. Krishna; Bopari, K. S.
Preparing benzylithiuronium carboxylates with benzylithiuronium bicarbonate.
Reddy, J. V. Krishna; Bopari, K. S. J. Chem. Educ. 1975, 52, 324.
Carboxylic Acids |
Synthesis
Organometallic catalyzed synthesis and characterization of polyethylene. An advanced laboratory experiment  Kranbuehl, D. E.; Harris, T. V.; Howe, A. K.; Thompson, D. W.
The Ziegler catalyzed synthesis of linear polyethylene by titanium-aluminum systems and the study of its properties through IR, density, and viscosity measurements.
Kranbuehl, D. E.; Harris, T. V.; Howe, A. K.; Thompson, D. W. J. Chem. Educ. 1975, 52, 261.
Organometallics |
Synthesis |
Catalysis |
Polymerization
A non-hazardous, bench top experiment with an electron-deficient compound  James, B. D.
The synthesis of bis(triphenylphosphine) copper(I) tetrahydroborate.
James, B. D. J. Chem. Educ. 1975, 52, 260.
Synthesis |
Organometallics
The polyhalide experiment and the Open University summer school  Mason, Joan
The problem is to make a polyhalide and identify it by simple quantitative tests.
Mason, Joan J. Chem. Educ. 1975, 52, 244.
Synthesis |
Quantitative Analysis
Synthesis, properties, and hydrolysis of antimony trichloride  Hentz, F. C., Jr.; Long, G. G.
Antimony trichloride is prepared in the same manner as Glauber; a chemical equilibrium that was investigated by LeChatelier is examined; and the antimony in the mercuris vitae of Paracelsus is determined.
Hentz, F. C., Jr.; Long, G. G. J. Chem. Educ. 1975, 52, 189.
Synthesis
Synthesis of sulfuric acid by the contact process. A student laboratory experiment  Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F.
Experimental apparatus and details for the synthesis of sulfuric acid by the contact process.
Martin, J. A.; Baudot, P.; Monal, J. L.; Lejaille, M. F. J. Chem. Educ. 1975, 52, 188.
Synthesis |
Catalysis |
Oxidation / Reduction |
Industrial Chemistry
Organoboranes and organoborate anions. New classes of electrophiles and nucleophiles in organic synthesis  Negishi, Ei-ichi
Presents some of the key features common to various reactions of organoboranes and interprets them in terms of a few common mechanistic schemes.
Negishi, Ei-ichi J. Chem. Educ. 1975, 52, 159.
Synthesis |
Mechanisms of Reactions
Structural determinations in organic chemistry. Synthesis of isomeric allylic alcohols  Arnaud, Christian
The experiment described here represents a two month laboratory study problem for second-year students in the synthesis of isomeric allylic alcohols.
Arnaud, Christian J. Chem. Educ. 1974, 51, 819.
Alcohols |
Synthesis |
Undergraduate Research |
NMR Spectroscopy
A synthesis of amphetamine  Wassink, B. H. Groot; Duijndam, A.; Jansen, A. C. A.
In the course of the authors' educational program in pharmacochemsitry, literature research was performed on the synthesis of amphetamine and pervitin. They share a procedure for these synthesis.
Wassink, B. H. Groot; Duijndam, A.; Jansen, A. C. A. J. Chem. Educ. 1974, 51, 671.
Synthesis |
Drugs / Pharmaceuticals
An interesting and successful organic experiment   Want, Benjamin J-S.
Students are enthusiastic about synthesizing the active ingredient in bug-repelent-OFF.
Want, Benjamin J-S. J. Chem. Educ. 1974, 51, 631.
Synthesis |
Consumer Chemistry
A combined infrared and kinetic study of linkage isomers. An inorganic experiment  Hohman, William H.
In this experiment, the rate of isomerization of the nitrito to the nitro isomer is followed in the solid state using an infrared technique. The order of the reaction and the mechanism for the conversion can be determined.
Hohman, William H. J. Chem. Educ. 1974, 51, 553.
Mechanisms of Reactions |
Synthesis |
Coordination Compounds |
IR Spectroscopy
Synthesis and spectral study of copper(II) complexes  Potts, Richard A.
The authors propose a series of experiments for general chemistry that are related to one and another.
Potts, Richard A. J. Chem. Educ. 1974, 51, 539.
Coordination Compounds |
Synthesis |
Spectroscopy
A photochromic compound: A preparation for the introductory organic laboratory  Ault, Addison; Kouba, Craig
The authors describe a preparation for a photochromic compound for the introductory organic laboratory.
Ault, Addison; Kouba, Craig J. Chem. Educ. 1974, 51, 395.
Photochemistry |
Synthesis
A modified procedure for the preparation of benzalacetophenone  Ventura, Monteserrat
The author reports his modification that benzalacetophenone can be prepared in good yield.
Ventura, Monteserrat J. Chem. Educ. 1974, 51, 353.
Synthesis |
Laboratory Management
The characterization of a coordination complex using infrared spectroscopy: An inorganic or instrumental experiment  Nathan, Lawrence C.
The experiment featured in this article is designed to expose students to synthetic inorganic chemistry, some inorganic applications of infrared spectroscopy, use of infrared instrumentation and various sampling techniques, and use of the chemical literature.
Nathan, Lawrence C. J. Chem. Educ. 1974, 51, 285.
Synthesis |
Spectroscopy |
Quantitative Analysis
Preparation and properties of potassium trioxalatoferrate(III) trihydrate  Aravamudan, G.; Gopalakrishnan, J.; Udupa, M. R.
The authors report on an exercise involving potassium trioxalatoferrate(III) trihydrate as an illustrative exercise in general chemistry laboratory courses.
Aravamudan, G.; Gopalakrishnan, J.; Udupa, M. R. J. Chem. Educ. 1974, 51, 129.
Coordination Compounds |
Synthesis |
Physical Properties
A simulated research project in synthetic organic chemistry: An undergraduate laboratory  Bobbitt, J. M.; Huang, Samuel J.
An undergraduate laboratory of a simulated research project in synthetic organic chemistry.
Bobbitt, J. M.; Huang, Samuel J. J. Chem. Educ. 1974, 51, 58.
Synthesis |
Aromatic Compounds
The use of networks in organic synthesis  Zune, Albert E.; Hollstein, Ulrich
Beginning students in organic chemistry have to overcome seemingly insurmountable tasks. They are learning a myriad of new compounds, physical concepts, reactions, their scope, mechanistic pathways, and many other aspects. Synthesis reactions leave these students at a loss.
Zune, Albert E.; Hollstein, Ulrich J. Chem. Educ. 1974, 51, 16.
Synthesis
Total analysis of tin tetraiodide: A multipurpose experiment  Wheatland, D. A.
Students prepare and purify a sample of tin tetraiodide and then analyze it for iodine and tin using a variety of analytical techniques.
Wheatland, D. A. J. Chem. Educ. 1973, 50, 854.
Titration / Volumetric Analysis |
Synthesis |
Quantitative Analysis
A simple and inexpensive dilution apparatus  Vogtle, Fritz; Wittig, Gunther
A simple and inexpensive setup useful for the synthesis of medium- and larger-ring compounds using the dilution principle.
Vogtle, Fritz; Wittig, Gunther J. Chem. Educ. 1973, 50, 650.
Laboratory Equipment / Apparatus |
Synthesis
An approach to computer-assisted drill in synthetic organic chemistry  Clark, H. A.; Marshall, J. C.; Isenhour, T. L.
This report details an approach to generating computer-assisted exercises in synthetic organic chemistry appropriate for introductory, undergraduate, organic courses.
Clark, H. A.; Marshall, J. C.; Isenhour, T. L. J. Chem. Educ. 1973, 50, 645.
Synthesis
Prostaglandins  Magliulo, Anthony
Reviews the structure, synthesis, metabolism, extraction, separation, quantitation, and biological role of prostaglandins.
Magliulo, Anthony J. Chem. Educ. 1973, 50, 602.
Molecular Properties / Structure |
Synthesis |
Metabolism
The law of definite proportions. An experiment for introductory chemistry  Wilhelm, Dale L.
Using the synthesis of copper iodide to demonstrate the law of definite proportions has advantages over other compounds.
Wilhelm, Dale L. J. Chem. Educ. 1973, 50, 436.
Stoichiometry |
Synthesis
Synthesis of a photochromic benzothiazolinic spiropyran  Guglielmetti, R.; Meyer, R.; Dupuy, C.
The purpose of this type of experiment is to elucidate structure of the different compounds gradually prepared starting from reaction mechanisms and chiefly from spectroscopic data given perviously to students.
Guglielmetti, R.; Meyer, R.; Dupuy, C. J. Chem. Educ. 1973, 50, 413.
Photochemistry |
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure
The origin of the chemical elements, 2  Selbin, Joel
Summarizes the process of nucleosynthesis.
Selbin, Joel J. Chem. Educ. 1973, 50, 380.
Periodicity / Periodic Table |
Astrochemistry |
Nuclear / Radiochemistry |
Synthesis
Synthesis sheets: An aid to synthetic analysis  Still, W. Clark
An instructional tool to assist students in organizing and representing synthetic pathways.
Still, W. Clark J. Chem. Educ. 1973, 50, 378.
Synthesis
The preparation and dehydration of 1-benzylcycloalkanols  Newkome, George R.; Allen, J. W.; Anderson, G. M.
This reaction sequence sheds light on carbocation intermediates, steric effects, conjugation, and elimination mechanisms.
Newkome, George R.; Allen, J. W.; Anderson, G. M. J. Chem. Educ. 1973, 50, 372.
Synthesis |
Alcohols |
Mechanisms of Reactions |
Elimination Reactions
The synthesis and nitration of benzene-d1  Todd, David
The synthesis of labeled benzene-d1 and its conversion to meta-dinitrobenzene.
Todd, David J. Chem. Educ. 1973, 50, 366.
Aromatic Compounds |
Synthesis |
Isotopes |
IR Spectroscopy
Analysis of an important air pollutant: Peroxyacetyl nitrate  Stephens, Edgar R.; Price, Monty A.
Synthesis and IR analysis of peroxyacetyl nitrate (PAN).
Stephens, Edgar R.; Price, Monty A. J. Chem. Educ. 1973, 50, 351.
Atmospheric Chemistry |
Chromatography |
IR Spectroscopy |
Synthesis
Homogeneous catalysis in industrial synthesis. Acetaldehyde, vinyl acetate, and vinyl chloride  Hartley, F. R.
Describes the synthesis of three closely related heavy organic chemicals - acetaldehyde, vinyl acetate, and vinyl chloride - and shows how the synchronous run-down of the coal industry and build-up of the oil industry have necessitated a complete change in the technology required for their preparation.
Hartley, F. R. J. Chem. Educ. 1973, 50, 263.
Catalysis |
Industrial Chemistry |
Synthesis |
Aldehydes / Ketones
An experiment sequence involving potassium trioxalatoferrate(III) trihydrate  Brooks, David W.
This procedure explores the synthesis, analysis, and photochemical reactions of potassium trioxalatoferrate(III) trihydrate.
Brooks, David W. J. Chem. Educ. 1973, 50, 218.
Industrial Chemistry |
Synthesis |
Photochemistry
The ethylene ketal protecting group in organic synthesis. An undergraduate laboratory experiment  Paulson, D. R.; Hartwig, A. L.; Moran, G. F.
This reactive sequence involves the preparation of the ethylene ketal of ethyl acetoacetate using the standard p-toluene-sulfonic acid catalyzed procedure; once the reactive ketone moiety has been masked, the reactive ester group can be modified.
Paulson, D. R.; Hartwig, A. L.; Moran, G. F. J. Chem. Educ. 1973, 50, 216.
Synthesis |
Esters |
Aldehydes / Ketones
The synthesis of fused cycloalkenones via annelation methods  Mundy, Bradford P.
A review of the Robinson annelation reaction, which has been invaluable for syntheses in the terpene and steroid fields.
Mundy, Bradford P. J. Chem. Educ. 1973, 50, 110.
Synthesis |
Aldehydes / Ketones |
Nucleophilic Substitution |
Mechanisms of Reactions
The absorption of light by oriented molecules  Wilson, R. Marshall; Gardner, Edward J.; Squire, Richard H.
Designed to expose students to classical techniques of organic dye synthesis.
Wilson, R. Marshall; Gardner, Edward J.; Squire, Richard H. J. Chem. Educ. 1973, 50, 94.
Photochemistry |
Molecular Properties / Structure |
Dyes / Pigments |
Synthesis
A multidimensional experiment. Synthesis of sulfa drug and its use as a chemotherapeutic agent  Krantz, A.; Jesaitis, R. G.
Students synthesize sulfanilamide or sulfathiazole and independently investigate their effect on bacteria cultures.
Krantz, A.; Jesaitis, R. G. J. Chem. Educ. 1973, 50, 76.
Synthesis |
Drugs / Pharmaceuticals
The preparation and analysis of some metal-pyridine complexes. A general chemistry experiment  Kauffman, George B.; Albers, Richard A.; Harlan, Fred L.
A general chemistry experiment in which students synthesize and then characterize some metal-pyridine complexes.
Kauffman, George B.; Albers, Richard A.; Harlan, Fred L. J. Chem. Educ. 1973, 50, 70.
Coordination Compounds |
Synthesis
Annual reports in synthetic chemistry, 1970 (McMurry, John; Miller, R. Bryan)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1972, 49, A493.
Synthesis |
Reactions
Compendium of organic synthetic methods (Harrison, Ian; Harrison, Shuyen)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1972, 49, A490.
Synthesis
Principles of organic synthesis (Norman R. O. C.)  Cronyn, Marshall W.

Cronyn, Marshall W. J. Chem. Educ. 1972, 49, A434.
Synthesis
Advanced Organic Synthesis: Methods and Techniques (Monson, Richard S.)  MacKay, Francis P.

MacKay, Francis P. J. Chem. Educ. 1972, 49, A397.
Synthesis
Methoden der organischen chemie. Band 5/1C Teil 3. Kohlenwasserstoff. Conjugated dienes, diels-alder reaction (Muller, Eugen)  Richter, G. H.

Richter, G. H. J. Chem. Educ. 1972, 49, A42.
Synthesis
Survey of organic syntheses (Buehler, Calvin A.)  Renfrow, W. B.

Renfrow, W. B. J. Chem. Educ. 1972, 49, A40.
Synthesis
Use of molecular sieves in high vacuum pumping systems  Yuki, Heimei; Hatada, Koichi; Hasegawa, Toshihiko; Kokan, Susumu; Maruo, Katsuhiko
Discusses the method of operation and studies on operating conditions for a sorption pump filled with molecular sieves and applied to a high vacuum system in organic synthesis.
Yuki, Heimei; Hatada, Koichi; Hasegawa, Toshihiko; Kokan, Susumu; Maruo, Katsuhiko J. Chem. Educ. 1972, 49, 849.
Laboratory Equipment / Apparatus |
Laboratory Management |
Synthesis
Furfural - Ubiquitous natural product  McCullough, CSC, Thomas
Procedure for obtaining 2-furaldehyde from citrus peelings, banana skins, gourd rinds, corn cobs, dried leaves, and other organic wastes.
McCullough, CSC, Thomas J. Chem. Educ. 1972, 49, 836.
Natural Products |
Synthesis |
Aldehydes / Ketones
A new method for learning organic reactions  Perlmutter, Howard D.; Kristol, David S.
Using wooden cubes in a game to help students learn organic reactions.
Perlmutter, Howard D.; Kristol, David S. J. Chem. Educ. 1972, 49, 793.
Reactions |
Mechanisms of Reactions |
Synthesis
Transition metal vapors in chemical synthesis. The direct preparation of dibenzene chromium as an undergraduate experiment  Timms, P. L.
A procedure for preparing dibenzene chromium from chromium vapor and benzene.
Timms, P. L. J. Chem. Educ. 1972, 49, 782.
Transition Elements |
Metals |
Synthesis |
Organometallics
Experiencing relevancy in organic chemistry. Hexachlorophene - manufacturing the great clean-all  Moye, Alfred L.
Presents an experiment developed from a term paper by a student who had a serious dislike for organic chemistry.
Moye, Alfred L. J. Chem. Educ. 1972, 49, 770.
Applications of Chemistry |
Consumer Chemistry |
Aromatic Compounds |
Synthesis
N-acetylanthranilic acid. A highly triboluminescent material  Erikson, John
The triboluminescence of N-acetylanthranilic acid adds intrigue to its synthesis.
Erikson, John J. Chem. Educ. 1972, 49, 688.
Acids / Bases |
Photochemistry |
Synthesis
The chemical synthesis of proteins (Solid phase peptide synthesis)  Peck, M. L.; Hruby, V. J.

Peck, M. L.; Hruby, V. J. J. Chem. Educ. 1972, 49, 652.
Proteins / Peptides |
Synthesis
The elusive perbromates  Herrell, A. Y.; Gayer, K. H.
Considers theory on the instability of perbromates, the discovery and method of their synthesis, and their properties.
Herrell, A. Y.; Gayer, K. H. J. Chem. Educ. 1972, 49, 583.
Periodicity / Periodic Table |
Synthesis
Organic chemistry laboratory. A non-traditional approach  Nugent, Maurice J.
A problem-solving approach to the organic chemistry laboratory in which students are asked to identify and then synthesize two unknowns.
Nugent, Maurice J. J. Chem. Educ. 1972, 49, 491.
Synthesis |
Qualitative Analysis
Juglone: An organic chemistry-ecology interaction experiment  Jesaitis, R. G.; Krantz, A.
This procedure involves conversion of 1,5-naphthalenediol to juglone by dichromate oxidation and testing the effect that juglone has on the sprouting behavior of seeds.
Jesaitis, R. G.; Krantz, A. J. Chem. Educ. 1972, 49, 436.
Plant Chemistry |
Synthesis
Organic sulfur compounds in synthesis  Sinclair, Dean L.
Offers generalizations to complement the cited discussion.
Sinclair, Dean L. J. Chem. Educ. 1972, 49, 380.
Synthesis
Carbenes in insertion and addition reactions  Buehler, Calvin A.
Summarizes the reactions typical of insertion and addition.
Buehler, Calvin A. J. Chem. Educ. 1972, 49, 239.
Addition Reactions |
Reactive Intermediates |
Mechanisms of Reactions |
Synthesis
Ferricinium picrate. Preparation of a ferrocene derivative  Johnson, D. W.; Rayner-Canham, G. W.
The preparation and characterization of ferricinium picrate.
Johnson, D. W.; Rayner-Canham, G. W. J. Chem. Educ. 1972, 49, 211.
Synthesis
The preparation of 3-phenylanthranil. A sequential experiment for the undergraduate organic laboratory  Kenny, David H.; Strieter, Jeffrey C.
A sequence of reactions that can be completed by the average student over ten weeks and involves a Friedel-Crafts reaction and Hofmann rearrangement.
Kenny, David H.; Strieter, Jeffrey C. J. Chem. Educ. 1972, 49, 130.
Synthesis |
Reactions
Directive effects in electrophilic aromatic substitution. An organic chemistry experiment  Beishline, Robert R.
The student is given the procedure for the monobromination of acetanilide in glacial acetic acid, but is not told where on the ring the bromine will substitute; he is required to prove the structure of the product through an independent synthesis of the preparation of a known derivative.
Beishline, Robert R. J. Chem. Educ. 1972, 49, 128.
Aromatic Compounds |
Electrophilic Substitution |
Synthesis |
Alkylation
The Ene Synthesis  Keung, Edmund C.; Alper, Howard
Examines developments of an "indirect substitutive addition" or "ene synthesis" reaction.
Keung, Edmund C.; Alper, Howard J. Chem. Educ. 1972, 49, 97.
Synthesis |
Alkenes |
Mechanisms of Reactions |
Reactions
Alkylations in organic chemistry  Mundy, Bradford P.
Examines some of the subtle factors involved in alkylations, including alkylations via enolates, alkylations via enamines, and alkylation of enolates derived from reduction of enone systems.
Mundy, Bradford P. J. Chem. Educ. 1972, 49, 91.
Synthesis |
Alkylation |
Aldehydes / Ketones |
Mechanisms of Reactions
Benzoxazinone synthesis. An organic chemistry experiment  Eckroth, David R.
The preparation of 2-methyl-4H-3,1-benzoxazin-4-one and 2(2'-methanesulfonamido)phenyl-4H-3,1-benzoxazin-4-one exposes students to reactive intermediates.
Eckroth, David R. J. Chem. Educ. 1972, 49, 66.
Synthesis |
Aromatic Compounds |
Reactive Intermediates
Syntheses and Reactions in Organic Chemistry (Parham, William E.)  Paukstelis, Joesph V.

Paukstelis, Joesph V. J. Chem. Educ. 1971, 48, A780.
Synthesis
Preparation and nmr analysis of a silythiocarbamate. An advanced laboratory project  Suydam, Fred H.; Yoder, Claude H.
By a series of reactions, not commonly found in undergraduate texts, the student prepares a silythiocarbamate, determines its structure by use of ir and nmr measurements, and measures certain rotational parameters of the carbon-nitrogen bond by means of variable temperature nmr analysis.
Suydam, Fred H.; Yoder, Claude H. J. Chem. Educ. 1971, 48, 849.
Synthesis |
NMR Spectroscopy |
IR Spectroscopy
Independent synthesis projects in the organic chemistry laboratory  Hiegel, Gene; Belloli, Robert
Students in second semester organic chemistry select a two-step synthesis from the literature, carry out the necessary laboratory work, and then report the results to the class.
Hiegel, Gene; Belloli, Robert J. Chem. Educ. 1971, 48, 825.
Synthesis
Organic sulfur compounds in organic synthesis  Block, Eric
Surveys the many syntheses of organic sulfur compounds.
Block, Eric J. Chem. Educ. 1971, 48, 814.
Synthesis |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
Computer-aided teaching of organic synthesis  Smith, Stanley G.
This article outlines a computer program that can give essentially instantaneous evaluations of students' work on an individual basis.
Smith, Stanley G. J. Chem. Educ. 1971, 48, 727.
Synthesis
Safety hazard from m-toluidine  Trumbull, Elmer R.
The author cautions readers of an experiment that has been used for a long time in organic chemistry.
Trumbull, Elmer R. J. Chem. Educ. 1971, 48, 640.
Synthesis
The preparation and analysis of some double salts. An introductory experiment  Snavely, Fred A.; Yoder, Claude H.
The introduction of analytical techniques into the general chemistry laboratory has too often meant the addition of routine analysis of "unknowns." Chemists are generally more concerned with the identification and characterization of their own preparations, and thus it would seem more desirable to adopt the same approach in the student laboratory.
Snavely, Fred A.; Yoder, Claude H. J. Chem. Educ. 1971, 48, 621.
Synthesis
Preparation of 2,3-diphenyl-1-indenone and related compounds  Clark, Thomas J.
The author describes a series of preparative experiments which students in organic chemistry have found enjoyable and instructive.
Clark, Thomas J. J. Chem. Educ. 1971, 48, 554.
Synthesis |
Aldehydes / Ketones |
Aromatic Compounds
Two syntheses for the organic undergraduate  Vaughn-Williams, H. R.
This article provides the experimental procedure for two syntheses experiments.
Vaughn-Williams, H. R. J. Chem. Educ. 1971, 48, 259.
Synthesis
The preparation and investigation of bis(acetylacetonato)copper(II)  Peacock, Robert D.
In this article the authors share the laboratory script given to students for the preparation and investigation of bis(acetylacetonato)copper(II) along with notes, and followed by a discussion project.
Peacock, Robert D. J. Chem. Educ. 1971, 48, 133.
Synthesis
Reagents for organic synthesis. Volume 2 (Fieser, Mary; Fieser, Louis)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1970, 47, A726.
Synthesis |
Laboratory Management
Organic synthesis (Ireland, Robert E.)  White, J. D.

White, J. D. J. Chem. Educ. 1970, 47, A391.
Synthesis
Cobalt complexes dangerous  Bretherick, L.
Cobalt ammine complexes containing bound oxygen are potentially explosive when subject to shock or high temperatures.
Bretherick, L. J. Chem. Educ. 1970, 47, A204.
Coordination Compounds |
Synthesis
Synthesis and technique in inorganic chemistry (Angelici, Robert J.)  Kauffman, George B.

Kauffman, George B. J. Chem. Educ. 1970, 47, A122.
Synthesis
Stereochemical correlations in the norbornane system  Markgraf, J. Hodge; Leung, Pak-Tong
In this experiment 2-norbornanone is converted to the epimeric 2-methyl-2-norbornanols by two routes; the structural assignments of the products are not specified, but must be determined from comparisons of various physical properties.
Markgraf, J. Hodge; Leung, Pak-Tong J. Chem. Educ. 1970, 47, 707.
Stereochemistry |
Molecular Properties / Structure |
Synthesis
Aromatic nitro musk synthesis  Nash, E. Gary; Nienhouse, Everett J.; Silhavy, Thomas A.; Humbert, Dale E.; Mish, Mary Jo
This synthesis involves the preparation of the nitro-musks, musk xylene and/or musk ketone, from readily available m-xylene.
Nash, E. Gary; Nienhouse, Everett J.; Silhavy, Thomas A.; Humbert, Dale E.; Mish, Mary Jo J. Chem. Educ. 1970, 47, 705.
Aromatic Compounds |
Synthesis
Convenient procedure for the preparation of potassium trioxalatoferrate(III)  Johnson, Ronald C.
This note provides a convenient procedure for the preparation of potassium trioxalatoferrate(III), which can be quantitatively analyzed for water, iron, and oxalate by standard procedures frequently taught in beginning courses.
Johnson, Ronald C. J. Chem. Educ. 1970, 47, 702.
Synthesis
Project orientation in the organic laboratory  Neckers, Douglas C.
Reported herein is an independent synthesis sequence involving the synthesis of dicyclopropyl ketone; once produced, students are asked to "do something with the product."
Neckers, Douglas C. J. Chem. Educ. 1970, 47, 700.
Synthesis
Preparation of the proteins by micro-organisms  Dieteren, H. M. L.; Schouteten, A. P. H.
Yeast are used to generate proteins from tetradecane in a controlled vessel.
Dieteren, H. M. L.; Schouteten, A. P. H. J. Chem. Educ. 1970, 47, 663.
Proteins / Peptides |
Synthesis
Preparation of 6-aminosaccharin  Rose, Norman C.; Rome, Sanford
This synthesis involves the substitution of a chlorosulfonyl group onto an aromatic ring at a position predictable on the basis of the directing ability of the groups already present, the oxidation of a methyl group, a cyclization that is an example of the ease with which five-membered rings are formed, and the reduction of a nitro group.
Rose, Norman C.; Rome, Sanford J. Chem. Educ. 1970, 47, 649.
Synthesis |
Aromatic Compounds |
Oxidation / Reduction
The photoaddition of maleic anhydride to benzene: A simple organic experiment in a complicated system  Bozak, R. E.; Alvarez, V. E.
Presents the photochemical synthesis of benzopinacol as a pedagogical example of organic photochemistry suitable for the first-year organic course.
Bozak, R. E.; Alvarez, V. E. J. Chem. Educ. 1970, 47, 589.
Photochemistry |
Aromatic Compounds |
Synthesis
Acid hydrolysis of nylon 66  Berkowitz, W. F.
Presents a procedure for the hydrolysis of nylon 66.
Berkowitz, W. F. J. Chem. Educ. 1970, 47, 536.
Polymerization |
Synthesis
Synthesis and NMR spectrum of triphenyltin hydride: An organometallic chemistry experiment  Allen, Christopher W.
This experiment reacts an alkali metal salt of the triphenylstannyl ion with the ammonium ion in liquid ammonia and employs NMR to identify different isotopes of tin in the resulting product.
Allen, Christopher W. J. Chem. Educ. 1970, 47, 479.
Synthesis |
Organometallics |
NMR Spectroscopy |
Isotopes
Synthesis of cyclopentanecarboxaldehyde: An undergraduate organic chemistry laboratory experiment  Dev, Vasu
The synthesis of cyclopentanecarboxaldehyde can be applied to develop an understanding of the behavior of compounds in many areas of organic chemistry, particularly those of alicyclic compounds.
Dev, Vasu J. Chem. Educ. 1970, 47, 476.
Synthesis |
Aldehydes / Ketones |
Mechanisms of Reactions |
Nucleophilic Substitution
Inorganic synthesis in undergraduate research  Gorman, Mel; DeMattia, Dennis; Doonan, Daniel; McDonald, Gary
Describes a project in which an undergraduate team succeeded in synthesizing a compound never before produced.
Gorman, Mel; DeMattia, Dennis; Doonan, Daniel; McDonald, Gary J. Chem. Educ. 1970, 47, 466.
Synthesis |
Undergraduate Research
Grignard: "Concerning organomagnesium compounds in solution and their application to the synthesis of acids, alcohols, and hydrocarbons"  Jones, Paul R.; Southwick, Everett (translators)
A translation of Grinard's paper announcing the formation of alkylmagnesium compounds in ether, based on his doctoral dissertation.
Jones, Paul R.; Southwick, Everett (translators) J. Chem. Educ. 1970, 47, 290.
Organometallics |
Grignard Reagents |
Synthesis
The preparation of aminoboranes: Two high vacuum experiments for inorganic chemistry laboratory  Spielman, John R.
Procedures for the synthesis of N,N-dimethylaminoborane and mu-dimethylaminoborane.
Spielman, John R. J. Chem. Educ. 1970, 47, 225.
Synthesis
The synthesis of 2-nitroresorcinol: An experiment with sulfonic acids  Schaffrath, Robert E.
This synthesis is an ideal example using the -SO3H as a blocking group.
Schaffrath, Robert E. J. Chem. Educ. 1970, 47, 224.
Synthesis |
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure
Preparation of 2-arylimidazo-(2,1-b)benzothiazoles: An experiment in organic chemistry  Alper, Howard
This paper describes the synthesis of a fused ring system by a simple cyclization reaction.
Alper, Howard J. Chem. Educ. 1970, 47, 223.
Heterocycles |
Synthesis
Isopoly and heteropoly compounds: A general chemistry laboratory experiment  Kauffman, George B.; Vartanian, Paul F.
This procedure involves the preparation of isopoly and heteropoly salts and introduces the beginning student to liquid-liquid extraction, titration, ion exchange, conductance, and a variety of synthetic and analytical techniques.
Kauffman, George B.; Vartanian, Paul F. J. Chem. Educ. 1970, 47, 212.
Synthesis |
Acids / Bases |
Electrochemistry
Preparation of the members of an homologous series: An organic chemistry experiment  Kolenbrander, Harold M.
This article describes an experiment involving the synthesis of S-alkyl derivatives of homocysteine.
Kolenbrander, Harold M. J. Chem. Educ. 1970, 47, 56.
Synthesis |
Molecular Properties / Structure |
Alkylation
Biosynthesis of an antibiotic: A 14C tracer experiment  Glover, I. T.; Limbaugh, C. L.
This experiment involves the incorporation of 14C into the antibiotic citrinin and a two-step degradation series that allows students to decide between two alternate routes of biosynthesis.
Glover, I. T.; Limbaugh, C. L. J. Chem. Educ. 1969, 46, 866.
Synthesis |
Isotopes |
Drugs / Pharmaceuticals |
Medicinal Chemistry
Economics in the chemical industry. Part II  Reese, K. M.
Focusses on the production of ethylene, aspirin, nylon, DDT, and fluorocarbon-12 since WWII.
Reese, K. M. J. Chem. Educ. 1969, 46, 827.
Industrial Chemistry |
Alkenes |
Synthesis
Recent developments in the use or organoboranes in organic synthesis  Cragg, G. M. L.
A review of organic synthesis reactions involving organoboranes.
Cragg, G. M. L. J. Chem. Educ. 1969, 46, 794.
Synthesis |
Reactions
Historical origins of organometallic chemistry. Part II, Edward Frankland and diethylzinc  Thayer, John S.
Considers Edward Frankland and his preparation of diethylzinc.
Thayer, John S. J. Chem. Educ. 1969, 46, 764.
Organometallics |
Synthesis
Oxidative coupling: A new approach to azo chemistry  Hunig, S.
By looking for the important structural features of p-phenylenediamines that constitute their ability to couple oxidatively, it was possible to construct three new systems that are also capable of undergoing this reaction. The enormous variety possible in these systems permits the syntheses of a great number of unusual azo compounds.
Hunig, S. J. Chem. Educ. 1969, 46, 734.
Aromatic Compounds |
Oxidation / Reduction |
Mechanisms of Reactions |
Synthesis
A very stable monomeric nitrosyldisulfonate salt  Goodgame, D. M. L.
A brief note on the preparation of (o-xylene-bistriphenylphosphonium)Br2 [abbreviated (o-cat)Br2].
Goodgame, D. M. L. J. Chem. Educ. 1969, 46, 724.
Synthesis
Preparation of sulfanilamide from aniline: An organic chemistry experiment  Hurdis, Everett C.; Yang, Josephine W.
Presents the preparation of sulfanilamide from aniline, a synthesis that is shorter than the tradition method.
Hurdis, Everett C.; Yang, Josephine W. J. Chem. Educ. 1969, 46, 697.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
The Hantzsch pyridine synthesis: A factorial design experiment for the introductory organic laboratory  Norcross, B. E.; Clement, G.; Weinstein, M.
Students carry out the two-step Hantzsch pyridine synthesis; students are required to select the oxidizing agent and conditions for the second reaction step.
Norcross, B. E.; Clement, G.; Weinstein, M. J. Chem. Educ. 1969, 46, 694.
Synthesis |
Oxidation / Reduction |
Heterocycles |
Mechanisms of Reactions
Preparation of adamantane: An introductory organic experiment  Ault, Addison; Kopet, Rachel
This preparation involves the aluminum chloride catalyzed isomerization of endo-tetrahydrodicyclopentadiene.
Ault, Addison; Kopet, Rachel J. Chem. Educ. 1969, 46, 612.
Synthesis |
Catalysis
The historical and current interest in coumarin  Abernethy, John Leo
Examines the historic isolation of coumarin, its uses, and an industrial synthesis.
Abernethy, John Leo J. Chem. Educ. 1969, 46, 561.
Applications of Chemistry |
Synthesis
Electrolytic preparation of iodoform  Helle, K.; Rijks, J. A.; Janssen, L. J. J.; Schuyl, J. W.
This short note describes a simplified method for the production of iodoform.
Helle, K.; Rijks, J. A.; Janssen, L. J. J.; Schuyl, J. W. J. Chem. Educ. 1969, 46, 518.
Electrochemistry |
Synthesis |
Laboratory Equipment / Apparatus |
Laboratory Management
Synthesis and reactions of cobalt complexes: A laboratory experiment  Olson, Gary L.
The experiment described here studies a series of reactions employed in the synthesis of a number of coordination compounds of cobalt(II) and cobalt(III).
Olson, Gary L. J. Chem. Educ. 1969, 46, 508.
Coordination Compounds |
Synthesis
A research approach in the introductory laboratory  Wilson, Lauren R.
Presents an alternative to artificial "experiments" in which known results are merely confirmed in which students synthesize a series of chloro-ammine and chloro-ethylene-diaminecobalt(III) compounds.
Wilson, Lauren R. J. Chem. Educ. 1969, 46, 447.
Undergraduate Research |
Synthesis |
Coordination Compounds |
Qualitative Analysis
Historical origins of organometallic chemistry. Part I, Zeise's salt  Thayer, John S.
Traces the synthesis and analysis of potassium trichloro(theylene)platinate(II) monohydrate, named Zeise's salt in honor of its discoverer.
Thayer, John S. J. Chem. Educ. 1969, 46, 442.
Organometallics |
Metals |
Coordination Compounds |
Synthesis |
Transition Elements
Alicyclic chemistry: The playground for organic chemists  Ferguson, Lloyd N.
This article reviews a number of general topics that have been of special interest in alicyclic chemistry, including conformational analysis, the nonclassical versus classical norbornyl cation, Woodward-Hoffmann electrolytic rules, the aromaticity of nonbenzoid rings, strained ring systems, bridgehead activity, and photochemical syntheses and rearrangements.
Ferguson, Lloyd N. J. Chem. Educ. 1969, 46, 404.
Conformational Analysis |
Synthesis |
Photochemistry
Reactions on basic alumina  Serratosa, Felix
Provides a survey of the use of alumina in synthetic and mechanistic studies.
Serratosa, Felix J. Chem. Educ. 1969, 46, 302.
Synthesis |
Mechanisms of Reactions
Kinetics of condensation polymerization: Preparation of a polyester  McCaffery, Edward L.
This experiment involves determining the reaction-rate constant for a condensation polymerization.
McCaffery, Edward L. J. Chem. Educ. 1969, 46, 59.
Kinetics |
Polymerization |
Synthesis |
Esters |
Rate Law
A novel synthesis of magnesium carbide  Lauren, Paul M.
Demonstrates the synthesis of magnesium carbide from calcium carbide and magnesium ribbon.
Lauren, Paul M. J. Chem. Educ. 1968, 45, A569.
Synthesis
Inorganic syntheses, volume 10 (Muetterties, Earl L.)  Kauffman, George B.

Kauffman, George B. J. Chem. Educ. 1968, 45, A436.
Synthesis
Synthetic methods of organic chemistry (Theilheimer, W.)  Becker, Ernest I.

Becker, Ernest I. J. Chem. Educ. 1968, 45, A336.
Synthesis
Carbon and its inorganic compounds. C. Carbon dioxide   Colo, August J.; Alyea, Hubert N.
Demonstrates the production of CO2 from dry ice and limestone and acid.
Colo, August J.; Alyea, Hubert N. J. Chem. Educ. 1968, 45, A326.
Gases |
Synthesis
Carbon and its inorganic compounds. B. Carbon monoxide   Colo, August J.
Demonstrates the formation of carbon monoxide.
Colo, August J. J. Chem. Educ. 1968, 45, A326.
Gases |
Synthesis
The formaldehyde centenary  Farber, Eduard
Examines the first production of and early investigations involving formaldehyde.
Farber, Eduard J. Chem. Educ. 1968, 45, 812.
Aldehydes / Ketones |
Synthesis
Preparation of nickel sulfides (the authors reply)  Dingledy, David; Barnard, Walther M.
An alternative method for the preparation of nickel sulfides.
Dingledy, David; Barnard, Walther M. J. Chem. Educ. 1968, 45, 750.
Synthesis
Preparation of nickel sulfides  Callen, John B.; Crouch, Stanley R.; Haight, Gilbert P., Jr.
An alternative method for the preparation of nickel sulfides.
Callen, John B.; Crouch, Stanley R.; Haight, Gilbert P., Jr. J. Chem. Educ. 1968, 45, 750.
Synthesis
The Hofmann amide rearrangement  Schreck, James O.
N-bromobenzamide and phenyl isocyanate are subjected to the same conditions required to convert benzamide to aniline to demonstrate that the former two compounds could be intermediates in the Hofmann rearrangements of benzamide.
Schreck, James O. J. Chem. Educ. 1968, 45, 670.
Amides |
Synthesis |
Mechanisms of Reactions
Acids as derivatives of aldehydes prepared with silver oxides  Thomason, Sandra C.; Kubler, Donald G.
Examines the use of silver(i) and silver(II) oxide to convert aldehydes into acid derivatives.
Thomason, Sandra C.; Kubler, Donald G. J. Chem. Educ. 1968, 45, 546.
Acids / Bases |
Aldehydes / Ketones |
Oxidation / Reduction |
Synthesis
Reagents for organic synthesis (Fieser, L. F.; Fieser, M.)  Puterbaugh, M. P.

Puterbaugh, M. P. J. Chem. Educ. 1968, 45, 496.
Synthesis
A simple preparation of sulfanilic acid  Roeges, Noel
A short note concerning the preparation of sulfanilic acid.
Roeges, Noel J. Chem. Educ. 1968, 45, 274.
Acids / Bases |
Synthesis
The generation of benzyne - A warning  Mich, Thomas F.; Nienhouse, Everett J.; Farino, Thomas E.; Tufariello, Joseph J.
The synthesis of benzyne by the diazotization of anthranilic acid may result in an explosion; an improved procedure to avoid this problem is presented.
Mich, Thomas F.; Nienhouse, Everett J.; Farino, Thomas E.; Tufariello, Joseph J. J. Chem. Educ. 1968, 45, 272.
Aromatic Compounds |
Synthesis
Pseudohalogens: A general chemistry laboratory experiment  Kauffman, George B.; Foust, Gary E.; Tun, Peggy
This experiment focusses on the synthesis, properties, and reactions of cyanogen and thiocyanogen.
Kauffman, George B.; Foust, Gary E.; Tun, Peggy J. Chem. Educ. 1968, 45, 141.
Synthesis
Preparation and characterization of mesitylene tricarbonyl molybdenum (O): An experiment in organometallic chemistry  Angelici, Robert J.
This procedure illustrates a preparation conducted under an inert atmosphere, compound purification by sublimation, and identification of a product by infrared and proton nuclear magnetic resonance and mass spectroscopy.
Angelici, Robert J. J. Chem. Educ. 1968, 45, 119.
Organometallics |
Synthesis |
Spectroscopy |
IR Spectroscopy |
Mass Spectrometry
The Eschweiler-Clark methylation of amines: An organic chemistry experiment  Pine, Stanley H.
In this procedure, benzylamine is converted to N,N-dimethylbenzylamine.
Pine, Stanley H. J. Chem. Educ. 1968, 45, 118.
Amines / Ammonium Compounds |
Synthesis
Letter to the editor  Winterburn, John
Praises the usefulness of an earlier published synthesis.
Winterburn, John J. Chem. Educ. 1968, 45, 70.
Synthesis |
Aromatic Compounds
3-Sulfolene: A butadiene source for a Diels-Alder synthesis: An undergraduate laboratory experiment  Sample, Thomas E., Jr.; Hatch, Lewis F.
By selecting a suitable diene cyclic sulfone, the common complication in performing a Diels-Alder experiment can be avoided.
Sample, Thomas E., Jr.; Hatch, Lewis F. J. Chem. Educ. 1968, 45, 55.
Alkenes |
Synthesis |
Mechanisms of Reactions
Inorganic syntheses, Volume 8 (Holtzclaw, Henry F., Jr.)  Kauffman, George B.

Kauffman, George B. J. Chem. Educ. 1967, 44, A354.
Synthesis
A multipurpose coordination chemistry experiment for undergraduates  Burmeister, John L.
This experiment involves the three-step synthesis of K3[Co(CN)5SCN].
Burmeister, John L. J. Chem. Educ. 1967, 44, 769.
Coordination Compounds |
Synthesis
The stoichiometry of sulfides: Experiments for the introductory laboratory  Dingledy, David
Uses the preparation of lead sulfide and nickel sulfide to illustrate the law of constant proportions.
Dingledy, David J. Chem. Educ. 1967, 44, 693.
Stoichiometry |
Synthesis
Inorganic syntheses. Volume 9 (Tyree, S. Young, Jr.)  Kauffman, George B.

Kauffman, George B. J. Chem. Educ. 1967, 44, 624.
Synthesis
Letter to the editor  Bacon, E. K.
Examines values collected when using the production of copper sulfide to demonstrate the law of constant proportions.
Bacon, E. K. J. Chem. Educ. 1967, 44, 620.
Stoichiometry |
Synthesis
The preparation of naphthalene-alpha-d: An experiment in organic chemistry  Ziegler, Gene R.
This procedure involves the preparation of a hydrocarbon via the Grignard reagent from the corresponding bromide.
Ziegler, Gene R. J. Chem. Educ. 1967, 44, 609.
Synthesis |
Grignard Reagents |
Alkanes / Cycloalkanes
Acid anhydride functionality  Hurd, Charles D.
Examines several different structural types, each of which posses the acid anhydride functionality, though most are named on a different basis.
Hurd, Charles D. J. Chem. Educ. 1967, 44, 454.
Acids / Bases |
Synthesis |
Mechanisms of Reactions
Determination of the combining weight of tin: A new look at an old experiment  Carmody, Walter R.
Describes efforts to improve the determination of the combining weight of tin
Carmody, Walter R. J. Chem. Educ. 1967, 44, 416.
Stoichiometry |
Oxidation / Reduction |
Reactions |
Synthesis
Syntheses and titrations of unknown acids: A general chemistry laboratory experiment  Kauffman, George B.; Houghten, Richard A., Jr.
Students prepare a solid unknown acid from an unknown starting material and then determine its equivalent weight by titration with a standard base.
Kauffman, George B.; Houghten, Richard A., Jr. J. Chem. Educ. 1967, 44, 408.
Acids / Bases |
Synthesis |
Titration / Volumetric Analysis
Preparation of terephthaloyl chloride: Prelude to ersatz Nylon  Rose, Norman C.
Describes the preparation of terephthaloyl chloride, from which nylon may be generated.
Rose, Norman C. J. Chem. Educ. 1967, 44, 283.
Synthesis |
Polymerization
Alcohols to alkyl halides: A kinetics experiment for elementary chemistry courses  Cooley, J. H.; McCown, J. D.; Shill, R. M.
The rate measurement in this procedure is accomplished by direct observation of the change in length or volume of the insoluble layer of an alkyl bromide that is formed from a mixture of alcohol, hydrobromic acid, and sulfuric acid.
Cooley, J. H.; McCown, J. D.; Shill, R. M. J. Chem. Educ. 1967, 44, 280.
Alcohols |
Synthesis |
Kinetics |
Rate Law
The stoichiometry of copper sulfide formed in an introductory laboratory exercise  Dingledy, David; Barnard, Walther M.
The preparation of copper sulfide is used as an introductory chemistry laboratory exercise to demonstrate the law of constant proportions.
Dingledy, David; Barnard, Walther M. J. Chem. Educ. 1967, 44, 242.
Stoichiometry |
Synthesis
Student experiments involving unknown solubility constants  Heinz, D. E.
Insoluble metallic salts of sorbic and cinnamic acid are synthesized and characterized, and their solubilities in various solvents under many conditions are investigated.
Heinz, D. E. J. Chem. Educ. 1967, 44, 114.
Precipitation / Solubility |
Synthesis
Equipment for use in organic synthesis  Hoehn, W. M.; Johnston, J. Derland
Stainless steel milk cans and soft drink dispensers have been adapted for certain operations in organic chemical synthesis to replace five-gallon Pyrex glass bottles.
Hoehn, W. M.; Johnston, J. Derland J. Chem. Educ. 1966, 43, 537.
Laboratory Equipment / Apparatus |
Synthesis
1-bromo-3-chloro-5-iodobenzene: An eight-step synthesis from benzene  Ault, Addison; Kraig, Raymond
Presents an eight-step synthesis of 1-bromo-3-chloro-5-iodobenzene from benzene.
Ault, Addison; Kraig, Raymond J. Chem. Educ. 1966, 43, 213.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions
Preparation of ethylaluminum sesqui-iodide: A lecture demonstration  Krahe, Eduard; Rochow, E. G.
The preparation of ethylaluminum sesqui-iodide has been selected as the best method for demonstrating a direct synthesis of an organometallic compound.
Krahe, Eduard; Rochow, E. G. J. Chem. Educ. 1966, 43, 63.
Organometallics |
Synthesis
The direct synthesis of organometallic compounds  Rochow, Eugene G.
Examines the direct synthesis of organometallic compounds.
Rochow, Eugene G. J. Chem. Educ. 1966, 43, 58.
Synthesis |
Organometallics |
Metals
Modern synthetic reactions (House, H. O.)  Meinwald, Jerrold

Meinwald, Jerrold J. Chem. Educ. 1965, 42, A910.
Synthesis |
Reactions
Organometallic syntheses. Volume 1, Transition-metal compounds (King, R. B.)  Cowan, Dwaine O.

Cowan, Dwaine O. J. Chem. Educ. 1965, 42, 691.
Organometallics |
Synthesis |
Transition Elements |
Metals
The synthesis of carbocyclic compound: A historical survey  Finley, K. Thomas
Reviews the development of ring closure reactions.
Finley, K. Thomas J. Chem. Educ. 1965, 42, 536.
Synthesis |
Alkanes / Cycloalkanes
More on Berzelius and the vital force (the author replies)  Lipman, Timothy O.
Comments on the cited letter.
Lipman, Timothy O. J. Chem. Educ. 1965, 42, 396.
Synthesis
More on Berzelius and the vital force  Jorgensen, Bent Soren
The significance of Wohler's synthesis is heavily overestimated in most textbooks and gives the student a totally false impression of historical reality.
Jorgensen, Bent Soren J. Chem. Educ. 1965, 42, 394.
Synthesis
Demonstration of transketolase activity in plant leaves: Synthesis of L-glucoheptulose  Abernethy, John Leo
This experiment utilizes only simple chromatographic apparatus to illustrate a basic biochemical reaction.
Abernethy, John Leo J. Chem. Educ. 1965, 42, 286.
Plant Chemistry |
Synthesis |
Chromatography
A modification and extension of an elementary preparation of ninhydrin  Gruen, H.; Norcross, B. E.
The modification presented for the multistep synthesis of ninhydrin avoids the need for finely divided metallic sodium by using a semisolid 50% suspension of sodium hydride in mineral oil.
Gruen, H.; Norcross, B. E. J. Chem. Educ. 1965, 42, 268.
Synthesis
A three-step synthesis: 2,4-Dinitrophenylhydrazine from benzene  Ault, Addison
Presents a synthetic sequence for use in the introductory organic chemistry laboratory: the synthesis of 2,4-dinitrophenylhydrazine from benzene by way of bromobenzene and 2,4-dinitrobromobenzene.
Ault, Addison J. Chem. Educ. 1965, 42, 267.
Synthesis |
Aromatic Compounds |
Mechanisms of Reactions |
Reactions
The biosynthesis of fatty acids  Gibson, David M.
Examines the biosynthesis of fatty acids, including fatty acid oxidation, the synthesis of saturated fatty acids, and the control of fatty acid synthesis
Gibson, David M. J. Chem. Educ. 1965, 42, 236.
Synthesis |
Lipids |
Fatty Acids
Thermally stable polymeric materials  Bruck, S. D.
The object of this article is to discuss some of the factors responsible for high thermal stability in polymers, to review a few of the most important advances that have recently been made in the synthesis of such materials, and to present some of the results of the thermal degradation of an aromatic polyimide under investigation in the author's laboratory.
Bruck, S. D. J. Chem. Educ. 1965, 42, 18.
Synthesis |
Aromatic Compounds |
Thermal Analysis
Polymer synthesis in the undergraduate organic laboratory  Sorenson, Wayne R.
Presents a series of experiments on polymer synthesis for the undergraduate organic laboratory.
Sorenson, Wayne R. J. Chem. Educ. 1965, 42, 8.
Synthesis |
Polymerization |
Reactions |
Mechanisms of Reactions
Compound semiconductors. Volume 1, Preparation of III-V compounds (Willardson, Robert K.; Goering, Harvey L.; ed.s)  Foster, Laurence S.

Foster, Laurence S. J. Chem. Educ. 1964, 41, A472.
Semiconductors |
Solid State Chemistry |
Synthesis
Free Radical Reactions in Preparative Organic Chemistry (Sosnovsky, George)  Stacey, F. W.

Stacey, F. W. J. Chem. Educ. 1964, 41, 691.
Free Radicals |
Reactions |
Synthesis
Constitutional Problems in Organic Chemistry (Watson, M. B.; Youngson, G. W.)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1964, 41, 691.
Reactions |
Synthesis
Infrared spectrometry to study second order reaction kinetics  Gastambide, B.; Blanc, J.; Allamagny, Y.
The change studied is a synthesis reaction between menthol and phenyl isocyanate.
Gastambide, B.; Blanc, J.; Allamagny, Y. J. Chem. Educ. 1964, 41, 613.
Spectroscopy |
IR Spectroscopy |
Reactions |
Kinetics |
Synthesis
Aqueous bromination with bromine chloride: A simplified method for the preparation of 2,6-dibromo-4-nitrophenol  Obenland, C. O.
The classic preparation of 2,6-dibromo-4-nitrophenol can be shortened and simplified by using bromine chloride in aqueous solution.
Obenland, C. O. J. Chem. Educ. 1964, 41, 566.
Synthesis |
Phenols |
Aqueous Solution Chemistry
The amine catalyzed Perkin condensation: A class project  Ketcham, Roger
In this exercise students carry out the amine catalyzed Perkin condensations of substituted benzaldehydes with substituted phenylacetic acids to give alpha-phenyl-cis- and trans-cinnamic acids.
Ketcham, Roger J. Chem. Educ. 1964, 41, 565.
Amines / Ammonium Compounds |
Catalysis |
Reactions |
Synthesis
Basic alumina: Source of dihalocarbenes. For organic laboratory experiments  Serratosa, Felix
Describes the preparation of dihalocarbenes using a chromatographic column and basic alumina.
Serratosa, Felix J. Chem. Educ. 1964, 41, 564.
Synthesis
The discovery of a new class of compounds: Carboranes  Bobinski, Jack
The first member of a new class of carborane compounds, 1-isopropenylcarborane, was discovered during a broad-scale investigation of the use of boron hydrides as propellants for the U.S. Air Force.
Bobinski, Jack J. Chem. Educ. 1964, 41, 500.
Synthesis
Synthetic methods of organic chemistry. Volume 16 (Theilheimer, W.)  Becker, Ernest I.

Becker, Ernest I. J. Chem. Educ. 1964, 41, 464.
Synthesis
Wohler's preparation of urea and the fate of vitalism  Lipman, Timothy O.
Organic chemistry as we know it was not immediately established with Wohler's preparation of urea, nor was it solely responsible for overthrowing vitalistic doctrine.
Lipman, Timothy O. J. Chem. Educ. 1964, 41, 452.
Synthesis
Letters  Ferry, N.
Describes a shorter method for preparing 2,4-dinitroaniline.
Ferry, N. J. Chem. Educ. 1964, 41, 404.
Synthesis
An improved method for preparing S-alkylisothiouronium picrates  Crosby, Howard M.; Entrikin, John B.
Presents an improved method for preparing S-alkylisothiouronium picrate derivatives of primary and secondary alkyl halides.
Crosby, Howard M.; Entrikin, John B. J. Chem. Educ. 1964, 41, 360.
Synthesis
Newer methods of preparative organic chemistry. Volume 2 (Foerst, Wilhelm, ed.)  Zook, Harry D.

Zook, Harry D. J. Chem. Educ. 1964, 41, 350.
Synthesis
Boron-nitrogen heterocycles  Payne, Dwight A., Jr.; Eads, Ewin A.
Examines the synthesis, reactions, and toxicity of boron-nitrogen heterocycles.
Payne, Dwight A., Jr.; Eads, Ewin A. J. Chem. Educ. 1964, 41, 334.
Heterocycles |
Synthesis |
Reactions |
Toxicology
Ficin as a catalyst in organic syntheses  Abernethy, John Leo; Leonardo, Gilbert L.
Examines the chemistry of ficin, particularly its catalytic behavior, and suggests experiments involving this natural substance.
Abernethy, John Leo; Leonardo, Gilbert L. J. Chem. Educ. 1964, 41, 53.
Catalysis |
Synthesis
Inorganic synthesis. Volume 7 (Kleinberg, Jacob, ed.)  Kauffman, George B.

Kauffman, George B. J. Chem. Educ. 1963, 40, A530.
Synthesis
PolystyreneA multistep synthesis  Wilen, S. H.
Suggestions for research to accompany a previously published article.
Wilen, S. H. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Polymerization |
Synthesis
Apparatus for the Friedel-Crafts reaction  Kremer, C. B.
Suggestions for research to accompany a previously published article.
Kremer, C. B. J. Chem. Educ. 1963, 40, A463.
Undergraduate Research |
Reactions |
Synthesis
Luminescent compounds, i.e., phosphors  Tietze, H. R.
Describes the production of strontium sulfide and cadmium chlorophosphate phosphor. [Author's name was misspelled, corrected on p. A241, March 1963 (but the correction misidentifies the issue in which the error occurred as Dec 1962 rather than Jan 1963).]
Tietze, H. R. J. Chem. Educ. 1963, 40, A49.
Synthesis
Simple method for the preparation of 2,4-dinitroaniline  Ashton, A. A.
The author found that 2,4-dinitroaniline could be conveniently prepared by refluxing 2,4-dinitrochlorobenzene in an alcoholic solution with concentrated ammonia.
Ashton, A. A. J. Chem. Educ. 1963, 40, 545.
Synthesis
An improved synthesis of 2-bromonaphthalene  Vingiello, F. A.; Delia, T. J.; Polss, P.; Farrier, D.
Describes an improved synthesis for the large-scale preparation of 2-bromonaphthalene.
Vingiello, F. A.; Delia, T. J.; Polss, P.; Farrier, D. J. Chem. Educ. 1963, 40, 544.
Synthesis
A Diels-Alder student preparation  Kellett, J. C., Jr.
A Diels-Alder reaction between tetracyanoethylene and anthracene serves as a rapid student preparation for a course in organic chemistry for pharamacy students.
Kellett, J. C., Jr. J. Chem. Educ. 1963, 40, 543.
Synthesis
Preparation and analysis of a complex compound  Sebera, Donald K.
A cobalt/ammonia complex is prepared and analyzed in a freshman chemistry laboratory.
Sebera, Donald K. J. Chem. Educ. 1963, 40, 476.
Synthesis |
Coordination Compounds |
Transition Elements
Organis syntheses. Volume 42, 1962 (Boekelheide, Virgil, ed.)  Haynes, LeRoy W.

Haynes, LeRoy W. J. Chem. Educ. 1963, 40, 443.
Synthesis
High pressure techniques for microscale reactions  Rhodes, Richard P.
presents examples of pressure vessels that have been designed and tested for microscale organic syntheses studies.
Rhodes, Richard P. J. Chem. Educ. 1963, 40, 423.
Microscale Lab |
Reactions |
Synthesis
Esterification for the introductory organic laboratory course: A modified Dean-Stark trap  Puterbaugh, W. H.; Vanselow, C. H.; Nelson, K.; Shrawder, E. J.
Describes a simplified construction for a Dean-Stark trap and its use to determine optimum conditions for the preparation of n-amul acetate.
Puterbaugh, W. H.; Vanselow, C. H.; Nelson, K.; Shrawder, E. J. J. Chem. Educ. 1963, 40, 349.
Esters |
Synthesis
alpha-Pinene, a starting material for a sequence of organic experiments  Dominguez, X. A.; Leal, G.
This paper presents a unified sequence of experiments that illustrates the unit operations and unit processes of organic chemistry and includes rearrangements and stereoisomerism exemplified by the chemistry of the terpenes.
Dominguez, X. A.; Leal, G. J. Chem. Educ. 1963, 40, 347.
Synthesis |
Reactions |
Mechanisms of Reactions |
Stereochemistry |
Molecular Properties / Structure
Preparation of diphenylmethane. Simplified procedure: purer product  Ellis, William D.
These modified procedures for the preparation of diphenylmethane are intended the eliminate the formation of impurities.
Ellis, William D. J. Chem. Educ. 1963, 40, 346.
Synthesis
Uses of electrical discharges in preparative inorganic chemistry  Massey, Alan G.
Examines the preparation of some unusual compounds using glow discharge at low pressure, silent electric discharge, and microwave discharge.
Massey, Alan G. J. Chem. Educ. 1963, 40, 311.
Synthesis |
Electrochemistry
Friedel-Crafts alkylation  Marsi, Kenneth L.; Wilen, Samuel H.
Some organic textbooks state that n-alkyl derivatives cannot be synthesized by the Friedel-Crafts reaction, or that they are formed in only minor amounts, though this is not the case.
Marsi, Kenneth L.; Wilen, Samuel H. J. Chem. Educ. 1963, 40, 214.
Reactions |
Synthesis
The decarboxylation of organic acid  March, Jerry
Simple aliphatic acids (except for acetic) do not give good yields of the corresponding alkanes through decarboxylation, although many organic chemistry textbooks cite this as a general method for the preparation of alkanes.
March, Jerry J. Chem. Educ. 1963, 40, 212.
Acids / Bases |
Reactions |
Synthesis |
Alkanes / Cycloalkanes |
Carboxylic Acids
The chemistry of enamines  West, Joseph A.
Presents the properties, preparation, and important applications of enamines.
West, Joseph A. J. Chem. Educ. 1963, 40, 194.
Synthesis |
Reactive Intermediates |
Reactions |
Mechanisms of Reactions |
Amines / Ammonium Compounds
Project syntheses for organic laboratory courses  Bunce, Stanley C.
Presents a listing of compounds suitable for assignment in the elementary organic laboratory course and rates the synthetic difficulty of each.
Bunce, Stanley C. J. Chem. Educ. 1963, 40, 174.
Synthesis
Student preparation and manipulation of a gasMethyl ethyl ether  Casanova, Joseph, Jr.
This laboratory involves the preparation of methyl ethyl ether by a Williamson synthesis.
Casanova, Joseph, Jr. J. Chem. Educ. 1963, 40, 41.
Ethers |
Synthesis |
Gases
Synthetic methods of organic chemistry, volume 15 (Theilheimer, W.)  Becker, Ernest I.

Becker, Ernest I. J. Chem. Educ. 1962, 39, A982.
Synthesis
Laboratory experiments dealing with the manufacture of paints  Young, Jay A.; Taylor, John K.
Suggests some research activities based on an article published previously in the Journal.
Young, Jay A.; Taylor, John K. J. Chem. Educ. 1962, 39, A962.
Industrial Chemistry |
Synthesis |
Dyes / Pigments |
Undergraduate Research
The preparation of nitrosobenzene  Young, Jay A.; Taylor, John K.
Suggests some research activities based on an article published previously in the Journal.
Young, Jay A.; Taylor, John K. J. Chem. Educ. 1962, 39, A962.
Synthesis |
Aromatic Compounds |
Undergraduate Research
The preparation of magnesium nitride  Young, Jay A.; Taylor, John K.
Suggests some research activities based on an article published previously in the Journal.
Young, Jay A.; Taylor, John K. J. Chem. Educ. 1962, 39, A960.
Synthesis |
Undergraduate Research |
Reactions
Organic Syntheses. Volume 41 (Roberts, John D., ed.)  Reinheimer, John D.

Reinheimer, John D. J. Chem. Educ. 1962, 39, A832.
Synthesis
The chemical formulary. Volume 11 (Bennett, H., ed.)  Kieffer, William F.

Kieffer, William F. J. Chem. Educ. 1962, 39, A332.
Synthesis
Use of magnesium sulfate in the preparation of anhydrous ether  Burgstahler, A. W.; Kulier, C. P.; Worden, L. R.
This short note describes the use of magnesium sulfate in the preparation of anhydrous ether.
Burgstahler, A. W.; Kulier, C. P.; Worden, L. R. J. Chem. Educ. 1962, 39, 578.
Ethers |
Synthesis |
Laboratory Management
Preparation of hydrazoic acid by ion exchange techniques  Bryant, J. I.; Rosenwasser, H.
Describes the preparation of hydrazoic acid by ion exchange.
Bryant, J. I.; Rosenwasser, H. J. Chem. Educ. 1962, 39, 296.
Synthesis |
Acids / Bases |
Ion Exchange
A student preparation of butyl ether  Smith, William B.
This preparation uses a Dean-Stark tube to separate water from the reaction mixture as it is formed.
Smith, William B. J. Chem. Educ. 1962, 39, 212.
Ethers |
Synthesis |
Laboratory Equipment / Apparatus
The acylation of aliphatic unsaturated hydrocarbons  Sharefkin, Jacob G.
Introductory organic chemistry textbooks discuss the Friedel-Crafts synthesis of aromatic ketones but usually do not treat the corresponding reaction in the aliphatic series.
Sharefkin, Jacob G. J. Chem. Educ. 1962, 39, 206.
Aromatic Compounds |
Aldehydes / Ketones |
Reactions |
Synthesis |
Mechanisms of Reactions
The nature of essential oils. I. Production  Sterrett, Frances S.
Provides a list of essential oils and examines their methods of production.
Sterrett, Frances S. J. Chem. Educ. 1962, 39, 203.
Natural Products |
Synthesis
Inorganic Syntheses. Volume 6 (Rochow, Eugene G., ed.)  

J. Chem. Educ. 1961, 38, A552.
Synthesis
Organic syntheses. Volume 40 (Newman, Melvin S.)  Reinheimer, John D.

Reinheimer, John D. J. Chem. Educ. 1961, 38, A444.
Synthesis
Ammonia, Manufacture and Uses (Harding, A. J.)  Fornoff, Frank J.

Fornoff, Frank J. J. Chem. Educ. 1961, 38, A196.
Industrial Chemistry |
Synthesis
Letters  Smith, W. B.
The author suggests two experiments for determining the best method for preparing cyclopentanone from adipic acid.
Smith, W. B. J. Chem. Educ. 1961, 38, 638.
Aldehydes / Ketones |
Synthesis
The synthesis of diamond  Hall, H. Tracy
Examines the crystalline structure of the diamond and the chemical and industrial processes involved in its synthesis.
Hall, H. Tracy J. Chem. Educ. 1961, 38, 484.
Synthesis |
Crystals / Crystallography |
Solids |
Industrial Chemistry
Synthetic methods of organic chemistry. Volume 14 (Theilheimer, W.; Karger, S.)  Becker, Ernest I.

Becker, Ernest I. J. Chem. Educ. 1961, 38, 330.
Synthesis
PolystyreneA multistep synthesis: For the undergraduate organic chemistry laboratory  Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving
Describes a multistep synthesis in which polystyrene is synthesized from benzene.
Wilen, Samuel H.; Kremer, Chester B.; Waltcher, Irving J. Chem. Educ. 1961, 38, 304.
Polymerization |
Synthesis
Ribonucleic acid and protein synthesis  Roth, Jay S.
Examines the role of nucleic acids in protein synthesis.
Roth, Jay S. J. Chem. Educ. 1961, 38, 217.
Proteins / Peptides |
Synthesis |
Amino Acids
Recent developments in metal carbonyl synthesis  Podall, Harold E.
Reviews the historical background of simple metal carbonyls and several recent developments in their synthesis.
Podall, Harold E. J. Chem. Educ. 1961, 38, 187.
Metals |
Synthesis
Synthesis Inorganic Chemistry (Jolly, William L.)  Kauffman, George B.

Kauffman, George B. J. Chem. Educ. 1961, 38, 157.
Synthesis
Depsides: A synthesis by Emil Fischer  Ratnam, C. V.
Describes the synthesis of depsides by Emil Fischer.
Ratnam, C. V. J. Chem. Educ. 1961, 38, 93.
Synthesis |
Natural Products |
Phenols |
Mechanisms of Reactions
New vat-dyes suitable for student experiments  Shapiro, Robert; Sugerman, Gerald; Rachbach, Howard; Wagreich, Harry
Reports on the preparation of new vat-dye mixtures that can be made rapidly at room temperature suing relatively simple equipment.
Shapiro, Robert; Sugerman, Gerald; Rachbach, Howard; Wagreich, Harry J. Chem. Educ. 1960, 37, 526.
Dyes / Pigments |
Synthesis
Organic Syntheses: An Annual Publication of Satisfactory Methods for the Preparation of Organic Chemicals. Volume 39. (Tishler, Max, ed.)  Dunbar, Ralph E.

Dunbar, Ralph E. J. Chem. Educ. 1960, 37, 440.
Synthesis
Syntheses of heterocyclic compounds. Volumes 1 and 2 (Mndzhoian, A. L., ed.)  McKee, R. L.

McKee, R. L. J. Chem. Educ. 1960, 37, 274.
Heterocycles |
Synthesis
Synthetic Methods of Organic Chemistry. Volume 13 (Theilheimer, W.)  Becker, Ernest I.

Becker, Ernest I. J. Chem. Educ. 1960, 37, 218.
Synthesis
A simplified bomb for hydrothermal synthesis  Plumley, Arthur L.
Details the construction of a simplified bomb for hydrothermal synthesis.
Plumley, Arthur L. J. Chem. Educ. 1960, 37, 201.
Laboratory Equipment / Apparatus |
Calorimetry / Thermochemistry |
Synthesis
A safe method for preparation of uncontaminated hydrazoic acid  Kemp, Maryland D.
This modification eliminates the hazard of high concentrations of hydrazoic acid in the vapor phase and yields a product free of sulfate impurity.
Kemp, Maryland D. J. Chem. Educ. 1960, 37, 142.
Acids / Bases |
Synthesis
A simplified preparation of anthraquinone  Wilcox, C. R., Jr.; Stevens, M.
The cyclization of ortho-benzoylbenzoic acid to anthraquinone by strong acids is an instructive reaction for elementary organic laboratory course because it is a model of the industrial preparation of the important anthraquinone dye intermediates and serves as a point of entry into the area of polycyclic aromatic chemistry.
Wilcox, C. R., Jr.; Stevens, M. J. Chem. Educ. 1959, 36, 633.
Synthesis |
Dyes / Pigments |
Aromatic Compounds
Aniline by a modified Jones reductor method  Stubbs, U. Simpson, Jr.; Atkins, Cyril F.
By making certain simple modifications in the Jones reductor aniline can be prepared from nitrobenzene.
Stubbs, U. Simpson, Jr.; Atkins, Cyril F. J. Chem. Educ. 1959, 36, 611.
Synthesis |
Aromatic Compounds
Preparation of 2,4-dinitrophenylhydrazones: Demonstrating acid catalysis  Shine, H. J.
The use of solutions of 2,4-dinitrophenylhydrazine in the dimethyl ether of diethylene glycol enables acid catalysis to be demonstrated very easily, and also permits a comparison of catalysis between weak and strong acids.
Shine, H. J. J. Chem. Educ. 1959, 36, 575.
Acids / Bases |
Catalysis |
Synthesis
Laboratory synthesis of a heterocyclic compound  Schimelpfenig, C. W.
The authors present a procedure for the preparation of benzofurazan oxide ina test tube that requires 45 minutes and introduces students to a valuable research technique.
Schimelpfenig, C. W. J. Chem. Educ. 1959, 36, 570.
Synthesis |
Heterocycles
A new course in synthetic inorganic chemistry  Jolly, William L.
Describes a course in synthetic inorganic chemistry and its key components, including laboratory work.
Jolly, William L. J. Chem. Educ. 1959, 36, 513.
Synthesis
The preparation of barium chloranilate  Thomas, E. B.
The use of barium chloranilate in the colorimetric determination of sulfate offers an effective means of introducing classes in quantitative analysis to indirect, colorimetric procedures.
Thomas, E. B. J. Chem. Educ. 1959, 36, 383.
Qualitative Analysis |
Synthesis
Laboratory preparation of cellophane  Miller, Meredith
Offers a simplified procedure suitable for the preparation of cellophane for small-scale classroom demonstration purposes.
Miller, Meredith J. Chem. Educ. 1958, 35, 517.
Synthesis |
Polymerization
A bench-scale preparation of thioacetamide  O'Connor, William F.; Cogswell, George W.; Moriconi, Emil J.
The bench-scale preparation of thioacetamide presented is a modification of an earlier technique.
O'Connor, William F.; Cogswell, George W.; Moriconi, Emil J. J. Chem. Educ. 1958, 35, 405.
Synthesis |
Qualitative Analysis |
Aqueous Solution Chemistry
The laboratory preparation of hydrogen sulfide: A historical survey  Aynsley, E. E.; Campbell, W. A.
Examines a variety of historical methods and apparatus used in the preparation of hepatic air (hydrogen sulfide), particularly Kipp's apparatus.
Aynsley, E. E.; Campbell, W. A. J. Chem. Educ. 1958, 35, 347.
Synthesis
The small scale preparation of azobenzene and of hydrazobenzene  Vogel, A. I.; Watling, A.; Watling, J.
A satisfactory procedure for the preparation of azobenzene consists of the reduction of pure nitrobenzene with magnesium turnings and anhydrous methanol; hydrazobenzene may be prepared by reduction of nitrobenzene either with Devarda's alloy and sodium hydroxide solution or with excess of magnesium and anhydrous methanol.
Vogel, A. I.; Watling, A.; Watling, J. J. Chem. Educ. 1958, 35, 40.
Synthesis |
Aromatic Compounds
Chloramine  Drago, Russell S.
In this article, the chemistry of chloramine is reviewed by discussing its synthesis, analytical detection, structure, physical properties, and chemical reactions.
Drago, Russell S. J. Chem. Educ. 1957, 34, 541.
Amines / Ammonium Compounds |
Synthesis |
Physical Properties |
Reactions
Textbook Errors: Guest column. Arsenic(V) chloride  Dasent, W. E.
The literature on AsCl5 makes it quite clear that the substance has never been prepared.
Dasent, W. E. J. Chem. Educ. 1957, 34, 535.
Synthesis
Preparation of carbonate-free bases  Powell, Jack E.; Hiller, Maynard A.
Various methods for producing carbonate-free base to be used in titrations.
Powell, Jack E.; Hiller, Maynard A. J. Chem. Educ. 1957, 34, 330.
Acids / Bases |
Synthesis |
Titration / Volumetric Analysis |
Quantitative Analysis
Ferrocene: A novel organometallic compound  Rausch, Marvin; Vogel, Martin; Rosenberg, Harold
Examines the preparation, physical properties, structure, aromatic character, reactions, and applications of ferrocene.
Rausch, Marvin; Vogel, Martin; Rosenberg, Harold J. Chem. Educ. 1957, 34, 268.
Organometallics |
Synthesis |
Physical Properties |
Aromatic Compounds
Building a natural rubber latex compound  Button, Dale W.
Progressive development in rubber compounding have shown that enhanced properties are obtained by vulcanization with heat, by control of curing rate with accelerators and activators, and by the use of antioxidants to retard deterioration.
Button, Dale W. J. Chem. Educ. 1957, 34, 255.
Natural Products |
Synthesis |
Polymerization
Organic isocyanatesVersatile intermediates  Arnold, R. G.; Nelson, J. A.; Verbanc, J. J.
Considers reactions and the synthesis of organic isocyanates, polyisocyanates, fibers, foams, elastomers, adhesives, isocyanate generators, and plastics.
Arnold, R. G.; Nelson, J. A.; Verbanc, J. J. J. Chem. Educ. 1957, 34, 158.
Polymerization |
Synthesis |
Mechanisms of Reactions
New techniques of photochemical synthesis  McNesby, J. R.
New techniques of photochemical synthesis reviewed include the addition of free radicals to double bonds and the preparation of specifically deuterated compounds.
McNesby, J. R. J. Chem. Educ. 1957, 34, 130.
Photochemistry |
Synthesis |
Addition Reactions
Preparation of carbonyl compounds by catalytic dehydrogenation in liquid phase  Halasz, A.
Offers a procedure for the preparation of carbonyl compounds by catalytic dehydrogenation in liquid phase.
Halasz, A. J. Chem. Educ. 1956, 33, 624.
Synthesis |
Catalysis
The glycol centenary  Farber, Eduard
Describes the original synthesis of glycol by Adolphe Wurtz in 1856 and traces its subsequent production.
Farber, Eduard J. Chem. Educ. 1956, 33, 117.
Synthesis |
Alcohols
The laboratory preparation of a simple vitamin: p-aminobenzoic acid  Kremer, Chester B.
Describes the laboratory preparation of a simple vitamin, p-aminobenzoic acid, with beneficial physiological activity.
Kremer, Chester B. J. Chem. Educ. 1956, 33, 71.
Vitamins |
Synthesis
Gemesis  Reprinted from the Industrial Bulletin of Arthur D. Little, Inc.
Describes the first successful, artificial synthesis of diamonds by scientists at the General Electric Research Laboratory.
Reprinted from the Industrial Bulletin of Arthur D. Little, Inc. J. Chem. Educ. 1955, 32, 430.
Synthesis
Continuous reactors for preparing organic chemicals  Allen, C. F. H.; Byers, J. R., Jr.; Humphlett, W. J.; Reynolds, D. D.
An apparatus has been designed to circumvent the undesirable features of "batch processing" in the preparation of organic substances.
Allen, C. F. H.; Byers, J. R., Jr.; Humphlett, W. J.; Reynolds, D. D. J. Chem. Educ. 1955, 32, 394.
Synthesis |
Laboratory Equipment / Apparatus
Synthesis of copper(I) sulfide  Scholes, Samuel R., Jr.
The formation of sulfur dioxide fumes during the synthesis of copper(I) sulfide can be avoided by a simple, small-scale procedure.
Scholes, Samuel R., Jr. J. Chem. Educ. 1955, 32, 365.
Synthesis
The preparation of 2,3,6-tri-t-butylphenol  Somers, Bruce G.; Cook, Clinton D.
This preparation has been conducted by second-semester, elementary organic chemistry students with good results.
Somers, Bruce G.; Cook, Clinton D. J. Chem. Educ. 1955, 32, 312.
Synthesis |
Phenols |
Mechanisms of Reactions
A laboratory exercise in catalytic dehydrogenation  Allison, Elizabeth; Gorsich, Richard; Binder, L. O.
Presents an apparatus that uses a copper catalyst to prepare aldehydes and ketones from alcohols through catalytic dehydrogenation.
Allison, Elizabeth; Gorsich, Richard; Binder, L. O. J. Chem. Educ. 1955, 32, 209.
Catalysis |
Alcohols |
Aldehydes / Ketones |
Synthesis
A sequence of synthesis in the general organic laboratory class  Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E.
This synthesis involves the oxidation of p-xylene, nitration and esterfication of terephthalic acid, reduction of nitroterephthalic acid, and the preparation of 4-quinazolone-7-carboxylic acid.
Lange, Erwin F.; Teranishi, Roy; Christensen, Bert E. J. Chem. Educ. 1955, 32, 40.
Synthesis |
Aromatic Compounds |
Reactions |
Oxidation / Reduction
Preparation of anhydrous pyridine hydrochloride  Taylor, Moddie D.; Grant, Louis R.
Describes the preparation of anhydrous pyridine hydrochloride.
Taylor, Moddie D.; Grant, Louis R. J. Chem. Educ. 1955, 32, 39.
Synthesis
New salts of para-xylene sulfonic acid  Mangold, Sister M. Clarita; Weber, Rosemary; Williams, Constance
Reports on several new salts of para-xylene sulfonic acid produced as a part of a senior research project.
Mangold, Sister M. Clarita; Weber, Rosemary; Williams, Constance J. Chem. Educ. 1954, 31, 644.
Undergraduate Research |
Synthesis
A synthesis of bis(p-aminophenyl) sulfone for laboratory classes  Buckles, Robert E.
A three-step synthesis of bis(p-aminophenyl) sulfone from p-chloronitrobenzene has been devised on a fairly small scale for laboratory classes in beginning organic chemistry.
Buckles, Robert E. J. Chem. Educ. 1954, 31, 36.
Synthesis |
Aldehydes / Ketones
Preparation of 2-naphthaldehyde  Doukas, Harry M.
Describes an improved procedure for the preparation of 2-naphthaldehyde.
Doukas, Harry M. J. Chem. Educ. 1954, 31, 12.
Aldehydes / Ketones |
Synthesis
The preparation of ninhydrin as a laboratory experiment  Dominguez, Xorge Alejandro
The preparation of ninhydrin, a useful but expensive colorimetric reagent, can be accomplished easily in three laboratory sessions.
Dominguez, Xorge Alejandro J. Chem. Educ. 1953, 30, 624.
Synthesis |
Mechanisms of Reactions
A secondary-school course in inorganic preparations  Weaver, Elbert C.
Describes a secondary-school course in inorganic preparations designed to keep chemistry bright and interesting for later use in college courses.
Weaver, Elbert C. J. Chem. Educ. 1953, 30, 386.
Synthesis
The Fischer indole synthesis  Roussel, Philip A.
Examines the discovery of indole and Fischer's work to develop a means of its synthesis.
Roussel, Philip A. J. Chem. Educ. 1953, 30, 122.
Synthesis |
Mechanisms of Reactions |
Molecular Properties / Structure |
Aromatic Compounds
A course in inorganic preparations  Gayer, Karl H.; Elkind, Michael J.
Describes a senior course in preparative inorganic chemistry at Wayne University and includes references, suggested syntheses, and typical assignments.
Gayer, Karl H.; Elkind, Michael J. J. Chem. Educ. 1953, 30, 90.
Synthesis
The Friedel-Crafts reaction in elementary organic laboratories  Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl
Presents a modification of the Perrier ketone synthesis.
Wright, Oscar L.; Fuhlhage, Donald; Sheridan, Earl J. Chem. Educ. 1952, 29, 620.
Reactions |
Aldehydes / Ketones |
Synthesis
Letters  Hendricks, B. Clifford
The author elaborates on the value of syntheses in the instructional laboratory.
Hendricks, B. Clifford J. Chem. Educ. 1952, 29, 582.
Synthesis
A simple procedure for preparing pinacol hydrate  Weber, Joseph E.; Boggs, Arlo D.
Presents a simple procedure for preparing pinacol hydrate.
Weber, Joseph E.; Boggs, Arlo D. J. Chem. Educ. 1952, 29, 363.
Synthesis
Peter Griess and the phenylene diamines  Smith, Manning A.; Gower, William R.
Contrary to the claim made by some textbooks, Peter Griess did not isolate and decarboxylate the six diaminobenzooic acids.
Smith, Manning A.; Gower, William R. J. Chem. Educ. 1952, 29, 176.
Amines / Ammonium Compounds |
Aromatic Compounds |
Synthesis |
Molecular Properties / Structure
Laboratory synthesis in general freshman chemistry  Holtzclaw, Henry F., Jr.
The author has found that experiments requiring syntheses of compounds stimulate the interest of students remarkably and provides them with much valuable laboratory experience.
Holtzclaw, Henry F., Jr. J. Chem. Educ. 1952, 29, 95.
Synthesis
A simple preparation of primary-standard sodium chloride  Meites, Louis
This paper describes a method for the purification of sodium chloride that gives a 70 to 80 percent yield with an effective purity of 100 +/- 0.01 percent.
Meites, Louis J. Chem. Educ. 1952, 29, 74.
Synthesis
The story of barbituric acid  Carter, Mary Kathleen
Describes the relationships between the synthetic work of several chemists that led to the production of barbituric acid by Baeyer in 1864.
Carter, Mary Kathleen J. Chem. Educ. 1951, 28, 524.
Acids / Bases |
Synthesis
The preparation of "2-bromo-naphthalene"  Wolfe, Winthrop C.; Doukas, Harry M.
Presents a procedure for the preparation of "2-bromo-naphthalene" in large or small amounts.
Wolfe, Winthrop C.; Doukas, Harry M. J. Chem. Educ. 1951, 28, 472.
Synthesis |
Alkenes
Experiments with cyclopentadiene  Wagner, E. C.; Hunt, William C.
The experiments outlined here serve to illustrate the processes of polymerization and depolymerization, the Diels-Alder reaction, and the presence of a reactive methylene group in cyclopentadiene.
Wagner, E. C.; Hunt, William C. J. Chem. Educ. 1951, 28, 309.
Alkenes |
Synthesis |
Polymerization
A simple method for the preparation of tertiary amines  Butler, George B.; Benjamin, Ben M.
Describes a simple method for the preparation of tertiary amines.
Butler, George B.; Benjamin, Ben M. J. Chem. Educ. 1951, 28, 191.
Amines / Ammonium Compounds |
Synthesis
A new derivative for the identification of primary aromatic amines  Lappin, Gerald R.
Describe an investigation into the products reactions between various primary aromatic amines and ethyl ethoxymethylenemalonate as a means of identifying primary aromatic amines.
Lappin, Gerald R. J. Chem. Educ. 1951, 28, 126.
Qualitative Analysis |
Aromatic Compounds |
Amines / Ammonium Compounds |
Heterocycles |
Synthesis