TIGER

Journal Articles: 125 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
Synthesis of Albendazole Metabolite: Characterization and HPLC Determination  Graciela Mahler, Danilo Davyt, Sandra Gordon, Marcelo Incerti, Ivana Núñez, Horacio Pezaroglo, Laura Scarone, Gloria Serra, Mauricio Silvera, and Eduardo Manta
In this laboratory activity, students are introduced to the synthesis of an albendazole metabolite obtained by a sulfide oxidation reaction. Albendazole as well as its metabolite, albendazole sulfoxide, are used as anthelmintic drugs. The oxidation reagent is H2O2 in acetic acid. The reaction is environmental friendly, fast, and proceeds with high yield. The crude reaction is analyzed by HPLC chromatography to determine purity. The simplicity of the experiment allows students to study chiral concepts, physicochemical and spectroscopic properties of the compounds, and HPLC determinations.
Mahler, Graciela; Davyt, Danilo; Gordon, Sandra; Incerti, Marcelo; Núñez, Ivana; Pezaroglo, Horacio; Scarone, Laura; Serra, Gloria; Silvera, Mauricio; Manta, Eduardo. J. Chem. Educ. 2008, 85, 1652.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
HPLC |
Medicinal Chemistry |
Organosulfur Compounds |
Oxidation / Reduction |
Synthesis
Experimental Design and Optimization: Application to a Grignard Reaction  Naoual Bouzidi and Christel Gozzi
This 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.
Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ. 2008, 85, 1544.
Addition Reactions |
Alcohols |
Aldehydes / Ketones |
Chemometrics |
Gas Chromatography |
Organometallics |
Synthesis
The Synthesis of N-Benzyl-2-azanorbornene via Aqueous Hetero Diels–Alder Reaction  Xavier Sauvage and Lionel Delaude
Characterization of the product of this organic synthesis through IR and NMR data analysis provides valuable material to familiarize students with different types of protonproton coupling patterns and their typical ranges, serves to illustrate the concepts of green chemistry and atom efficiency, and can be used to exemplify structural analysis and computational studies.
Sauvage, Xavier; Delaude, Lionel. J. Chem. Educ. 2008, 85, 1538.
Alkenes |
Aqueous Solution Chemistry |
Conformational Analysis |
Green Chemistry |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
Stereochemistry |
Synthesis
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye  Cheryl M. Mascarenhas
In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.
Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1271.
Alcohols |
Aromatic Compounds |
Dyes / Pigments |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
The Preparation and Enzymatic Hydrolysis of a Library of Esters  Elizabeth M. Sanford and Traci L. Smith
In this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.
Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ. 2008, 85, 944.
Drugs / Pharmaceuticals |
Enzymes |
Esters |
Industrial Chemistry |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
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
Determination of Hammett Equation Rho Constant for the Hydrolysis of p-Nitrophenyl Benzoate Esters  Sheue L. Keenan, Karl P. Peterson, Kelly Peterson, and Kyle Jacobson
In this experiment, seven p-nitrophenyl benzoate esters are synthesized and characterized. Students then measure the rate constants for the base hydrolysis of these esters using UV-vis spectrophotometry and determine the Hammett equation constant for this hydrolysis reaction.
Keenan, Sheue L.; Peterson, Karl P.; Peterson, Kelly; Jacobson, Kyle. J. Chem. Educ. 2008, 85, 558.
Aromatic Compounds |
Esters |
IR Spectroscopy |
Kinetics |
Synthesis |
UV-Vis Spectroscopy
Converting Municipal Waste into Automobile Fuel: Ethanol from Newspaper  Mark Mascal and Richard Scown
In this experiment, waste newspaper is pulped with acid and its cellulose hydrolyzed to produce glucose syrup that is fermented and distilled to yield ethanol. In doing so, students are introduced to carbohydrate chemistry and the use of fermentation in organic synthesis.
Mascal, Mark; Scown, Richard. J. Chem. Educ. 2008, 85, 546.
Acids / Bases |
Alcohols |
Applications of Chemistry |
Biotechnology |
Carbohydrates |
Qualitative Analysis |
Synthesis |
Thin Layer Chromatography
A Simple Method for Drawing Chiral Mononuclear Octahedral Metal Complexes  Aminou Mohamadou and Arnaud Haudrechy
This article presents a simple and progressive method to draw all of the octahedral complexes of coordination units with at least two different monodentate ligands and show their chiral properties.
Mohamadou, Aminou; Haudrechy, Arnaud. J. Chem. Educ. 2008, 85, 436.
Asymmetric Synthesis |
Chirality / Optical Activity |
Coordination Compounds |
Diastereomers |
Enantiomers |
Molecular Properties / Structure |
Stereochemistry |
Transition Elements
Synthesis and Characterization of 9-Hydroxyphenalenone Using 2D NMR Techniques  Benjamin Caes and Dell Jensen Jr.
The synthesis of 9-Hydroxyphenalenone produces a planar multicyclic beta-ketoenol, the tautomerization of which results in C2v symmetry on the NMR time scale, thus simplifying the spectra and providing a unique structure for teaching 2D NMR spectroscopy.
Caes, Benjamin; Jensen, Dell, Jr. J. Chem. Educ. 2008, 85, 413.
Alcohols |
Aldehydes / Ketones |
Aromatic Compounds |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis
Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-Methylstyrene  Brad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. Murphy
In the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition.
Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ. 2008, 85, 102.
Addition Reactions |
Alcohols |
Alkenes |
Constitutional Isomers |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
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
Microwave-Assisted Organic Synthesis in the Organic Teaching Lab: A Simple, Greener Wittig Reaction  Eric Martin and Cynthia Kellen-Yuen
A microwave-assisted Wittig reaction has been developed for the organic teaching laboratory. Utilizing this technique, a variety of styrene derivatives have been synthesized from aromatic aldehydes in good yields. The mixture of cis and trans alkenes produced also provides instructors with opportunities to emphasize the spectroscopic analysis of product mixtures.
Martin, Eric; Kellen-Yuen, Cynthia. J. Chem. Educ. 2007, 84, 2004.
Aldehydes / Ketones |
Alkenes |
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Spectroscopy |
Synthesis
A Knoevenagel Initiated Annulation Reaction Using Room Temperature or Microwave Conditions  A. Gilbert Cook
The product of a Knoevenagel initiated annulation reaction is identified through a guided prelab exercise of the synthesis of the Hagemann ester, and then through the analysis of GCMS, NMR, and IR spectra. The stereochemistry of the product is determined through the NMR spectrum and Karplus curve, and the student is required to write a mechanism for the reaction.
Cook, A. Gilbert. J. Chem. Educ. 2007, 84, 1477.
Aldehydes / Ketones |
Conformational Analysis |
Gas Chromatography |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
NMR Spectroscopy |
Stereochemistry |
Synthesis
Using a Premade Grignard Reagent To Synthesize Tertiary Alcohols in a Convenient Investigative Organic Laboratory Experiment  Michael A. G. Berg and Roy D. Pointer
Describes the use of a commercially available Grignard reagent in a Grignard synthesis that avoided the failures typically associated with the Grignard reaction.
Berg, Michael A. G.; Pointer, Roy D. J. Chem. Educ. 2007, 84, 483.
Aldehydes / Ketones |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Organometallics |
Synthesis
A Green Enantioselective Aldol Condensation for the Undergraduate Organic Laboratory  George D. Bennett
The proline-catalyzed aldol condensation between acetone and isobutyraldehyde proceeds in good yield and with high enantioselectivity at room temperature. This multi-week experiment also illustrates a number of principles and trade-offs of green chemistry.
Bennett, George D. J. Chem. Educ. 2006, 83, 1871.
Addition Reactions |
Aldehydes / Ketones |
Asymmetric Synthesis |
Catalysis |
Chirality / Optical Activity |
Green Chemistry |
Mechanisms of Reactions |
Stereochemistry
Keeping Your Students Awake: Facile Microscale Synthesis of Modafinil, a Modern Anti-Narcoleptic Drug  Evangelos Aktoudianakis, Rui Jun Lin, and Andrew P. Dicks
Describes the microscale preparation of modafinil, a pharmaceutical recently approved for the treatment of narcolepsy, by a sulfide oxidation reaction. An unusual feature of modafinil is the presence of a chiral sulfoxide functionality where a sulfur atom acts as a stereocenter, demonstrating that atoms other than carbon can act as centers of chirality.
Aktoudianakis, Evangelos; Lin, Rui Jun; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 1832.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Synthesis |
Mechanisms of Reactions |
IR Spectroscopy |
NMR Spectroscopy |
Microscale Lab |
Stereochemistry
Microwave-Mediated Synthesis of Lophine: Developing a Mechanism To Explain a Product   R. David Crouch, Jessica L. Howard, Jennifer L. Zile, and Kathryn H. Barker
Describes the microwave-mediated preparation of lophine (2,4,5-triphenylimidazole). The experiment also provides an opportunity for students to employ the principles of carbonyl chemistry in devising a mechanism to explain the formation of the product.
Crouch, R. David; Howard, Jessica L.; Zile, Jennifer L.; Barker, Kathryn H. J. Chem. Educ. 2006, 83, 1658.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Aromatic Compounds |
Microscale Lab |
Molecular Modeling |
Synthesis |
NMR Spectroscopy
Developing Critical Thinking Skills: The "Sabotaged" Synthesis of Methyl p-Bromobenzoate  Eric J. Mahan and Mary Alice Nading
Before beginning an experiment, students are told that someone might have sabotaged their experiment to produce other-than-expected results. The objective is to perform the experiment, determine if any sabotage has occurred, and, if so, identify the changes that were made to the reagents as well as the person responsible.
Mahan, Eric J.; Nading, Mary Alice. J. Chem. Educ. 2006, 83, 1652.
Alcohols |
Carboxylic Acids |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis
The Step-by-Step Robinson Annulation of Chalcone and Ethyl Acetoacetate. An Advanced Undergraduate Project in Organic Synthesis and Structural Analysis  Lionel Delaude, Jean Grandjean, and Alfred F. Noels
The Robinson annulation is a three-step process involving a Michael addition followed by an internal aldol condensation and a dehydration. It is possible to stop the reaction after every step and to isolate the three products, allowing students to confirm the validity of the stepwise mechanism and develop a more thorough understanding of the whole process.
Delaude, Lionel; Grandjean, Jean; Noels, Alfred F. J. Chem. Educ. 2006, 83, 1225.
Catalysis |
Chirality / Optical Activity |
Conformational Analysis |
Diastereomers |
IR Spectroscopy |
Synthesis |
NMR Spectroscopy |
Stereochemistry
Regiospecific Epoxidation of Carvone: A Discovery-Oriented Experiment for Understanding the Selectivity and Mechanism of Epoxidation Reactions  Kendrew K. W. Mak, Y. M. Lai, and Yuk-Hong Siu
Peroxy acids and alkaline H2O2 are two commonly used reagents for alkene epoxidation. The former react preferentially with electron-rich alkenes while the latter works better with a,-unsaturated carbonyl compounds. The selectivity of these two reagents on carvone, a naturally occurring compound that contains both types of C=C bonds, is investigated.
Mak, Kendrew K. W.; Lai, Y. M.; Siu, Yuk-Hong. J. Chem. Educ. 2006, 83, 1058.
Alkenes |
Chromatography |
Epoxides |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Mechanisms of Reactions
Evaluating the Internal Charge-Transfer in Benzylidene Derivatives of N,N′-Dimethylbarbituric Acid  Marcos Caroli Rezende, Francisco Jara, and Moisés Domínguez
Four benzylidene derivatives of N,N'-dimethylbarbituric acid are prepared and their UVvisible and 1H NMR spectra used to characterize the molecular internal charge-transfer in the molecules.
Rezende, Marcos Caroli; Jara, Francisco; Domínguez, Moisés. J. Chem. Educ. 2006, 83, 937.
Aqueous Solution Chemistry |
Aromatic Compounds |
Dyes / Pigments |
Molecular Properties / Structure |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
Acetal Protecting Groups in the Organic Laboratory: Synthesis of Methyl 4,6-O-Benzylidene-α-D-Glucopyranoside  Alexei V. Demchenko, Papapida Pornsuriyasak, and Cristina De Meo
The synthesis of methyl 4,6-O-benzylidene-a-D-glucopyranoside provides an opportunity to synthesize a cyclic acetal; stereoselectively introduce a chirality center; and learn extraction, evaporation, precipitation, optical rotation, melting point measurement, thin-layer chromatography, IR-spectroscopy, mass spectrometry, and various NMR techniques.
Demchenko, Alexei V.; Pornsuriyasak, Papapida; De Meo, Cristina. J. Chem. Educ. 2006, 83, 782.
Carbohydrates |
IR Spectroscopy |
Medicinal Chemistry |
NMR Spectroscopy |
Thin Layer Chromatography |
Synthesis
The Amazingly Versatile Titanocene Derivatives  Donald C. Bowman
Derivatives of titanocene are remarkably versatile in their chemical applications. This article presents a brief review of the derivatives' uses in the fields of polymers, medical oncology, and organic synthesis.
Bowman, Donald C. J. Chem. Educ. 2006, 83, 735.
Applications of Chemistry |
Catalysis |
Drugs / Pharmaceuticals |
Organometallics |
Polymerization |
Synthesis
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
A Greener Approach to Aspirin Synthesis Using Microwave Irradiation  Ingrid Montes, David Sanabria, Marilyn García,, Joaudimir Castro, and Johanna Fajardo
Presents an inquiry-based laboratory experience based on the use of a microwave oven as a means for a comparative study of the effect of different catalysts in the synthesis of aspirin.
Montes, Ingrid; Sanabria, David; García,, Marilyn; Castro, Joaudimir; Fajardo, Johanna. J. Chem. Educ. 2006, 83, 628.
Drugs / Pharmaceuticals |
Esters |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis |
Thin Layer Chromatography
Synthesis of Methyl Diantilis, a Commercially Important Fragrance  William H. Miles and Katelyn B. Connell
Describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws.
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
Alcohols |
Food Science |
Catalysis |
Ethers |
Industrial Chemistry |
IR Spectroscopy |
Lewis Acids / Bases |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
Grubbs's Cross Metathesis of Eugenol with cis-2-Butene-1,4-diol To Make a Natural Product. An Organometallic Experiment for the Undergraduate Lab   Douglass F. Taber and Kevin J. Frankowski
Describes the ruthenium catalyzed cross metathesis of eugenol with cis-1,4-butenediol. The experiment is an excellent example of the powerful selectivity possible with the Grubbs' catalyst, demonstrating the preference for trans over cis alkene formation and for cross metathesis over homodimerization.
Taber, Douglass F.; Frankowski, Kevin J. J. Chem. Educ. 2006, 83, 283.
Alkenes |
Catalysis |
IR Spectroscopy |
Mass Spectrometry |
Mechanisms of Reactions |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Organometallics |
Stereochemistry |
Synthesis |
Thin Layer Chromatography |
Transition Elements
Diastereoselectivity in the Reduction of α-Hydroxyketones. An Experiment for the Chemistry Major Organic Laboratory  David B. Ball
Describes a research type, inquiry-based project where students synthesize racemic ahydroxyketones using umpolung, a polarity-reversal approach; investigate chelating versus non-chelating reducing agents; and determine the diastereoselectivity of these reducing processes by NMR spectroscopy.
Ball, David B. J. Chem. Educ. 2006, 83, 101.
Addition Reactions |
Aldehydes / Ketones |
Chirality / Optical Activity |
Chromatography |
Conferences |
Constitutional Isomers |
Enantiomers |
NMR Spectroscopy |
Stereochemistry |
Synthesis |
Conformational Analysis
Fluorous Compounds and Their Role in Separation Chemistry  Maria Angeles Ubeda and Roman Dembinski
Reviews fluorous technology and outlines strategies towards organic synthesis.
Ubeda, Maria Angeles; Dembinski, Roman. J. Chem. Educ. 2006, 83, 84.
Amino Acids |
Catalysis |
Esters |
Green Chemistry |
Separation Science |
Synthesis
Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal Acetylenes  William D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. Lindberg
In keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.
Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ. 2005, 82, 1833.
Catalysis |
Heterocycles |
Alkynes |
IR Spectroscopy |
NMR Spectroscopy |
Reactions |
Thin Layer Chromatography |
Synthesis
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
The Virtual ChemLab Project: A Realistic and Sophisticated Simulation of Organic Synthesis and Organic Qualitative Analysis  Brian F. Woodfield, Merritt B. Andrus, Gregory L. Waddoups, Melissa S. Moore, Richard Swan, Rob Allen, Greg Bodily, Tricia Andersen, Jordan Miller, Bryon Simmons, and Richard Stanger
Describes a set of sophisticated and realistic laboratory simulations for use in freshman- and sophomore-level chemistry classes and laboratories called Virtual ChemLab. The purpose of these simulations is to reinforce concepts taught in the classroom, provide an environment for creative learning, and emphasize the thinking behind instructional laboratory experiments.
Woodfield, Brian F.; Andrus, Merritt B.; Waddoups, Gregory L.; Moore, Melissa S.; Swan, Richard; Allen, Rob; Bodily, Greg; Andersen, Tricia; Miller, Jordan; Simmons, Bryon; Stanger, Richard. J. Chem. Educ. 2005, 82, 1728.
IR Spectroscopy |
NMR Spectroscopy |
Qualitative Analysis |
Synthesis |
Reactions |
Thin Layer Chromatography
Conversion of an Aziridine to an Oxazolidinone Using a Salt and Carbon Dioxide in Water  Justin R. Wallace, Deborah L. Lieberman, Matthew T. Hancock, and Allan R. Pinhas
An undergraduate laboratory experiment that allows for optimization of experimental reaction conditions for the conversion of a readily-available aziridine to the corresponding oxazolidinone using only carbon dioxide and a salt in water is discussed. A variety of salts were used to determine their effect on the reaction. In all cases, either no reaction occurred or a high yield of product was obtained. Ring opening of the less substituted carbonnitrogen bond predominates. This experiment allows students to optimize reaction conditions to obtain predominantly one of two regioisomers.
Wallace, Justin R.; Lieberman, Deborah L.; Hancock, Matthew T.; Pinhas, Allan R. J. Chem. Educ. 2005, 82, 1229.
Heterocycles |
Synthesis |
Aqueous Solution Chemistry |
Constitutional Isomers |
Mechanisms of Reactions |
NMR Spectroscopy |
Quantitative Analysis
Capillary Electrophoresis Analysis of Substituted Benzoic Acids. An Experiment for the Organic Synthesis Laboratory  Nancy S. Mills, John D. Spence, and Michelle M. Bushey
We have introduced an experiment into the organic chemistry sequence, in the synthesis laboratory, that utilizes capillary electrophoresis to evaluate the pKa shift on a series of student-prepared substituted benzoic acids. The pKa shift is examined in reference to the electrophoretic-migration behavior of benzoic acid and is a result of the electron-withdrawing or electron-donating characteristics of the substituent. This strategy allows us to increase the exposure of students to modern methods of separation. We are using repeated exposure to increase students' knowledge of separation strategies and techniques.
Mills, Nancy S.; Spence, John D.; Bushey, Michelle M. J. Chem. Educ. 2005, 82, 1226.
Synthesis |
Electrophoresis |
Grignard Reagents |
Instrumental Methods |
Separation Science
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
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
Two-Step Semi-Microscale Preparation of a Cinnamate Ester Sunscreen Analog  Ryan G. Stabile and Andrew P. Dicks
The two-step synthesis and characterization of a sunscreen analog (ethyl trans-4-methoxycinnamate) is presented. This experiment is tailored towards students with a sound theoretical understanding of organic chemistry and related laboratory techniques. Appropriate synthetic discussion topics include carbonyl condensation reactions, carboxylic acid esterifications, and the so-called "cesium effect" in organic synthesis.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2004, 81, 1488.
Conductivity |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy |
Consumer Chemistry
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
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
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
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
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
Modern Projects in Organic Chemistry: Miniscale and Standard Taper Microscale, 2nd Edition (Jerry R. Mohrig, Christina Noring Hammond, Paul F. Schatz, and Terence C. Morrill)  Richard Pagni
Modern Projects and Experiments in Organic Chemistry comes in two closely related versions, one for miniscale and standard taper microscale and the other for miniscale and Williamson microscale, in conjunction with the authors techniques in organic chemistry book.
Pagni, Richard. J. Chem. Educ. 2004, 81, 649.
Chromatography |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
NMR Spectroscopy |
Physical Properties |
Synthesis
Microscale Synthesis of 1-Bromo-3-chloro-5-iodobenzene: An Improved Deamination of 4-Bromo-2-chloro-6-iodoaniline  Michael W. Pelter, Libbie S.W. Pelter, Dusanka Colovic, and Regina Strug
Overall, we find this procedure to be advantageous to the published methods owing to its requirement of less starting material, higher product yields, and a greatly simplified procedure.
Pelter, Michael W.; Pelter, Libbie S.W.; Colovic, Dusanka; Strug, Regina. J. Chem. Educ. 2004, 81, 111.
Microscale Lab |
Synthesis |
Aromatic Compounds |
Amines / Ammonium Compounds
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
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
The Chemistry of Fragrances: A Group Exercise for Chemistry Students  Roger Duprey, Charles S. Sell, and Nigel D. Lowe
Description of the Fragrance structured learning package (SLP), developed by the Department of Chemistry at the University of York to illustrate the roles of professional chemists in industrial organizations.
Duprey, Roger; Sell, Charles S.; Lowe, Nigel D. J. Chem. Educ. 2003, 80, 513.
Consumer Chemistry |
Industrial Chemistry |
Synthesis |
Student / Career Counseling |
Applications of Chemistry
Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets  Ryan G. Stabile and Andrew P. Dicks
Procedure for synthesis of the active ingredient in many well-known, over-the-counter cough syrups - 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 313.
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Mathematics / Symbolic Mathematics |
Microscale Lab |
Synthesis |
Stereochemistry |
Applications of Chemistry |
Ethers |
Aromatic Compounds |
Medicinal Chemistry
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
Preparing Students for Research: Synthesis of Substituted Chalcones as a Comprehensive Guided-Inquiry Experience  James R. Vyvyan, Donald L. Pavia, Gary M. Lampman, and George S. Kriz Jr.
An aldol condensation of substituted benzaldehydes with substituted acetophones to produce substituted benzalacetophenones (chalcones) in a guided-inquiry approach.
Vyvyan, James R.; Pavia, Donald L.; Lampman, Gary M.; Kriz, George S., Jr. J. Chem. Educ. 2002, 79, 1119.
Medicinal Chemistry |
Microscale Lab |
Natural Products |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Aldehydes / Ketones
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
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
Discovery-Oriented Approach To Organic Synthesis: Tandem Aldol Condensation-Michael Addition Reactions. Identifying Diastereotopic Hydrogens in an Achiral Molecule by NMR Spectroscopy  Nanette Wachter-Jurcsak and Kendra Reddin
Procedure illustrating aldol condensation and Michael addition reactions.
Wachter-Jurcsak, Nanette; Reddin, Kendra. J. Chem. Educ. 2001, 78, 1264.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Aromatic Compounds |
Aldehydes / Ketones |
Addition Reactions |
Mechanisms of Reactions
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
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
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
The Heck Reaction: A Microscale Synthesis Using a Palladium Catalyst  William B. Martin and Laura J. Kateley
The microscale synthesis described uses a reaction between a bromoiodobenzene and acrylic acid to produce a bromocinnamic acid. Structure verification for the product uses IR and 1H NMR spectroscopy.
Martin, William B.; Kateley, Laura J. J. Chem. Educ. 2000, 77, 757.
Catalysis |
Microscale Lab |
Synthesis |
IR Spectroscopy |
NMR Spectroscopy |
Aromatic Compounds |
Mechanisms of Reactions
Enantiomeric and Diastereoisomeric Relationships: A Practical Approach  V. Durieu, G. Martiat, M. Ch. Vandergeten, F. Pirsoul, F. Toubeau, and Agnès Van Camp
An experiment in organic chemistry in which the students prepare, purify, and characterize optical isomers. The three optical isomers of the bisoxalamides obtained by the reaction of racemic 1-phenylethylamine with diethyloxalate are separable by flash chromatography into the racemic mixture of (R,R) + (S,S) oxalamides and the (R,S) meso compound.
Durieu, V.; Martiat, G.; Vandergeten, M. Ch.; Pirsoul, F.; Toubeau, F.; Van Camp, Agnès. J. Chem. Educ. 2000, 77, 752.
Molecular Properties / Structure |
Stereochemistry |
Separation Science |
Enantiomers |
Diastereomers |
Chirality / Optical Activity |
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
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
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
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
Synthesis and Structure-Property Relationships in (h6-Arene)Cr(CO)3 Chemistry: From Guided Experiments to Discovery Research  Allen D. Hunter, Larry J. Bianconi, Steven J. DiMuzio, and Dianne L. Braho
Since instructors can have each student prepare a different complex, they are ideal targets for student directed "discovery research" lab projects. Teams of students can compare how their syntheses and the physical, spectroscopic, and electrochemical properties of their products vary as a function of the arenes' structures.
Hunter, Allen D.; Bianconi, Larry J.; DiMuzio, Steven J.; Braho, Dianne L. J. Chem. Educ. 1998, 75, 891.
Microscale Lab |
Organometallics |
IR Spectroscopy |
NMR Spectroscopy |
Electrochemistry |
Synthesis |
Coordination Compounds
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
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
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
Tactics of Organic Synthesis (Ho, Tse-Lok)  
Monograph.
J. Chem. Educ. 1995, 72, A19.
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
A phase transfer catalyzed permanganate oxidation: preparation of vanillin from isoeugenol acetate  Lampman, Gary M.; Sharpe, Steven D.
There are several attractive features in this reaction sequence for the undergraduate laboratory. These include (1) use of a protecting acetate group, (2) use of a familiar "textbook" oxidant, potassium permanganate, (3) use of phase transfer catalyst, (4) preparing of an aldehyde, (5) short reaction period, and (6) the laboratory has a pleasant aroma.
Lampman, Gary M.; Sharpe, Steven D. J. Chem. Educ. 1983, 60, 503.
Oxidation / Reduction |
Catalysis |
Natural Products |
Synthesis |
Aldehydes / Ketones |
Alcohols |
Aromatic Compounds
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
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
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
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
A student synthesis of the housefly sex attractant  Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard
This multi-step synthetic sequence illustrates several important laboratory techniques, including ir and nmr spectroscopy, thin-layer and column chromatography, rotary evaporation, recrystallization, and vacuum distillation.
Cormier, Russell A.; Duc Phan, M.; Graddis, Thomas; Singer, Richard J. Chem. Educ. 1979, 56, 345.
Synthesis |
Natural Products |
IR Spectroscopy |
NMR Spectroscopy |
Chromatography |
Thin Layer Chromatography
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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