TIGER

Journal Articles: 435 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
Cocrystal Controlled Solid-State Synthesis  Miranda L. Cheney, Michael J. Zaworotko, Steve Beaton, and Robert D. Singer
Describes experiments that can easily be adapted to a typical undergraduate organic chemistry course and are inexpensive, relatively safe, require little or no solvent, have high atom economy, make use of non-toxic or low toxicity compounds, and generate negligible quantities of waste.
Cheney, Miranda L.; Zaworotko, Michael J.; Beaton, Steve; Singer, Robert D. J. Chem. Educ. 2008, 85, 1649.
Amines / Ammonium Compounds |
Calorimetry / Thermochemistry |
Green Chemistry |
IR Spectroscopy |
Microscale Lab |
Solid State Chemistry |
Synthesis
The Synthesis of a Cockroach Pheromone  Patty L. Feist
This paper describes the synthesis of gentisyl quinone isovalerate or blattellaquinone, a sex pheromone of the German cockroach and a compound with real-world applications. The experiment also affords students practice in extraction as well as IR and NMR spectroscopy.
Feist, Patty L. J. Chem. Educ. 2008, 85, 1548.
Esters |
IR Spectroscopy |
Natural Products |
NMR Spectroscopy |
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
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
A Green, Guided-Inquiry Based Electrophilic Aromatic Substitution for the Organic Chemistry Laboratory  Eric Eby and S. Todd Deal
This alternative, electrophilic aromatic substitutionan iodination reaction of salicylamide, a popular analgesicuses environmentally friendly reagents and serves as a guided-inquiry experiment in which students are asked to predict the orientation of the substitution reaction and determine the product's structure using FT-IR spectroscopy.
Eby, Eric; Deal, S. Todd. J. Chem. Educ. 2008, 85, 1426.
Aromatic Compounds |
Constitutional Isomers |
Electrophilic Substitution |
Green Chemistry |
IR Spectroscopy |
Synthesis
Synthesis of the Commercial Antidepressant Moclobemide   Jesse D. More
Describes an experiment for the undergraduate organic chemistry laboratory in which students synthesize the commercial antidepressant drug moclobemide, marketed under the trade name Manerix, in one step using commercially available material. The purity and identity of the product are confirmed by melting point and NMR and IR spectroscopy.
More, Jesse D. J. Chem. Educ. 2008, 85, 1424.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Medicinal Chemistry |
NMR Spectroscopy |
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
Frank Westheimer's Early Demonstration of Enzymatic Specificity  Addison Ault
Reviews one of the most significant accomplishments of one of the most respected chemists of the 20th centurya series of stereospecific enzymatic oxidation and reduction experiments that led chemists to recognize enantiotopic and diastereotopic relationships of atoms, or groups of atoms, within molecules.
Ault, Addison. J. Chem. Educ. 2008, 85, 1246.
Asymmetric Synthesis |
Bioorganic Chemistry |
Catalysis |
Chirality / Optical Activity |
Enantiomers |
Enzymes |
Isotopes |
Nucleophilic Substitution |
Oxidation / Reduction |
Stereochemistry
Construction of a Polyaniline Nanofiber Gas Sensor  Shabnam Virji, Bruce H. Weiller, Jiaxing Huang, Richard Blair, Heather Shepherd, Tanya Faltens, Philip C. Haussmann, Richard B. Kaner, and Sarah H. Tolbert
The objectives of this lab are to synthesize different diameter polyaniline nanofibers and compare them as sensor materials. Its advantages include simplicity and low cost, making it suitable for both high school and college students, particularly in departments with modest means.
Virji, Shabnam; Weiller, Bruce H.; Huang, Jiaxing; Blair, Richard; Shepherd, Heather; Faltens, Tanya; Haussmann, Philip C.; Kaner, Richard B.; Tolbert, Sarah H. J. Chem. Educ. 2008, 85, 1102.
Acids / Bases |
Aromatic Compounds |
Conductivity |
Hydrogen Bonding |
Oxidation / Reduction |
Oxidation State |
pH |
Polymerization |
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
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
The Baeyer–Villiger Oxidation with Trifluoroacetic Acid and Household Sodium Percarbonate  Richard A. Kjonaas and Anthony E. Clemons
Reports a method for carrying out the BaeyerVilliger oxidation of cyclopentanone to d-valerolactone in a large-section introductory organic chemistry laboratory course.
Kjonaas, Richard A.; Clemons, Anthony E. J. Chem. Educ. 2008, 85, 827.
Aldehydes / Ketones |
Esters |
NMR Spectroscopy |
Oxidation / Reduction |
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
Pyrolysis of Aryl Sulfonate Esters in the Absence of Solvent: E1 or E2? A Puzzle for the Organic Laboratory  John J. Nash, Marnie A. Leininger, and Kurt Keyes
An aryl sulfonate ester is synthesized and then pyrolyzed at reduced pressure. The volatile products are analyzed using gas chromatography to determine whether the thermal decomposition occurs via an E1 or E2 mechanism.
Nash, John J.; Leininger, Marnie A.; Keyes, Kurt . J. Chem. Educ. 2008, 85, 552.
Alkenes |
Carbocations |
Elimination Reactions |
Gas Chromatography |
Mechanisms of Reactions |
Synthesis
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
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 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
Acylation of Ferrocene: A Greener Approach  Kurt R. Birdwhistell, Andy Nguyen, Eric J. Ramos, and Robert Kobelja
This article describes an acylation of ferrocene that is more eco-friendly than the conventional experiment, which has been modified by replacing mineral acid with a polymeric acid catalyst and using microwave instead of conventional heating.
Birdwhistell, Kurt R.; Nguyen, Andy; Ramos, Eric J.; Kobelja, Robert. J. Chem. Educ. 2008, 85, 261.
Catalysis |
Chromatography |
Green Chemistry |
Organometallics |
Synthesis |
Transition Elements |
Brønsted-Lowry Acids / Bases
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
Synthesis of Quaternary Ammonium Salts of Tricyclic Cationic Drugs: A One-Pot Synthesis for the Bioorganic Chemistry Laboratory  Linda S. Brunauer, Abid C. Mogannam, Won B. Hwee, and James Y. Chen
Describes a one-pot conversion of tricyclic cationic drugs to their quaternary ammonium forms for a widely used bioactive drug, chlorpromazine, a phenothiazine-based antipsychotic. The conversion of parent drug to the methylated form was evaluated by qualitatively measuring its ability to induce alterations in the shape of mammalian erythrocytes.
Brunauer, Linda S.; Mogannam, Abid C.; Hwee, Won B.; Chen, James Y. J. Chem. Educ. 2007, 84, 1992.
Amines / Ammonium Compounds |
Bioorganic Chemistry |
Drugs / Pharmaceuticals |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
Isolation of Betulin and Rearrangement to Allobetulin  Brian Green, Michael D. Bentley, Bong Y. Chung, Nicholas G. Lynch, and Bruce L. Jensen
Betulin is obtained by extraction from birch bark and converted to allobetulin. Both compounds display 1H NMR spectra that include axialequatorial coupling characteristic of a C3-alcohol, conformational analysis by the use of dihedral angles and the Karplus equation, coupling patterns caused by diastereotopic protons and long-range interactions, and chemical shift values that are influenced by electronegativity and stereochemistry.
Green, Brian; Bentley, Michael D.; Chung, Bong Y.; Lynch, Nicholas G.; Jensen, Bruce L. J. Chem. Educ. 2007, 84, 1985.
Biosynthesis |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Natural Products
Using Ozone in Organic Chemistry Lab: The Ozonolysis of Eugenol  Bruce M. Branan, Joshua T. Butcher, and Lawrence R. Olsen
This organic laboratory involves the ozonolysis of eugenol (clove oil) followed by a reductive workup that generates an aldehyde easily identified by its NMR and IR spectra.
Branan, Bruce M.; Butcher, Joshua T.; Olsen, Lawrence R. J. Chem. Educ. 2007, 84, 1979.
Aldehydes / Ketones |
Gases |
IR Spectroscopy |
Laboratory Equipment / Apparatus |
Natural Products |
NMR Spectroscopy |
Synthesis |
Oxidation / Reduction
Probing the Rate-Determining Step of the Claisen–Schmidt Condensation by Competition Reactions  Kendrew K. W. Mak, Wing-Fat Chan, Ka-Ying Lung, Wai-Yee Lam, Weng-Cheong Ng, and Siu-Fung Lee
This article describes a physical organic experiment to identify the rate-determining step of the ClaisenSchmidt condensation of benzaldehyde and acetophenone by studying the linear free energy relationship.
Mak, Kendrew K. W.; Chan, Wing-Fat; Lung, Ka-Ying; Lam, Wai-Yee; Ng, Weng-Cheong; Lee, Siu-Fung. J. Chem. Educ. 2007, 84, 1819.
Aldehydes / Ketones |
Aromatic Compounds |
Gas Chromatography |
Kinetics |
Mechanisms of Reactions |
Synthesis
Synthesis of Triarylmethane and Xanthene Dyes Using Electrophilic Aromatic Substitution Reactions  James V. McCullagh and Kelly A. Daggett
In this experiment, electrophilic aromatic substitution reactions are used to synthesize several triarylmethane and xanthene dyes (fluorescein, erythrosin B, thymolphthalein, and rhodamine B) using common equipment while avoiding often troublesome, hydroscopic Lewis acids. Subsequent UVvis analysis produce spectra that match commercially available dye samples.
McCullagh, James V.; Daggett, Kelly A. J. Chem. Educ. 2007, 84, 1799.
Acids / Bases |
Aromatic Compounds |
Dyes / Pigments |
Electrophilic Substitution |
Equilibrium |
Synthesis |
UV-Vis Spectroscopy
Synthesis of Anomeric Methyl Fructofuranosides and Their Separation on an Ion-exchange Resin  Erkki Nurminen, Päivi Poijärvi, Katja Koskua, and Jari Hovinen
Treatment of d-fructose with methanol in the presence of acid as a catalyst gives a mixture of methyl--d-fructopyranoside, methyl-a-D-fructofuranoside, and methyl--d- fructofuranoside, which are separated on an ion exchange column and characterized polarimetrically.
Nurminen, Erkki; Poijärvi, Päivi; Koskua, Katja; Hovinen, Jari. J. Chem. Educ. 2007, 84, 1480.
Carbocations |
Chirality / Optical Activity |
Chromatography |
Ion Exchange |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
Carbohydrates
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
Synthesis and NMR Spectral Analysis of Amine Heterocycles: The Effect of Asymmetry on the 1H and 13C NMR Spectra of N,O-Acetals  Shahrokh Saba, James A. Ciaccio, Jennifer Espinal, and Courtney E. Aman
Describe an undergraduate organic laboratory experiment in which students prepare two N,O-acetals that differ only in a single ring substituent that introduces asymmetry, giving each compound a distinct 1H and 13C NMR spectral pattern that must be explained by students.
Saba, Shahrokh; Ciaccio, James A.; Espinal, Jennifer; Aman, Courtney E. J. Chem. Educ. 2007, 84, 1011.
Amines / Ammonium Compounds |
Chirality / Optical Activity |
Green Chemistry |
Heterocycles |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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
A Green Alternative to Aluminum Chloride Alkylation of Xylene  Grigoriy A. Sereda and Vikul B. Rajpara
Presents a simple laboratory experiment that introduces organic chemistry students to the basic principles of green technologies, such as lack of toxic or bulk byproducts, nontoxicity, and reusability of the catalyst.
Sereda, Grigoriy A.; Rajpara, Vikul B. J. Chem. Educ. 2007, 84, 692.
Alkylation |
Green Chemistry |
Catalysis |
NMR Spectroscopy |
Reactions |
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
The Aldol Addition and Condensation: The Effect of Conditions on Reaction Pathway  R. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. Barker
Describes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.
Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ. 2007, 84, 475.
Addition Reactions |
Aldehydes / Ketones |
Green Chemistry |
NMR Spectroscopy |
Reactions |
Synthesis
Plastic Solar Cells: A Multidisciplinary Field To Construct Chemical Concepts from Current Research  Rafael Gómez and José L. Segura
Presents a multidisciplinary approach to the field of organic solar cells and proposes examples of this technology to illustrate core concepts in chemistry, including the photovoltaic effect, the photoinduced electron-transfer process, the correlation between physical properties and atomic electronic structures, and molecular design.
Gómez, Rafael; Segura, José L. J. Chem. Educ. 2007, 84, 253.
Applications of Chemistry |
Molecular Properties / Structure |
Synthesis |
Materials Science
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
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
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
Chemical Aspects of General Anesthesia: Part II. Current Practices  Robert Brunsvold and Daryl L. Ostercamp
With the basic elements of balanced general anesthesia in place by the 1950s, the focus turned to developing safer and more effective agents and to improving procedures. During the last half-century a new generation of intravenous induction anesthetics, inhalational anesthetics, and muscle relaxants has emerged.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1826.
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
Chemical Aspects of General Anesthesia: Part I. From Ether to Halothane  Robert Brunsvold and Daryl L. Ostercamp
Summarizes general anesthesia from 1846 to 1956. Events leading up to the adoption of a "balanced" approach, where a sequence of individual compounds is used rather than a single agent, are described.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1821.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis
Chemical Aspects of Local and Regional Anesthesia  Robert Brunsvold and Daryl L. Ostercamp
The chemistry that underlies the development of local and regional anesthesia is explored. Emphasis is placed upon the importance of acidity constants and lipophilic versus hydrophilic character in interpreting what affect a particular compound has upon biological processes.
Brunsvold, Robert; Ostercamp, Daryl L. J. Chem. Educ. 2006, 83, 1816.
Acids / Bases |
Bioorganic Chemistry |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Synthesis |
Applications of Chemistry
Projects That Assist with Content in a Traditional Organic Chemistry Course  John J. Esteb, John R. Magers, LuAnne McNulty, and Anne M. Wilson
Describes two projects in organic chemistry, the reaction notebook and the end-of-semester synthesis activity, that are designed to stimulate student ownership of and engagement with course content.
Esteb, John J.; Magers, John R.; McNulty, LuAnne; Wilson, Anne M. J. Chem. Educ. 2006, 83, 1807.
Enrichment / Review Materials |
Mechanisms of Reactions |
Reactions |
Synthesis |
Student-Centered Learning
Synthesis of meso-Diethyl-2,2′-dipyrromethane in Water. An Experiment in Green Organic Chemistry  Abilio J. F. N. Sobral
In this laboratory activity, students are introduced to the synthesis of dipyrromethanes important precursors for porphyrin and calix[4]pyrrolethrough the acid-catalyzed condensation of pyrrole and 3-pentanone to produce meso-diethyl-2,2'-dipyrromethane.
Sobral, Abilio J. F. N. J. Chem. Educ. 2006, 83, 1665.
Aldehydes / Ketones |
Aqueous Solution Chemistry |
Green Chemistry |
Synthesis
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
3,5-Diarylisoxazoles: Individualized Three-Step Synthesis and Isomer Determination Using 13C NMR or Mass Spectroscopy  Chad E. Stephens and Reem K. Arafa
Describes the three-step synthesis and definitive characterization of a 3,5-diarylisoxazole via the chalcone and chalcone dibromide. The project is individualized with regard to compound purification, characterization, and literature searches as each student prepares a differently substituted chalcone.
Stephens, Chad E.; Arafa, Reem K. J. Chem. Educ. 2006, 83, 1336.
Alkenes |
Heterocycles |
IR Spectroscopy |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
Spectroscopy
Calix[4]pyrrole: Synthesis and Anion-Binding Properties. An Organic Chemistry Laboratory Experiment  James A. Shriver and Scott G. Westphal
Simple calixpyrrole macrocycles provide an easy-to-synthesize example of an anion-binding agent that can be included in the undergraduate laboratory curriculum. The inclusion of a test for anion binding also makes this procedure suitable for a more advanced audience and supplies a bridge for the introduction of supramolecular chemistry and a typical hostguest interaction.
Shriver, James A.; Westphal, Scott G. J. Chem. Educ. 2006, 83, 1330.
Aromatic Compounds |
Hydrogen Bonding |
Molecular Recognition |
Synthesis |
Thin Layer Chromatography
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
Synthesis and Analysis of a Versatile Imine for the Undergraduate Organic Chemistry Laboratory  Jacqueline Bennett, Kristen Meldi, and Christopher Kimmell II
In this experiment students prepare and analyze N-p-methoxyphenyl (N-PMP) alpha-imino ethyl glyoxalate, an imine that has been used in the synthesis of biologically active molecules. The stability and versatility of this imine allow it to be used in subsequent reactions, offering a variety of possible multistep synthetic strategies.
Bennett, Jacqueline; Meldi, Kristen; Kimmell, Christopher, II. J. Chem. Educ. 2006, 83, 1221.
Aldehydes / Ketones |
Gas Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis
Purification and Modification of Fullerene C60 in the Undergraduate Laboratory  Tracey Spencer, Barney Yoo, and Kent Kirshenbaum
Describes an experiment for the extraction and column purification of buckminsterfullerene from fullerene-rich soot followed by a one-pot 1,3-dipolar cycloaddition of an azomethine ylide. Characterization of the starting material and product can be performed by UVVis, MS, 1H NMR, and 13C NMR.
Spencer, Tracey; Yoo, Barney; Kirshenbaum, Kent. J. Chem. Educ. 2006, 83, 1218.
Aromatic Compounds |
Chromatography |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Synthesis |
Nanotechnology |
Reactions
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
Stereospecific Synthesis of the Geometrical Isomers of a Natural Product  T. Grove, D. DiLella, and E. Volker
Presents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.
Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ. 2006, 83, 1055.
Alkenes |
Computational Chemistry |
Gas Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Stereochemistry |
Synthesis
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
Synthesis and Cytotoxic Properties of Chalcones: An Interactive and Investigative Undergraduate Laboratory Project at the Interface of Chemistry and Biology  John Dickson, Lloyd Flores, Michelle Stewart, Regan LeBlanc, Hari N. Pati, Moses Lee, and Herman Holt
This project combines the synthesis of a small library of 30 appropriately substituted chalcones, the measurement of their cytotoxic properties, and the study of their structureactivity relationships using computational chemistry.
Dickson, John; Flores, Lloyd; Stewart, Michelle; LeBlanc, Regan; Pati, Hari N.; Lee, Moses; Holt, Herman. J. Chem. Educ. 2006, 83, 934.
Biotechnology |
Combinatorial Chemistry |
Conformational Analysis |
Medicinal Chemistry |
Molecular Modeling |
Natural Products |
Synthesis
A Sequence of Linked Experiments, Suitable for Practical Courses of Inorganic, Organic, Computational Chemistry, and NMR Spectroscopy  Grigoriy A. Sereda
A sequence of investigations associated with the iodochlorination of styrene and 1-hexene is described. The sequence is flexible enough to be used in inorganic, organic, computational, and instrumental courses.
Sereda, Grigoriy A. J. Chem. Educ. 2006, 83, 931.
Alkenes |
Computational Chemistry |
Constitutional Isomers |
MO Theory |
NMR Spectroscopy |
Synthesis
A Simple Combinatorial Experiment Based on Fischer Esterification. An Experiment Suitable for the First-Semester Organic Chemistry Lab  Peter A. Wade, Susan A. Rutkowsky, and Daniel B. King
Describes a combinatorial experiment for the synthesis of esters by Fischer esterification in which a total of eight esters are prepared as six mixtures.
Wade, Peter A.; Rutkowsky, Susan A.; King, Daniel B. J. Chem. Educ. 2006, 83, 927.
Alcohols |
Carboxylic Acids |
Combinatorial Chemistry |
Equilibrium |
Esters |
Gas Chromatography |
Synthesis
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
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 Unsymmetrical Alkynes via the Alkylation of Sodium Acetylides. An Introduction to Synthetic Design for Organic Chemistry Students  Jennifer N. Shepherd and Jason R. Stenzel
Teams of students design a microscale synthesis of an unsymmetrical alkyne using commercially available terminal alkynes and alkyl halides and characterize the resulting products using TLC, IR, and 1H NMR spectroscopy. Depending on the chosen reactants, students observe both substitution and elimination products, or in some cases, no reaction at all.
Shepherd, Jennifer N.; Stenzel, Jason R. J. Chem. Educ. 2006, 83, 425.
Alkylation |
Alkynes |
Elimination Reactions |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Nucleophilic Substitution |
Synthesis
4-Dimethylaminopyridine or Acid-Catalyzed Syntheses of Esters: A Comparison  Annemieke W. C. van den Berg and Ulf Hanefeld
Students compare acid-catalyzed ester synthesis and the 4-dimethylaminopyridine-catalyzed reaction. Based on the outcome of the experiments, students discuss the different reaction mechanisms and reason why different products are formed.
van den Berg, Annemieke W. C.; Hanefeld, Ulf. J. Chem. Educ. 2006, 83, 292.
Acids / Bases |
Catalysis |
Chromatography |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Synthesis |
Mechanisms of Reactions
Convenient Microscale Synthesis of a Coumarin Laser Dye Analog  Evangelos Aktoudianakis and Andrew P. Dicks
Describes the Knoevenagel synthesis of 3-acetyl-7-(diethylamino)-2H-1-benzopyran-2-one, a fluorescent coumarin laser dye analog.
Aktoudianakis, Evangelos; Dicks, Andrew P. J. Chem. Educ. 2006, 83, 287.
Aromatic Compounds |
Fluorescence Spectroscopy |
IR Spectroscopy |
Microscale Lab |
Synthesis |
NMR Spectroscopy |
UV-Vis Spectroscopy
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
Microwave-Assisted Synthesis of a Natural Insecticide on Basic Montmorillonite K10 Clay. Green Chemistry in the Undergraduate Organic Laboratory  Matthew R. Dintzner, Paul R. Wucka, and Thomas W. Lyons
Describes a microwave-assisted, solvent-free, one-pot synthesis of a naturally occurring insecticide catalyzed by naturally benign, base-washed Montmorillonite K10 clay. The reaction features several interesting mechanistic considerations, including an electrophilic aromatic addition, dehydration, and intramolecular hetero-DielsAlder cyclization.
Dintzner, Matthew R.; Wucka, Paul R.; Lyons, Thomas W. J. Chem. Educ. 2006, 83, 270.
Chromatography |
Green Chemistry |
Mass Spectrometry |
NMR Spectroscopy |
Synthesis |
IR Spectroscopy |
Spectroscopy
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
Derivatization of Fullerenes: An Organic Chemistry Laboratory  Charles T. Cox Jr. and Melanie M. Cooper
Presents two undergraduate organic chemistry laboratories detailing the synthesis of fullerene derivatives, using the Bingel (carbene insertion) and Prato (1,3-dipolar addition) protocols.
Cox, Charles T., Jr.; Cooper, Melanie M. J. Chem. Educ. 2006, 83, 99.
Acids / Bases |
Addition Reactions |
Chromatography |
Heterocycles |
IR Spectroscopy |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
UV-Vis Spectroscopy
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
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
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
Polypyrazolylborates: Scorpionates  Swiatoslaw Trofimenko
Key features of polypyrazolylborates (also known as scorpionates because of certain specific features of their coordination chemistry) and examples of their use in modeling biologically active compounds are briefly presented.
Trofimenko, Swiatoslaw. J. Chem. Educ. 2005, 82, 1715.
Coordination Compounds |
Heterocycles |
Synthesis |
Bioinorganic Chemistry |
Molecular Properties / Structure
A GC–MS Analysis of an SN2 Reaction for the Organic Laboratory  Malgorzata M. Clennan and Edward L. Clennan
This experiment utilizes an SN2 reaction between an alkyl bromide and potassium acetate to introduce the use of mass spectrometry for structural identification. It also provides students with experience in organic synthesis, the use of IR to identify functional groups, and the use of gas chromatography and response factors to determine product ratios.
Clennan, Malgorzata M.; Clennan, Edward L. J. Chem. Educ. 2005, 82, 1676.
IR Spectroscopy |
Mass Spectrometry |
Synthesis |
Chromatography |
Esters |
Mechanisms of Reactions |
Microscale Lab |
Gas Chromatography
Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide  Marsha R. Baar and Kristin Wustholz
endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride.
Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ. 2005, 82, 1393.
Asymmetric Synthesis |
Microscale Lab |
Stereochemistry |
Addition Reactions |
Alkenes |
IR Spectroscopy |
NMR Spectroscopy
A Green Polymerization of Aspartic Acid for the Undergraduate Organic Laboratory  George D. Bennett
Based on a technology that won a Presidential Green Chemistry Challenge Award, this experiment involves the thermal polymerization of aspartic acid and subsequent hydrolysis to give sodium poly(aspartate). The procedure is suitable for introducing students to the important topic of polymers and for illustrating several of the principles of green chemistry.
Bennett, George D. J. Chem. Educ. 2005, 82, 1380.
Green Chemistry |
Synthesis |
Industrial Chemistry |
Natural Products |
Polymerization |
Proteins / Peptides
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
Generation, Isolation, and Characterization of a Stable Enol from Grignard Addition to a Bis-Ester. A Microscale Experiment for the Undergraduate Organic Chemistry Laboratory  Olivier J.-C. Nicaise, Kyle F. Ostrom, and Brent J. Dalke
A microscale experiment for the undergraduate organic chemistry laboratory that consists of preparing and characterizing an alpha-ketoester and its corresponding, remarkably stable enol form, has been developed. The reaction is that of a Grignard reagent with a bis-ester. A difference in reaction temperature is responsible for the selective generation of the alpha-ketoester and the enol ester. Analysis of spectral data (1H NMR and IR) and a knowledge of organic reactions allows the students to determine the detailed structure of the two reaction products and also to suggest a mechanism for their formation. This experiment introduces students to the concept of stability of the tetrahedral intermediate in acyl-transfer reactions. It also gives them a taste of the unexpected.
Nicaise, Olivier J.-C.; Ostrom, Kyle F.; Dalke, Brent J. J. Chem. Educ. 2005, 82, 1059.
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Organometallics |
Reactive Intermediates |
Synthesis
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
Formation of α-Tetralone by Intramolecular Friedel–Crafts Acylation  Michael S. Holden, R. David Crouch, and Kathryn A. Barker
A microscale procedure is described for the formation of the industrially-important compound alpha-tetralone. This is an example of an intramolecular FriedelCrafts acylation, utilizing 4-phenylbutanoic acid and a proton source. The title reaction demonstrates the concept of ring-forming reactions and highlights the use of carboxylic acids as an electrophile precursor in electrophilic aromatic substitution reactions.
Holden, Michael S.; Crouch, R. David; Barker, Kathryn A. J. Chem. Educ. 2005, 82, 934.
Aromatic Compounds |
Microscale Lab |
Synthesis |
Carboxylic Acids |
IR Spectroscopy |
NMR Spectroscopy
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
The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of Stilbene  Lallie C. McKenzie, Lauren M. Huffman, and James E. Hutchison
We describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.
McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ. 2005, 82, 306.
Synthesis |
Green Chemistry |
Aromatic Compounds |
Addition Reactions |
Alkenes
The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors Laboratory  Christopher J. Nichols and Melissa R. Taylor
A six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column.
Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ. 2005, 82, 105.
Chirality / Optical Activity |
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Alkenes |
Addition Reactions
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
A Discovery-Based Friedel–Crafts Acylation Experiment: Student-Designed Experimental Procedure  Anne McElwee Reeve
A discovery-based FriedelCrafts acylation experiment that includes a student-designed procedure, spectroscopic analysis of an unknown aromatic product, and molecular modeling is described. Students design the synthetic procedure and workup for the acylation of an unknown aromatic starting material in an instructor-guided classroom discussion that integrates concepts from the first semester of organic lab into a new context.
Reeve, Anne McElwee. J. Chem. Educ. 2004, 81, 1497.
Aromatic Compounds |
Chromatography |
IR Spectroscopy |
Molecular Modeling |
NMR Spectroscopy |
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
Solvent-Free Wittig Reaction: A Green Organic Chemistry Laboratory Experiment  Sam H. Leung and Stephen A. Angel
In this experiment (E)- and (Z)-1-(4-bromophenyl)-2-phenylethene are synthesized by a solvent-free Wittig reaction. The reaction is effected by grinding the reactants in a mortar with a pestle. Both the E and Z isomers of the product are produced as evidenced by thin-layer chromatography and 1H NMR analysis. The E isomer is isolated by crystallization with ethanol in this experiment. In addition to learning about the Wittig reaction, students are also introduced to the ideas of mechanochemistry and green chemistry.
Leung, Sam H.; Angel, Stephen A. J. Chem. Educ. 2004, 81, 1492.
Chromatography |
Green Chemistry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Reactions |
Aldehydes / Ketones |
Alkenes
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
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
Solvent-Free Synthesis of Chalcones  Daniel R. Palleros
The solvent-free synthesis of 20 chalcones was carried out by grinding the benzaldehyde (unsubstituted, 4-methyl, 4-methoxy, 3-chloro, or 4-chloro) and the acetophenone (unsubstituted, 4-methyl, 4-bromo, or 4-methoxy) in the presence of solid sodium hydroxide with a mortar and pestle. In general, the chalcones were obtained in high yields and high purity. Minor quantities of ketol and Michael addition product were detected by NMR spectroscopy. These side-products were easily removed by recrystallization.
Palleros, Daniel R. J. Chem. Educ. 2004, 81, 1345.
Green Chemistry |
NMR Spectroscopy |
Synthesis |
Solids |
Laboratory Management
Preparation and Investigation of Monodentate and Bridging Pyrazole Complexes  Wynne Evans
This practical exercise describes the preparation and characterization of h1-coordinated pyrazole and 3,5-dimethylpyrazole nickel species and the investigation of their reactions with triethylamine. The latter reaction provides a route to preparing a polymer with bridging pyrazolato ligands, coordinating in an exobidentate (N, N?) fashion. We use this experiment, with undergraduate chemistry students, as part of a course providing an introduction to coordination chemistry. The exercise could be extended to take the form of an individual or class project. Suggestions for variations on the described experiment are included.
Evans, Wynne. J. Chem. Educ. 2004, 81, 1191.
Coordination Compounds |
Synthesis |
IR Spectroscopy |
Magnetic Properties |
Organometallics |
Titration / Volumetric Analysis |
Transition Elements |
UV-Vis Spectroscopy |
Spectroscopy |
Crystal Field / Ligand Field Theory
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
Syntheses and Characterization of Ruthenium(II) Tetrakis(Pyridine) Complexes. An Advanced Coordination Chemistry Experiment or Mini-Project  Benjamin J. Coe
This experiment involves the syntheses of several coordination complexes of ruthenium(II) and their characterization by using various spectroscopic and spectrometric techniques.
Coe, Benjamin J. J. Chem. Educ. 2004, 81, 718.
Coordination Compounds |
IR Spectroscopy |
Synthesis |
Mass Spectrometry |
NMR Spectroscopy |
UV-Vis Spectroscopy
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 Darzens Condensation: Structure Determination through Spectral Analysis and Understanding Substrate Reactivity  R. David Crouch, Michael S. Holden, and Candice A. Romany
The Darzens condensation involves two steps that are typically included in the sophomore organic curriculum: an aldol reaction followed by an intramolecular nucleophilic substitution.
Crouch, R. David; Holden, Michael S.; Romany, Candice A. J. Chem. Educ. 2004, 81, 711.
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Mechanisms of Reactions |
Aldehydes / Ketones
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
Developing Investigation Skills in an Introductory Multistep Synthesis Using Fluorene Oxidation and Reduction  Mark G. Stocksdale, Steven E. S. Fletcher, Ian Henry, Paul J. Ogren, Michael A. G. Berg, Roy D. Pointer, and Barrett W. Benson
A two-step reaction sequence in the beginning organic laboratory provides a useful introduction to the importance of multistep synthesis. In addition to introducing several common synthetic methods and techniques, a two-step preparation can quickly establish the importance of testing alternative reactions in order to optimize intermediate yields.
Stocksdale, Mark G.; Fletcher, Steven E. S.; Henry, Ian; Ogren, Paul J.; Berg, Michael A. G.; Pointer, Roy D.; Benson, Barrett W. J. Chem. Educ. 2004, 81, 388.
Chromatography |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds |
Oxidation / Reduction
The Monosodium Glutamate Story: The Commercial Production of MSG and Other Amino Acids  Addison Ault
Examples of the industrial synthesis of pure amino acids are presented. The emphasis is on the synthesis of (S)-glutamic acid and, to a lesser extent, (S)-lysine and (R,S)-methionine. These amino acids account for about 90% of the total world production of amino acids.
Ault, Addison. J. Chem. Educ. 2004, 81, 347.
Amino Acids |
Biotechnology |
Chirality / Optical Activity |
Consumer Chemistry |
Enzymes |
Natural Products |
Stereochemistry |
Synthesis |
Food Science
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
Microscale Synthesis and Spectroscopic Analysis of Flutamide, an Antiandrogen Prostate Cancer Drug  Ryan G. Stabile and Andrew P. Dicks
The synthesis involves N-acylation of a trisubstituted aromatic compound, 3-trifluoromethyl-4-nitroaniline. The procedure is easily adapted to generate structural analogues of flutamide. A significant feature is the curricular flexibility afforded by this experiment.
Stabile, Ryan G.; Dicks, Andrew P. J. Chem. Educ. 2003, 80, 1439.
Drugs / Pharmaceuticals |
IR Spectroscopy |
Mechanisms of Reactions |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Aromatic Compounds
A Series of Small-Scale, Discovery-Based Organic Laboratory Experiments Illustrating the Concepts of Addition, Substitution, and Rearrangement  Judith S. Moroz, Janice L. Pellino, and Kurt W. Field
Multistep, microscale organic laboratory experiments are presented that illustrate addition, substitution, and rearrangement reactions.
Moroz, Judith S.; Pellino, Janice L.; Field, Kurt W. J. Chem. Educ. 2003, 80, 1319.
IR Spectroscopy |
Mass Spectrometry |
Microscale Lab |
NMR Spectroscopy |
Synthesis |
Addition Reactions |
Mechanisms of Reactions
The Study of Elimination Reactions Using Gas Chromatography: An Experiment for the Undergraduate Organic Laboratory  Devin Latimer
This article describes an investigation of elimination reactions of alkyl halides. 1-Bromopentane or 2-bromopentane are reacted with either sodium ethoxide or potassium tert-butoxide. Gas chromatography is used to monitor the relative amounts of 1-pentene, (E)-2-pentene, and (Z)-2-pentene produced.
Latimer, Devin. J. Chem. Educ. 2003, 80, 1183.
Chromatography |
Instrumental Methods |
Synthesis |
Gas Chromatography |
Elimination Reactions |
Mechanisms of Reactions |
Alkenes |
Stereochemistry
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
"Chiral Acetate": The Preparation, Analysis, and Applications of Chiral Acetic Acid  Addison Ault
Production of chiral acetic acid using deuterium and tritium and its application to understanding stereochemistry and the specificity of enzymatic reactions.
Ault, Addison. J. Chem. Educ. 2003, 80, 333.
Chirality / Optical Activity |
Enzymes |
Isotopes |
Synthesis |
Stereochemistry |
Enrichment / Review Materials |
Carboxylic Acids |
Enantiomers |
Reactions |
Mechanisms of Reactions
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
Dendrimers: Branching Out of Polymer Chemistry  Eric E. Simanek and Sergio O. Gonzalez
Addresses synthetic concepts surrounding dendrimers including the use of protecting groups, functional group interconversions, and convergent and divergent synthetic strategies.
Simanek, Eric E.; Gonzalez, Sergio O. J. Chem. Educ. 2002, 79, 1222.
Materials Science |
Synthesis |
Molecular Properties / Structure |
Addition Reactions |
Aromatic Compounds |
Alkylation |
Nucleophilic Substitution
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
Applications of the Sol–Gel Process Using Well-Tested Recipes  A. Celzard and J. F. Marêché
Several simple procedures for making sol-gels and exploring their applications.
Celzard, A.; Marêché, J. F. J. Chem. Educ. 2002, 79, 854.
Materials Science |
Synthesis |
Solids |
Solid State Chemistry |
Applications of Chemistry
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
Synthesis and Characterization of a Gasoline Oxygenate, Ethyl tert-Butyl Ether  Craig J. Donahue, Teresa D'Amico, and Jennifer A. Exline
Procedure for the synthesis and characterization of ethyl tert-butyl ether.
Donahue, Craig J.; D'Amico, Teresa; Exline, Jennifer A. J. Chem. Educ. 2002, 79, 724.
Chromatography |
Synthesis |
Ethers |
Gas Chromatography |
IR Spectroscopy |
Qualitative Analysis
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
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
Diastereoselective Synthesis of a Strawberry Flavoring Agent by Epoxidation of Ethyl trans-b-Methylcinnamate  Gayle J. Pageau, Rodwell Mabaera, Kathryn M. Kosuda, Tamara A. Sebelius, Ali H. Ghaffari, Kenneth A. Kearns, Jean P. McIntyre, Tina M. Beachy, and Dasan M. Thamattoor
Synthesis of the "strawberry aldehyde" epoxide, a well-known food and perfume additive.
Pageau, Gayle J.; Mabaera, Rodwell; Kosuda, Kathryn M.; Sebelius, Tamara A.; Ghaffari, Ali H.; Kearns, Kenneth A.; McIntyre, Jean P.; Beachy, Tina M.; Thamattoor, Dasan M. J. Chem. Educ. 2002, 79, 96.
Molecular Modeling |
NMR Spectroscopy |
Synthesis |
Stereochemistry |
Epoxides |
Consumer Chemistry |
Food Science
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
Synthesis and Analysis of a Solvatochromic Dye, 1-(p-Dimethylaminophenyl)-2-nitroethylene. An Advanced Undergraduate Laboratory Experiment  Dana L. Richter-Egger, Aaron Tesfai, Spencer J. Flamm, and Sheryl A. Tucker
Synthesis and analysis of 1-(p-dimethylaminophenyl)-2-nitroethylene.
Richter-Egger, Dana L.; Tesfai, Aaron; Flamm, Spencer J.; Tucker, Sheryl A. J. Chem. Educ. 2001, 78, 1375.
Fluorescence Spectroscopy |
Synthesis |
Undergraduate Research |
UV-Vis Spectroscopy |
Dyes / Pigments |
Amines / Ammonium Compounds |
Aromatic Compounds |
Alkenes
Synthesis and Use of Jacobsen's Catalyst: Enantioselective Epoxidation in the Introductory Organic Laboratory  John Hanson
Laboratory series to introduce students to an important synthetic method and many common techniques used in running reactions, purifying products, and characterizing compounds.
Hanson, John. J. Chem. Educ. 2001, 78, 1266.
Catalysis |
Chirality / Optical Activity |
Synthesis |
Organometallics |
Stereochemistry |
Epoxides |
Enantiomers |
Aromatic Compounds
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
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
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
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
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 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
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
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
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
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
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
Reaction of Dibenzoylethylene with Hydriodic Acid  Fred H. Greenberg
Dibenzoylethylene is treated with hydriodic acid in acetone at room temperature to obtain dibenzoylethane rather than the expected dibenzoyliodoethane. Students identify the product by the use of NMR and IR spectra and are given a nonpictorial representation of a mechanism and asked to supply the structures of the relevant intermediates.
Greenberg, Fred H. J. Chem. Educ. 2000, 77, 505.
Microscale Lab |
Synthesis |
NMR Spectroscopy |
IR Spectroscopy |
Mechanisms of Reactions |
Reactive Intermediates
Multicomponent Reactions: A Convenient Undergraduate Organic Chemistry Experiment  Ricardo Bossio, Stefano Marcaccini, Carlos F. Marcos, and Roberto Pepino
Two experiments for the synthesis of a -lactam and a succinimide, based on a 4-component Ugi condensation. The experimental procedures for both syntheses are identical except for the choice of the starting amine, whose electron richness is controlled by the presence or absence of an electron-withdrawing group.
Bossio, Ricardo; Marcaccini, Stefano; Marcos, Carlos F.; Pepino, Roberto. J. Chem. Educ. 2000, 77, 382.
Synthesis |
Drugs / Pharmaceuticals |
IR Spectroscopy |
NMR Spectroscopy |
Mechanisms of Reactions |
Molecular Properties / Structure
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
Microwave Irradiation Reactions: Synthesis of Analgesic Drugs  Gholam A. Mirafzal and Jolene M Summer
Over-the-counter analgesics such as aspirin, acetanilide, phenacetin, and acetaminophen are conveniently prepared in a microwave at 30% power for five minutes. Recrystallization from appropriate solvents results in solid products in good to excellent yields.
Mirafzal, Gholam A.; Summer, Jolene M. J. Chem. Educ. 2000, 77, 356.
Drugs / Pharmaceuticals |
Synthesis |
Medicinal Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds |
Esters
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
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
Introducing Chiroscience into the Organic Laboratory Curriculum  Kenny B. Lipkowitz, Tim Naylor, and Keith S. Anliker
"Chiroscience" is a young but robust industry linking science and technology with chemistry and biology; includes description of an asymmetric reduction of a ketone followed by an assessment of the enantiomeric excess by GC using a chiral stationary phase.
Lipkowitz, Kenny B.; Naylor, Tim; Anliker, Keith S. J. Chem. Educ. 2000, 77, 305.
Chirality / Optical Activity |
Chromatography |
Mechanisms of Reactions |
Synthesis |
Separation Science |
Stereochemistry |
Gas Chromatography |
Aldehydes / Ketones
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 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
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
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
"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
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
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
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 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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 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
The Baylis-Hillman Reaction: Synthesizing a Compound and Explaining Its Formation  Crouch, R. David; Nelson, Todd D.
Experimental procedure for the synthesis of an unpredictable and unknown mechanism to be identified and described by students through analytical techniques (spectroscopy).
Crouch, R. David; Nelson, Todd D. J. Chem. Educ. 1995, 72, A6.
Synthesis |
Mechanisms of Reactions |
NMR Spectroscopy |
IR Spectroscopy |
UV-Vis Spectroscopy |
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
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
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
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
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
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
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
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
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
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
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
Microwave Synthesis of Tetraphenylcyclopentadienone and Dimethyl Tetraphenylphthalate  Elder, John W.
Procedure for using a microwave to synthesize tetraphenylcyclopentadienone and dimethyl tetraphenylphthalate.
Elder, John W. J. Chem. Educ. 1994, 71, A142.
Microscale Lab |
Laboratory Equipment / Apparatus |
Synthesis |
Aromatic Compounds |
Esters |
Amines / Ammonium Compounds
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
A More Affordable Undergraduate Experiment on the Reduction of Acetophenone by Yeast  Lee, Moses; Huntington, Martha
Preparation of Mosher's esters through the reduction of acetophenone with baker's yeast.
Lee, Moses; Huntington, Martha J. Chem. Educ. 1994, 71, A62.
Microscale Lab |
Aromatic Compounds |
Aldehydes / Ketones |
Oxidation / Reduction |
Stereochemistry |
Chirality / Optical Activity |
Esters |
Synthesis
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
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
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
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
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
The microscale synthesis and the structure determination of endo-9-methoxycarbonyl-3-oxatricyclo[4,2,1,0 4,5]-2-nonanone.  Lee, Moses.
The microscale synthesis and the structure determination of endo-9-methoxycarbonyl-3-oxatricyclo[4,2,1,0 4,5]-2-nonanone.
Lee, Moses. J. Chem. Educ. 1992, 69, A172.
Microscale Lab |
Synthesis |
Aldehydes / Ketones |
Fourier Transform Techniques |
NMR Spectroscopy |
IR Spectroscopy |
Gas Chromatography |
Thin Layer Chromatography |
Instrumental Methods
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
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
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
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
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
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
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
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
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
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
Synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct: An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry  Harrison, Ernest A., Jr.
An organic chemistry experiment utilizing NMR spectroscopy to assign endo stereochemistry via synthesis of a bicyclo[2.2.1]heptene Diels-Alder adduct.
Harrison, Ernest A., Jr. J. Chem. Educ. 1991, 68, 426.
Alkanes / Cycloalkanes |
Synthesis |
Alkenes |
Aromatic Compounds |
NMR Spectroscopy |
Thin Layer Chromatography
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
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
A One-Step Synthesis of Cinnamic Acids Using Malonic Acid: The Verley-Doebner Modification of the Knoevenagel Condensation  Kolb, Kenneth E.; Field, Kurt W.; Schatz, Paul F.
With this procedure malonic acid itself, rather than its diester, can be effectively condensed with benzaldehyde to produce trans-cinnamic acid.
Kolb, Kenneth E.; Field, Kurt W.; Schatz, Paul F. J. Chem. Educ. 1990, 67, A304.
Microscale Lab |
Synthesis |
Acids / Bases |
Aromatic Compounds |
Aldehydes / Ketones |
Carboxylic Acids
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
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
Synthesis of 5-nitrofurfural diacetate and 5-nitrofurfural semicarbazone: An undergraduate laboratory experiment  Li, Xiaorong; Liu, Qianguang; Chang, James C.
Demonstrates how to nitrate an aromatic compound having an aldehyde group that can be oxidized by nitrating agents.
Li, Xiaorong; Liu, Qianguang; Chang, James C. J. Chem. Educ. 1990, 67, 986.
Synthesis |
Aldehydes / Ketones |
Esters |
Ethers |
Electrophilic Substitution |
Aromatic Compounds |
NMR Spectroscopy
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
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
Magnetic and spectral properties of an airstable d1 titanium complex  Pickering, Miles
Synthesis and analysis of a Ti(III)-urea complex.
Pickering, Miles J. Chem. Educ. 1985, 62, 442.
Magnetic Properties |
Transition Elements |
Metals |
Synthesis |
Crystal Field / Ligand Field Theory |
IR Spectroscopy
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
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
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
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
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
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 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 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
A reinvestigation of the synthesis of 4-methyl-3-heptanol  Hoffman, Robert V.; Alexander, M. D.; Buntain, Gregory; Hardenstein, Richard; Mattox, Cynthia; McLaughlin, Susan; McMinn, Denise; Spray, Scott; White, Steven
A previously reported laboratory may have reported gas chromatographic separation of the 4-methyl-3-heptanol diastereomiers in error. The side reactions in the Grignard reaction account for the observed results.
Hoffman, Robert V.; Alexander, M. D.; Buntain, Gregory; Hardenstein, Richard; Mattox, Cynthia; McLaughlin, Susan; McMinn, Denise; Spray, Scott; White, Steven J. Chem. Educ. 1983, 60, 78.
Hormones |
Alcohols |
Grignard Reagents |
IR Spectroscopy |
NMR Spectroscopy |
Aldehydes / Ketones |
Gas Chromatography |
Synthesis |
Natural Products
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
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
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
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 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
Sulcatol: Synthesis of an aggregation pheromone  Black, Shirley-Ann; Slessor, Keith N.
Synthesis of the aggregation pheromone of the ambrosia beetle, an insect pest of harvested timber in the Pacific North Coast.
Black, Shirley-Ann; Slessor, Keith N. J. Chem. Educ. 1982, 59, 255.
Synthesis |
Natural Products |
Molecular Properties / Structure |
Chirality / Optical Activity |
NMR Spectroscopy |
IR Spectroscopy |
Applications of Chemistry
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
An undergraduate laboratory program project involving photocyclizations in independent syntheses of novel chrysenes and phenanthrenes  Letcher, R. M.
This experiment attempts to fulfill such objectives as providing meaningful and viable preparative reactions, providing an opportunity for independent laboratory work within a project framework and under conditions of nearly equal opportunity and experience.
Letcher, R. M. J. Chem. Educ. 1981, 58, 1020.
Undergraduate Research |
Synthesis |
Aromatic Compounds |
Photochemistry |
Diastereomers |
NMR Spectroscopy |
Alcohols |
Thin Layer Chromatography
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
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
Conversion of (+)-Limonene to (-)-Carvone: An organic laboratory sequence of local interest  Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B.
Orange oil is converted to one of the components of spearmint oil; the detectable odor difference is due to stereochemical factors.
Rothenberger, Otis S.; Krasnoff, Stuart B.; Rollins, Ronald B. J. Chem. Educ. 1980, 57, 741.
Stereochemistry |
Molecular Properties / Structure |
Synthesis |
Separation Science |
Industrial Chemistry |
Applications of Chemistry |
Enantiomers
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
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
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
Drugs in the chemistry laboratory: The conversion of acetaminophen into phenacetin  Volker, Eugene J.; Pride, Ernest; Hough, Charles
The phenolic alcohol group of acetaminophen is alkylated with ethyl iodide using the basic catalyst K2CO3.
Volker, Eugene J.; Pride, Ernest; Hough, Charles J. Chem. Educ. 1979, 56, 831.
Nonmajor Courses |
Applications of Chemistry |
Medicinal Chemistry |
Drugs / Pharmaceuticals |
Synthesis |
Catalysis |
Phenols |
Alcohols
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
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
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
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
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
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
"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
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
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
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
Phase transfer catalysis. Part II: Synthetic applications  Gokel, George W.; Weber, William P.
In this month's continuation of an article, the authors have catalogued a number of illustrative examples so that the range of applicability of phase transfer catalysis will be.
Gokel, George W.; Weber, William P. J. Chem. Educ. 1978, 55, 429.
Phases / Phase Transitions / Diagrams |
Catalysis |
Aromatic Compounds |
Organometallics |
Nucleophilic Substitution |
Synthesis |
Esters |
Oxidation / Reduction |
Alkylation
Project for problem-oriented undergraduate organic or integrated undergraduate laboratory  Silveira, Augustine, Jr.
This paper reports on an open-ended project which allows a great degree of flexibility in the laboratory. The project provided about a 6-week study for groups of 24 students each.
Silveira, Augustine, Jr. J. Chem. Educ. 1978, 55, 57.
Synthesis |
Undergraduate Research |
Spectroscopy |
Diastereomers |
Addition Reactions |
MO Theory |
Elimination Reactions |
Thermodynamics |
Kinetics
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
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
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
Synthesis of 4-methyl-3-heptanol and 4-methyl-3-heptanone. Two easily synthesized insect pheromones  Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S.
A two step reaction sequence involving the Grignard synthesis of an alcohol followed by oxidation of this alcohol to the corresponding ketone.
Einterz, Robert M.; Ponder, Jay W.; Lenox, Ronald S. J. Chem. Educ. 1977, 54, 382.
Natural Products |
Synthesis |
Applications of Chemistry |
Grignard Reagents |
Mechanisms of Reactions |
Stereochemistry |
Alcohols |
Aldehydes / Ketones
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
Syntheses and rearrangements of cage molecules related to cubane  Jefford, Charles W.
This article looks at the synthesis of cubane, basketene, miscellaneous homocubane chemistry, snoutene, triqunacene, hypostrophene, tris-homocubane, and catalysis by transition metals.
Jefford, Charles W. J. Chem. Educ. 1976, 53, 477.
Catalysis |
Transition Elements |
Alkenes |
Synthesis |
Aromatic Compounds |
Heterocycles |
Alcohols
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
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 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
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
An integrated synthesis laboratory for the sophomore year  Pearson, Wesley A.; Finholt, Albert E.
Outlines the compounds synthesized and the techniques used in a two-semester integrated laboratory sequence for sophomores.
Pearson, Wesley A.; Finholt, Albert E. J. Chem. Educ. 1975, 52, 236.
Synthesis |
Coordination Compounds |
IR Spectroscopy |
NMR Spectroscopy |
UV-Vis Spectroscopy |
Chromatography
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Preparation of p-anisole: An organic chemistry experiment  Smith, Richard F.; Bates, Alvin C.
In this experiment, p-anisaldehyde is converted to p-anisonitrile by a modification of the three-step aldehyde-nitrile synthesis of Smith and Walker.
Smith, Richard F.; Bates, Alvin C. J. Chem. Educ. 1969, 46, 174.
Synthesis |
Mechanisms of Reactions |
Addition Reactions |
Nucleophilic Substitution |
Elimination Reactions |
Catalysis
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
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
Bromination of alkanes: Experiment illustrating relative reactivities and synthetic utility  Warkentin, J.
The radical halogenation of alkanes lend themselves well to the teaching of basic material such as bond dissociation energies, potential energy profiles, enthalpy of reaction, activation energy, and reaction rate.
Warkentin, J. J. Chem. Educ. 1966, 43, 331.
Electrochemistry |
Alkanes / Cycloalkanes |
Rate Law |
Kinetics |
Synthesis |
Alkenes |
Mechanisms of Reactions |
Free Radicals
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
Natural product chemistry: Laboratory research approach for elementary organic courses  O'Connor, Rod
Describes a program designed to introduce macro, semi-micro, and micro techniques of organic chemistry of the types commonly employed in research in natural product chemistry or in biologically-related fields.
O'Connor, Rod J. Chem. Educ. 1965, 42, 492.
Natural Products |
Undergraduate Research |
Separation Science |
Chromatography |
Thin Layer Chromatography |
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
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
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
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
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
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
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
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
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
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
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
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
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 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 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
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
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
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