| Journal Articles: 85 results |
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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
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Percy Julian, Robert Robinson, and the Identity of Eserethole Addison Ault
The Nova production Percy JulianForgotten 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
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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
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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
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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 UVvis 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
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From the Research Bench to the Teaching Laboratory: Gold Nanoparticle Layering Maria Oliver-Hoyo and Ralph W. Gerber
The procedures presented here involve the synthesis of gold colloidal suspensions, attachment of a functional group to glass with subsequent creation of self-assembled monolayers through deposition of gold nanoparticles, and measurements of wavelengths, absorbance, and conductivity.
Oliver-Hoyo, Maria; Gerber, Ralph W. J. Chem. Educ. 2007, 84, 1174.
Nanotechnology |
Surface Science |
Synthesis |
UV-Vis Spectroscopy
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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
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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
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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
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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
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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
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Creatine Synthesis: An Undergraduate Organic Chemistry Laboratory Experiment Andri L. Smith and Paula Tan
Describes the synthesis of creatine monohydratea popular supplement used in sports requiring short bursts of energyfor introductory organic chemistry laboratory courses. The synthesis illustrates the electrophilic nature of nitriles, as well as the nucleophilic nature of amines.
Smith, Andri L.; Tan, Paula. J. Chem. Educ. 2006, 83, 1654.
Amines / Ammonium Compounds |
Aqueous Solution Chemistry |
Bioorganic Chemistry |
Chromatography |
Dyes / Pigments |
Mechanisms of Reactions |
Microscale Lab |
Thin Layer Chromatography
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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
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Reductive Amination: A Remarkable Experiment for the Organic Laboratory Kim M. Touchette
The synthesis of N-(2-hydroxy-3-methoxybenzyl)-N-p-tolylacetamide is a fast, simple three-step sequence that serves as a useful example of the reductive amination reaction for the organic chemistry laboratory.
Touchette, Kim M. J. Chem. Educ. 2006, 83, 929.
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Green Chemistry |
Instrumental Methods |
IR Spectroscopy |
NMR Spectroscopy |
Oxidation / Reduction |
Solids
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The Discovery and Development of Cisplatin Rebecca A. Alderden, Matthew D. Hall, and Trevor W. Hambley
Cisplatin is currently one of the most widely used anticancer drugs in the world. The unlikely events surrounding the discovery of its anticancer activity, subsequent introduction into the clinic, and the continuing research into platinum compounds is the subject of this review.
Alderden, Rebecca A.; Hall, Matthew D.; Hambley, Trevor W. J. Chem. Educ. 2006, 83, 728.
Bioinorganic Chemistry |
Coordination Compounds |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Metallic Bonding |
Oxidation State |
Synthesis
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Preparation, Analysis, and Characterization of Some Transition Metal Complexes—A Holistic Approach Kristy M. Blyth, Lindsay R. Mullings, David N. Phillips, David Pritchard, and Wilhelm van Bronswijk
In this laboratory procedure, a wide range of complexes are characterized by IR and UVvis spectroscopy, magnetochemistry, and conductance. The results allow one to the deduce the nature and strength of the bonding of the ligand to the central atom and the number of ions that the complex produces in aqueous solution.
Blyth, Kristy M.; Mullings, Lindsay R.; Phillips, David N.; Pritchard, David; van Bronswijk, Wilhelm. J. Chem. Educ. 2005, 82, 1667.
IR Spectroscopy |
Magnetic Properties |
UV-Vis Spectroscopy |
Coordination Compounds |
Qualitative Analysis |
Synthesis |
Conductivity
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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
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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 structurefunction 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
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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 GCMS. 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
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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
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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
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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
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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
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"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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
|
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
|
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
|
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
|
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
|
Catalytic Transfer Hydogenation Reactions for Undergraduate Practical Programs R. W. Hanson
A brief review of catalytic transfer hydrogenation (CTH) reactions is given. Attention is drawn, particularly, to the utility of ammonium formate as the hydrogen donor in this type of reaction.
Hanson, R. W. J. Chem. Educ. 1997, 74, 430.
Catalysis |
Aldehydes / Ketones |
Alcohols |
Amines / Ammonium Compounds |
Mechanisms of Reactions
|
Microscale Electrophilic Aromatic Substitution of p-Toluidine Kady, Ismail O.
Experimental procedure for first-year organic chemistry students to apply the principles of group protection and study the effect of ring substituents on reaction orientation.
Kady, Ismail O. J. Chem. Educ. 1995, 72, A9.
Synthesis |
Mechanisms of Reactions |
Aromatic Compounds |
Microscale Lab |
Electrophilic Substitution
|
Microscale Preparation of AlCl3 Arnaiz, Francisco J.
Experimental procedure for producing anhydrous AlCl3 (aluminum chloride).
Arnaiz, Francisco J. J. Chem. Educ. 1995, 72, A8.
Synthesis |
Laboratory Management |
Microscale Lab
|
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
|
Synthesis of 1,1,1,3,3,3-Hexachloro-2,4-diisobutylcyclodiphosphaz(V)ane: An Inorganic Experiment Tillman, Christopher; Wood, Gary L.; Hampton, Michael
Procedure for synthesizing a main group ring system.
Tillman, Christopher; Wood, Gary L.; Hampton, Michael J. Chem. Educ. 1995, 72, 547.
Synthesis
|
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
|
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
|
Synthesis and Spectroscopic Study of Plant Growth Regulators Phenylpyridylureas: An "Agrorganic" Undergraduate Laboratory Experiment Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette
This lab could represent an undergraduate comparative synthesis and analysis of biologically active molecules, suitable for an introductory lab session.
Hocquet, Alexandre; Tohier, Jacques; Fournier, Josette J. Chem. Educ. 1994, 71, 1092.
Agricultural Chemistry |
Drugs / Pharmaceuticals |
Aldehydes / Ketones |
Aromatic Compounds |
Synthesis
|
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
|
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 and reactions of benzofurazan-1-oxide. Terrian, Deborah L.; Houghtaling, Melissa A.; Ames, James R.
An elementary experiment that can be used to familiarize students with the synthesis and reactions of nitrogen heterocycles.
Terrian, Deborah L.; Houghtaling, Melissa A.; Ames, James R. J. Chem. Educ. 1992, 69, 589.
Synthesis |
Heterocycles |
Aromatic Compounds
|
Corn chip aroma: A classroom demonstration on the preparation of a Schiff base Sartori, Antony T.; Wood, William F.
Preparing 3-methylimino-2-butanone.
Sartori, Antony T.; Wood, William F. J. Chem. Educ. 1992, 69, 572.
Aldehydes / Ketones |
Synthesis |
Reactions |
Mechanisms of Reactions
|
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
|
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 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
|
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
|
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
|
Microscale synthesis of heterocyclic compounds Al-awar, Rima; Wahl, George H., Jr.
The authors describe microscale syntheses of four heterocyclic compounds for which large-scale versions were described previously in this Journal.
Al-awar, Rima; Wahl, George H., Jr. J. Chem. Educ. 1990, 67, 265.
Microscale Lab |
Heterocycles |
Esters |
Aromatic Compounds |
Synthesis
|
The preparation of Indanthrene Scarlet GG: A vat dye experiment for the introductory organic chemistry laboratory Lutz, Wilson B.
The vat dye Indanthrene Scarlet GG can easily be synthesized and applied to cloth within a single two hour laboratory period.
Lutz, Wilson B. J. Chem. Educ. 1990, 67, 71.
Synthesis |
Dyes / Pigments |
Alkenes
|
Coordination complexes of cobalt: Inorganic synthesis in the general chemistry laboratory Williams, Gregory M.; Olmstead, John, III; Breksa, Andrew P., III
An experiment involving synthesis and spectral studies of a series of [Co(NH3)5L] complexes that introduces general chemistry students to inorganic synthesis and allows them to conduct a systematic study on the effect of different ligands on absorption spectra.
Williams, Gregory M.; Olmstead, John, III; Breksa, Andrew P., III J. Chem. Educ. 1989, 66, 1043.
Coordination Compounds |
Synthesis |
Spectroscopy
|
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
|
Synthesis of cobalt(III) "cage" complexes: A twist on an old theme in the inorganic laboratory Gahan, Lawrence R.; Healy, Peter C.; Patch, Graeme J.
The synthesis described for this compound is particularly attractive as an undergraduate experiment because the complex crystallizes from solution during the preparation removing the necessity of extensive and time-consuming chromatographic purification, which typifies most of these syntheses.
Gahan, Lawrence R.; Healy, Peter C.; Patch, Graeme J. J. Chem. Educ. 1989, 66, 445.
Synthesis
|
The synthesis of methyl salicylate: Amine diazotization. Zanger, Murray; McKee, James R.
Unlike many organic chemistry labs, this experiment does not expose students to carcinogenics, nor does it smell bad.
Zanger, Murray; McKee, James R. J. Chem. Educ. 1988, 65, 1106.
Amines / Ammonium Compounds |
Aromatic Compounds
|
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
|
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 testing of the insecticide carbaryl Thadeo, Peter F.; Mowery, Dwight F.
Carbaryl, 1-naphthyl-N-methylcarbamate, is synthesized from alpha-naphthol and triethylamine.
Thadeo, Peter F.; Mowery, Dwight F. J. Chem. Educ. 1984, 61, 742.
Synthesis |
Applications of Chemistry |
Aromatic Compounds |
Amines / Ammonium Compounds
|
An experiment on isomerism in metal-amino acid complexes: Preparation and characterization of cobalt(III) complexes containing N-bonded monodentate, O-bonded monodentate and N,O-chelated glycine ligands Harrison, R. Graeme; Nolan, Kevin B.
Synthesis of three cobalt(III) complexes that illustrate three possible modes of bonding of glycine to a metal ion, as well as methods for distinguishing among the products.
Harrison, R. Graeme; Nolan, Kevin B. J. Chem. Educ. 1982, 59, 1054.
Stereochemistry |
Amino Acids |
Coordination Compounds |
Synthesis |
Diastereomers |
IR Spectroscopy |
Crystal Field / Ligand Field Theory
|
Speeding up the inorganic lab: How fast is too fast? Sharrock, Patrick
Hydrogen peroxide can be used for speeding up the preparation of cobalt(III) complexes if the solutions are heated to complete the reaction.
Sharrock, Patrick J. Chem. Educ. 1980, 57, 778.
Synthesis
|
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
|
Phase transfer catalysis: An interim project Reeves, W. Preston
The authors have found that experiments in phase transfer catalysis provide students with a very profitable interim project.
Reeves, W. Preston J. Chem. Educ. 1978, 55, 433.
Catalysis |
Amines / Ammonium Compounds |
Separation Science
|
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
|
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
|
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
|
The preparation of 3-phenylanthranil. A sequential experiment for the undergraduate organic laboratory Kenny, David H.; Strieter, Jeffrey C.
A sequence of reactions that can be completed by the average student over ten weeks and involves a Friedel-Crafts reaction and Hofmann rearrangement.
Kenny, David H.; Strieter, Jeffrey C. J. Chem. Educ. 1972, 49, 130.
Synthesis |
Reactions
|
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
|
Acid hydrolysis of nylon 66 Berkowitz, W. F.
Presents a procedure for the hydrolysis of nylon 66.
Berkowitz, W. F. J. Chem. Educ. 1970, 47, 536.
Polymerization |
Synthesis
|
The Eschweiler-Clark methylation of amines: An organic chemistry experiment Pine, Stanley H.
In this procedure, benzylamine is converted to N,N-dimethylbenzylamine.
Pine, Stanley H. J. Chem. Educ. 1968, 45, 118.
Amines / Ammonium Compounds |
Synthesis
|
The amine catalyzed Perkin condensation: A class project Ketcham, Roger
In this exercise students carry out the amine catalyzed Perkin condensations of substituted benzaldehydes with substituted phenylacetic acids to give alpha-phenyl-cis- and trans-cinnamic acids.
Ketcham, Roger J. Chem. Educ. 1964, 41, 565.
Amines / Ammonium Compounds |
Catalysis |
Reactions |
Synthesis
|
Uses of electrical discharges in preparative inorganic chemistry Massey, Alan G.
Examines the preparation of some unusual compounds using glow discharge at low pressure, silent electric discharge, and microwave discharge.
Massey, Alan G. J. Chem. Educ. 1963, 40, 311.
Synthesis |
Electrochemistry
|
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
|
A separation and identification experiment for elementary organic chemistry laboratory Laughton, Paul M.
The student selects a test tube containing two unknowns and is told only that they have been selected from two of three possible groups: a primary or tertiary amine, an aldehyde or ketone, and an acid or phenol. The components are to be separated, their physical properties determined, their categories assigned, and one specific derivative prepared for each.
Laughton, Paul M. J. Chem. Educ. 1960, 37, 133.
Separation Science |
Qualitative Analysis |
Amines / Ammonium Compounds |
Aldehydes / Ketones |
Acids / Bases |
Phenols |
Physical Properties |
Synthesis
|
The preparation of "2-bromo-naphthalene" Wolfe, Winthrop C.; Doukas, Harry M.
Presents a procedure for the preparation of "2-bromo-naphthalene" in large or small amounts.
Wolfe, Winthrop C.; Doukas, Harry M. J. Chem. Educ. 1951, 28, 472.
Synthesis |
Alkenes
|
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