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Journal Articles: 240 results
[#96] Fun with Fingerprints: Cyanoacrylate Fuming  Anastasios Nikitakis and Karaliota A. Lymperopoulou
Students use cyanoacrylate fuming to render visible fingerprints on different surfaces and investigate the effects of changing the temperature and humidity of the fuming chamber.
Nikitakis, Anastasios; Lymperopoulou, Karaliota A. J. Chem. Educ. 2008, 85, 816A.
Applications of Chemistry |
Esters |
Forensic Chemistry |
Polymerization
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
Representing Fractional Distributions in Chemistry  Addison Ault
The purpose of this paper is to present a common approach to the representation of all forms of fractional distributions. Using a common approach is simple, easy to understand, and can reveal otherwise hidden relationships between phenomena.
Ault, Addison. J. Chem. Educ. 2008, 85, 1432.
Acids / Bases |
Amino Acids |
Carboxylic Acids |
Enzymes |
Kinetics |
Reactions
The Comparative Nucleophilicity of Naphthoxide Derivatives in Reactions with a Fast-Red TR Dye  Cheryl M. Mascarenhas
In this experiment, organic chemistry students perform reactions between three naphthyl acetate derivatives and the diazonium salt Fast-Red TR. Students discover under what conditions the hydrolysis and electrophilic aromatic substitution is fastest and slowest, allowing them to conclude that latter, rather than the former, is rate-limiting.
Mascarenhas, Cheryl M. J. Chem. Educ. 2008, 85, 1271.
Alcohols |
Aromatic Compounds |
Dyes / Pigments |
Esters |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography |
UV-Vis Spectroscopy
The Preparation and Enzymatic Hydrolysis of a Library of Esters  Elizabeth M. Sanford and Traci L. Smith
In this investigative case study, students work collaboratively to prepare and characterize a library of esters using Fischer esterification and alcoholysis of acid chlorides and their subsequent enzymatic hydrolysis by pig liver and orange peel esterases.
Sanford, Elizabeth M.; Smith, Traci L. J. Chem. Educ. 2008, 85, 944.
Drugs / Pharmaceuticals |
Enzymes |
Esters |
Industrial Chemistry |
IR Spectroscopy |
NMR Spectroscopy |
Synthesis |
Thin Layer Chromatography
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
[#96] Fun with Fingerprints: Cyanoacrylate Fuming  Anastasios Nikitakis and Karaliota A. Lymperopoulou
Students use cyanoacrylate fuming to render visible fingerprints on different surfaces and investigate the effects of changing the temperature and humidity of the fuming chamber.
Nikitakis, Anastasios; Lymperopoulou, Karaliota A. J. Chem. Educ. 2008, 85, 816A.
Applications of Chemistry |
Esters |
Forensic Chemistry |
Polymerization
Mosher Amides: Determining the Absolute Stereochemistry of Optically-Active Amines  Damian A. Allen, Anthony E. Tomaso, Jr., Owen P. Priest, David F. Hindson, and Jamie L. Hurlburt
In this experiment, teams of students are given an optically-pure amine of known structure but unknown stereochemistry. Different teams derivatize samples of the amine with (R) and (S) conformations of Mosher's acid chloride. The resulting diastereomers are analyzed by NMR to determine the absolute configuration of the initial, unknown amine.
Allen, Damian A.; Tomaso, Anthony E., Jr.; Priest, Owen P.; Hindson, David F.; Hurlburt, Jamie L. J. Chem. Educ. 2008, 85, 698.
Amides |
Chirality / Optical Activity |
Chromatography |
Diastereomers |
Microscale Lab |
NMR Spectroscopy |
Stereochemistry
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
Ring-Opening Polymerization of Lactide To Form a Biodegradable Polymer  Jennifer L. Robert and Katherine B. Aubrecht
In this laboratory, students carry out the tin(II) bis(2-ethylhexanoate)/benzyl alcohol mediated ring-opening polymerization of lactide to form the biodegradable polymer polylactide. As the mechanism of the polymerization is analogous to that of a transesterification reaction, the experiment can be used to demonstrate reactions of carboxylic acid derivatives.
Robert, Jennifer L.; Aubrecht, Katherine B. J. Chem. Educ. 2008, 85, 258.
Esters |
Green Chemistry |
NMR Spectroscopy |
Polymerization |
Stereochemistry
Biodiesel from Used Oil  Roland Stout
Recently three papers have appeared in this Journal discussing the properties of biodiesel fuels and their production from biological oils, either new or used. We will frustrate students if we do not discuss why laboratory scale productions of biodiesel from used oil may produce significant amounts of emulsion.
Stout, Roland. J. Chem. Educ. 2007, 84, 1765.
Esters |
Fatty Acids
A Guided-Inquiry Approach to the Sodium Borohydride Reduction and Grignard Reaction of Carbonyl Compounds  Robert E. Rosenberg
Students teams identify unknowns and their reaction products and use their data to deduce that esters are less electrophilic than the other carbonyl compounds present, that Grignard reagents are more nucleophilic than sodium borohydride, and that carboxylic acid derivatives do not undergo the nucleophilic addition reactions that are characteristic of aldehydes and ketones.
Rosenberg, Robert E. J. Chem. Educ. 2007, 84, 1474.
Addition Reactions |
Aldehydes / Ketones |
Esters |
Grignard Reagents |
IR Spectroscopy |
Oxidation / Reduction |
Reactions |
Student-Centered Learning
Oxidation of Aromatic Aldehydes Using Oxone  Rajani Gandhari, Padma P. Maddukuri, and Thottumkara K. Vinod
Describes an eco-friendly procedure for the oxidation of aldehydes to carboxylic acids in water or a water-ethanol mixture using Oxone as the oxidant. The use of eco-friendly solvents, a non-toxic reagent, and the elimination of extraction solvents in the procedure demonstrate important green chemistry themes to students.
Gandhari, Rajani; Maddukuri, Padma P.; Vinod, Thottumkara K. J. Chem. Educ. 2007, 84, 852.
Aldehydes / Ketones |
Aromatic Compounds |
Aqueous Solution Chemistry |
Carboxylic Acids |
Green Chemistry |
Mechanisms of Reactions |
NMR Spectroscopy |
Oxidation / Reduction
Sudoku Puzzles for First-Year Organic Chemistry Students  Alice L. Perez and G. Lamoureux
Sudoku puzzles are used to help the students learn the correspondence between the names of amino acids, their abbreviations, and codes; and the correspondence between the names of functional groups, their structures, and abbreviations.
Perez, Alice L.; Lamoureux, G. J. Chem. Educ. 2007, 84, 614.
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkylation |
Amines / Ammonium Compounds |
Amino Acids |
MO Theory |
Nomenclature / Units / Symbols |
Student-Centered Learning |
Alkynes |
Amides
Biodiesel Synthesis and Evaluation: An Organic Chemistry Experiment  Ehren C. Bucholtz
In this two week lab sequence students synthesize fatty acid methyl esters from simulated waste vegetable oil and determine whether the glycerol concentration of the resulting product is low enough to meet the specifications for marketable biodiesel.
Bucholtz, Ehren C. J. Chem. Educ. 2007, 84, 296.
Equilibrium |
Esters |
Industrial Chemistry |
Lipids |
Quantitative Analysis
Peer Review of Chemistry Journal Articles: Collaboration across Disciplines  Bozena Barbara Widanski and Debra Courtright-Nash
Organic chemistry students conducted self-designed experiments and submitted their manuscripts to English composition students who reviewed them according to journal guidelines. The results indicate that chemistry students improved their understanding of the scientific process and scientific writing.
Widanski, Bozena Barbara; Courtright-Nash, Debra. J. Chem. Educ. 2006, 83, 1788.
Esters |
Undergraduate Research |
Student-Centered Learning
Entropy and the Shelf Model: A Quantum Physical Approach to a Physical Property  Arnd H. Jungermann
A quantum physical approach relying on energy quantization leads to three simple rules which are the key to understanding the physical property described by molar entropy values.
Jungermann, Arnd H. J. Chem. Educ. 2006, 83, 1686.
Alcohols |
Alkanes / Cycloalkanes |
Carboxylic Acids |
Covalent Bonding |
Ionic Bonding |
Physical Properties |
Quantum Chemistry |
Thermodynamics
Using a Simulated Industrial Setting for the Development of an Improved Solvent System for the Recrystallization of Benzoic Acid: A Student-Centered Project  Timothy R. Hightower and Jay D. Heeren
Presents a peer-led, problem-solving organic laboratory exercise that provide students with an opportunity to produce a more efficient recrystallization solvent in an industrial environment.
Hightower, Timothy R.; Heeren, Jay D. J. Chem. Educ. 2006, 83, 1663.
Carboxylic Acids |
Industrial Chemistry |
Separation Science |
Solutions / Solvents
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
A Polymer in Everyday Life: The Isolation of Poly(vinyl alcohol) from Aqueous PVA Glues. An Undergraduate Chemistry Experiment   Yueh-Huey Chen and Jing-Fun Yaung
The IR spectra of three common and related polymers are used to identify functional groups and rationalize molecular structures.
Chen, Yueh-Huey; Yaung, Jing-Fun. J. Chem. Educ. 2006, 83, 1534.
Applications of Chemistry |
Aqueous Solution Chemistry |
Esters |
IR Spectroscopy |
Molecular Properties / Structure
Weak Acid pKa Determination Using Capillary Zone Electrophoresis  Mike Solow
In this experiment, students use capillary zone electrophoresis to determine the effective mobility of benzoic acid at two different hydrogen ion concentrations. A plot of these data yields the pKa of benzoic acid.
Solow, Mike. J. Chem. Educ. 2006, 83, 1194.
Acids / Bases |
Aqueous Solution Chemistry |
Carboxylic Acids |
Electrophoresis |
Instrumental Methods
Borodin  E. J. Behrman
Borodin made the first synthetic organic fluorine compound by reacting potassium hydrogen fluoride with benzoyl chloride to form benzoyl fluoride, a process known generally today as the Hunsdiecker reaction.
Behrman, E. J. J. Chem. Educ. 2006, 83, 1138.
Carboxylic Acids |
Acids / Bases |
Reactions |
Nutrition
The Synthesis of Copper(II) Carboxylates Revisited  Kevin Kushner, Robert E. Spangler, Ralph A. Salazar, Jr., and J. J. Lagowski
Describes an electrochemical synthesis of copper(II) carboxylates for use in the general chemistry laboratory course for chemistry majors.
Kushner, Kevin; Spangler, Robert E.; Salazar, Ralph A., Jr.; Lagowski, J. J. J. Chem. Educ. 2006, 83, 1042.
Carboxylic Acids |
Coordination Compounds |
Electrochemistry |
Metals |
Solutions / Solvents |
Transition Elements |
Undergraduate Research |
Synthesis
An Exploration of a Photochemical Pericyclic Reaction Using NMR Data  Sara M. Hein
This inexpensive, small-scale experiment for advanced organic students describes the unambiguous identification of a photochemical dimerization product from eleven possible candidates.
Hein, Sara M. J. Chem. Educ. 2006, 83, 940.
Addition Reactions |
Alkanes / Cycloalkanes |
Alkenes |
Carboxylic Acids |
Conformational Analysis |
NMR Spectroscopy |
Photochemistry |
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
Iodolactonization of 4-Pentenoic Acid   R. David Crouch, Alexander Tucker-Schwartz, and Kathryn Barker
Describes an experiment in which 4-pentenoic acid is converted into a lactone via iodolactonization.
Crouch, R. David; Tucker-Schwartz, Alexander; Barker, Kathryn. J. Chem. Educ. 2006, 83, 921.
Alkenes |
Carboxylic Acids |
IR Spectroscopy |
Mechanisms of Reactions |
NMR Spectroscopy |
Reactions |
Synthesis
Octachem Model: Organic Chemistry Nomenclature Companion  Joaquin Palacios
The Octachem model is an educational physical model designed to guide students in the identification, classification, and naming of the chemical structures of organic compounds. In this article the basic concepts of Octachem model are presented, and the physical model and contents are described.
Palacios, Joaquin. J. Chem. Educ. 2006, 83, 890.
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amines / Ammonium Compounds |
Esters |
Ethers |
Nomenclature / Units / Symbols
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
Ozonolysis Problems That Promote Student Reasoning  Ray A. Gross Jr.
The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.
Gross, Ray A., Jr. J. Chem. Educ. 2006, 83, 604.
Aldehydes / Ketones |
Alkenes |
Alkynes |
Carboxylic Acids |
Oxidation / Reduction |
Student-Centered Learning
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
Introduction to the Design and Optimization of Experiments Using Response Surface Methodology. A Gas Chromatography Experiment for the Instrumentation Laboratory  Patricia L. Lang, Benjamin I. Miller, and Abigail Tuttle Nowak
Describes a gas chromatography experiment, designed for the senior-level instrumental analysis laboratory, in which the students apply response surface methodology to determine the optimum set of chromatographic conditions required to separate four fatty acid methyl esters.
Lang, Patricia L.; Miller, Benjamin I.; Nowak, Abigail Tuttle. J. Chem. Educ. 2006, 83, 280.
Chemometrics |
Chromatography |
Esters |
Gas Chromatography |
Instrumental Methods |
Qualitative Analysis |
Fatty Acids
Determination of the Heat of Combustion of Biodiesel Using Bomb Calorimetry. A Multidisciplinary Undergraduate Chemistry Experiment  Stephen M. Akers, Jeremy L. Conkle, Stephanie N. Thomas, and Keith B. Rider
Over a three-week period, students synthesize biodiesel, measure its heat of combustion, density, and cloud point, then compare these properties to conventional petroleum diesel.
Akers, Stephen M.; Conkle, Jeremy L.; Thomas, Stephanie N.; Rider, Keith B. J. Chem. Educ. 2006, 83, 260.
Calorimetry / Thermochemistry |
Esters |
Green Chemistry |
Lipids |
Thermodynamics |
UV-Vis Spectroscopy
Preparation and Viscosity of Biodiesel from New and Used Vegetable Oil. An Inquiry-Based Environmental Chemistry Laboratory  Nathan R. Clarke, John Patrick Casey, Earlene D. Brown, Ezenwa Oneyma, and Kelley J. Donaghy
Presents a simple synthetic laboratory that requires students to find a general synthetic method to make biodiesel (fuel made from clean sources such as vegetable oils) and assess its viscosity versus temperature.
Clarke, Nathan R.; Casey, John Patrick; Brown, Earlene D.; Oneyma, Ezenwa; Donaghy, Kelley J. . J. Chem. Educ. 2006, 83, 257.
Applications of Chemistry |
Esters |
Physical Properties |
Synthesis
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
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
The Discovery-Oriented Approach to Organic Chemistry. 6. Selective Reduction in Organic Chemistry: Reduction of Aldehydes in the Presence of Esters Using Sodium Borohydride  Ashvin R. Baru and Ram S. Mohan
Describes two discovery oriented lab experiments involving the chemoselective reduction of vanillin acetate and methyl 4-formylbenzoate in the presence of esters using sodium borohydride, followed by product identification using 1H and 13C NMR spectroscopy.
Baru, Ashvin R.; Mohan, Ram S. J. Chem. Educ. 2005, 82, 1674.
NMR Spectroscopy |
Alcohols |
Aldehydes / Ketones |
Esters |
Oxidation / Reduction |
Thin Layer Chromatography |
Synthesis
Making Usable, Quality Opaque or Transparent Soap  Suzanne T. Mabrouk
First-year and organic chemistry students will learn the chemistry of soap by making some of the eleven described formulations, which produce usable, quality bars of soap. Opaque and transparent soaps are made in two and three hours, respectively. With an introduction to formulation chemistry, organic chemistry students can devise a formulation to synthesize their own opaque soap. Many of the formulations use commonly-available fats and oils, while some formulations incorporate specialty fats and oils for therapeutic purposes, for example, to relieve dry skin or itching.
Mabrouk, Suzanne T. J. Chem. Educ. 2005, 82, 1534.
Colloids |
Consumer Chemistry |
Lipids |
Nonmajor Courses |
Applications of Chemistry |
Esters
Synthesis and Physical Properties of Liquid Crystals: An Interdisciplinary Experiment  Gerald R. Van Hecke, Kerry K. Karukstis, Hanhan Li, Hansford C. Hendargo, Andrew J. Cosand, and Marja M. Fox
This experiment features an investigative approach designed for the introductory science or engineering major and integrates concepts in the fields of chemistry, biology, and physics. Derived from faculty research interests, this novel experiment gives students the opportunity to draw conclusions from tests performed to illustrate the connection between molecular structure and macroscopic properties. The chemical synthesis of the compounds studied further enhances the connection between molecular structure and macroscopic physical properties. The results of two separate physical measurements, refractometry and absorption spectroscopy, are combined to calculate a microscopic, but very practical, property of chiral nematic liquidsthe pitch of the helix formed in the liquid crystalline phase.
Van Hecke, Gerald R.; Karukstis, Kerry K.; Li, Hanhan; Hendargo, Hansford C.; Cosand, Andrew J.; Fox, Marja M. J. Chem. Educ. 2005, 82, 1349.
Chirality / Optical Activity |
Crystals / Crystallography |
Molecular Properties / Structure |
UV-Vis Spectroscopy |
Acids / Bases |
Esters |
Physical Properties |
Physical Properties
Application of ChemDraw NMR Tool: Correlation of Program-Generated 13C Chemical Shifts and pKa Values of para-Substituted Benzoic Acids  Hongyi Wang
An application of ChemDraw NMR Tool was demonstrated by correlation of program-generated 13C NMR chemical shifts and pKa values of para-substituted benzoic acids. Experimental 13C NMR chemical shifts were analyzed in the same way for comparison. The project can be used as an assignment at the end of the first-year organic chemistry course to review topics or explore new techniques: Hammett equation, acidbase equilibrium theory, electronic nature of functional groups, inductive and resonance effects, structurereactivity relationship, NMR spectroscopy, literature search, database search, and ChemDraw software.
Wang, Hongyi. J. Chem. Educ. 2005, 82, 1340.
Acids / Bases |
Equilibrium |
NMR Spectroscopy |
Aqueous Solution Chemistry |
Carboxylic Acids
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
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
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
Acid–Base and Precipitation Equilibria in Wine  Miguel Palma and Carmelo G. Barroso
A simple but effective experiment demonstrates the interactions between simultaneous equilibria involving hydrogen tartrate and helps students realize the importance of multiple equilibria in real-world systems.
Palma, Miguel; Barroso, Carmelo G. J. Chem. Educ. 2004, 81, 94.
Acids / Bases |
Aqueous Solution Chemistry |
Consumer Chemistry |
Food Science |
Alcohols |
Carboxylic Acids
Stearic Acid  Jay A. Young
Properties, hazards, and storage requirements for stearic acid.
Young, Jay A. J. Chem. Educ. 2004, 81, 25.
Laboratory Equipment / Apparatus |
Laboratory Management |
Carboxylic Acids |
Acids / Bases |
Physical Properties
Apple Fool! An Introduction to Artificial Flavors  
Investigation of flavoring by making artificial "cooked apples".
JCE Editorial Staff. J. Chem. Educ. 2003, 80, 408A.
Consumer Chemistry |
Food Science |
Esters |
Applications of Chemistry
Analytical Spectroscopy Using Modular Systems  Brian M. Patterson, Neil D. Danielson, Gary A. Lorigan, and André J. Sommer
This article describes the development of three analytical spectroscopy experiments that compare the determination of salicylic acid (SA) content in aspirin tablets. The experiments are based on UVvis, fluorescence, and Raman spectroscopies and utilize modular spectroscopic components. Students assemble their own instruments, optimize them with respect to signal-to-noise, generate calibration curves, determine the SA content in retail aspirin tablets, and assign features in the respective spectra to functional groups within the active material.
Patterson, Brian M.; Danielson, Neil D.; Lorigan, Gary A.; Sommer, André J. J. Chem. Educ. 2003, 80, 1460.
Fluorescence Spectroscopy |
Laboratory Equipment / Apparatus |
Quantitative Analysis |
Raman Spectroscopy |
UV-Vis Spectroscopy |
Aromatic Compounds |
Esters |
Carboxylic Acids |
Alcohols
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
Featured Molecules: Ascorbic Acid and Methylene Blue  William F. Coleman and Randall J. Wildman
Fully manipulable Chime versions of ascorbic acid and methylene blue, for the articles "Arsenic: Not So Evil After All?"; "Out of the Blue"; "Greening the Blue Bottle"; and "Sailing on the 'C': A Vitamin Titration with a Twist"
Coleman, William F.; Wildman, Randall J. J. Chem. Educ. 2003, 80, 584.
Molecular Modeling |
Molecular Properties / Structure |
Carboxylic Acids
Organic Functional Group Playing Card Deck  Michael J. Welsh
Organic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.
Welsh, Michael J. J. Chem. Educ. 2003, 80, 426.
Nomenclature / Units / Symbols |
Nonmajor Courses |
Enrichment / Review Materials |
Alcohols |
Aldehydes / Ketones |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Amides |
Amines / Ammonium Compounds |
Aromatic Compounds |
Carboxylic Acids |
Esters |
Ethers |
Mechanisms of Reactions |
Synthesis
"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
Featured Molecules: Enantiomers of Guaifenesin  William F. Coleman and Randall J. Wildman
Fully manipulable Chime versions of guaifenesin or 3-(2-methoxyphenoxy)-1,2-propanediol, an aromaric ether, for the article "Semi-Microscale Williamson Ether Synthesis and Simultaneous Isolation of an Expectorant from Cough Tablets"
Coleman, William F.; Wildman, Randall J. J. Chem. Educ. 2003, 80, 315.
Molecular Modeling |
Molecular Properties / Structure |
Aromatic Compounds |
Esters
C–H and C–D Bonds: An Experimental Approach to the Identity of C–H Bonds by Their Conversion to C–D Bonds  Alex T. Rowland
Three experiments that allow students to determine the relative reactivity of C-H bonds that are aliphatic, alpha, benzylic, or aromatic by the ease of substitution of deuterium for oxygen.
Rowland, Alex T. J. Chem. Educ. 2003, 80, 311.
Acids / Bases |
IR Spectroscopy |
Isotopes |
NMR Spectroscopy |
Undergraduate Research |
Alkanes / Cycloalkanes |
Aromatic Compounds |
Carboxylic Acids
1H NMR Measurement of the Trans–Cis Photoisomerization of Cinnamic Acid Derivatives  Basil Danylec and Magdy N. Iskander
Procedure that illustrates trans-cis photoisomerization.
Danylec, Basil; Iskander, Magdy N. J. Chem. Educ. 2002, 79, 1000.
NMR Spectroscopy |
Photochemistry |
Stereochemistry |
Aromatic Compounds |
Alcohols |
Esters |
Alkenes |
Molecular Properties / Structure
The Mechanism of the Ritter Reaction in Combination with Wagner-Meerwein Rearrangements. A Cooperative Learning Experience  María I. Colombo, María L. Bohn, and Edmundo A. Rúveda
Procedure in which students develop analytical and problem-solving skills by investigating an organic reaction mechanism, predicting the most likely products, and suggesting experiments to test the postulated mechanistic pathways and possible intermediates.
Colombo, María I.; Bohn, María L.; Rúveda, Edmundo A. J. Chem. Educ. 2002, 79, 484.
Mechanisms of Reactions |
Reactive Intermediates |
Amides |
Thin Layer Chromatography |
NMR Spectroscopy
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 Cis-Trans Equilibrium of N-Acetyl-L-Proline. An Experiment for the Biophysical Chemistry Laboratory  Kathryn R. Williams, Bhavin Adhyaru, Igor German, and Eric Alvarez
A cis-trans equilibrium system that demonstrates the effect of solvent polarity and aqueous pH.
Williams, Kathryn R.; Adhyaru, Bhavin; German, Igor; Alvarez, Eric. J. Chem. Educ. 2002, 79, 372.
Amino Acids |
Biophysical Chemistry |
NMR Spectroscopy |
Proteins / Peptides |
NMR Spectroscopy |
Amines / Ammonium Compounds |
Carboxylic Acids |
Equilibrium |
Stereochemistry |
Diastereomers
The Mechanism of Aqueous Hydrolysis of Nitro Derivatives of Phenyl Phenylmethanesulfonate. An Organic Laboratory Experiment  S. D. Mulder, B. E. Hoogenboom, and A. G. Splittgerber
Synthesis, purification, and characterization of three esters.
Mulder, S. D.; Hoogenboom, B. E.; Splittgerber, A. G. J. Chem. Educ. 2002, 79, 218.
Mechanisms of Reactions |
Molecular Properties / Structure |
Resonance Theory |
Reactive Intermediates |
Equilibrium |
Esters |
Aromatic Compounds |
Brønsted-Lowry Acids / Bases
Formic Acid  Jay A. Young
Properties, hazards, and storage requirements for formic acid.
Young, Jay A. J. Chem. Educ. 2002, 79, 157.
Acids / Bases |
Physical Properties |
Laboratory Management |
Carboxylic Acids
Soap from Nutmeg: An Integrated Introductory Organic Chemistry Laboratory Experiment  Marcio C. S. de Mattos and David E. Nicodem
A sequence of experiments in which trimyristin is extracted, isolated, and purified from nutmeg, then converted to a soap (sodium myristate) and acidified to produce myristic acid.
de Mattos, Marcio C. S.; Nicodem, David E. J. Chem. Educ. 2002, 79, 94.
Natural Products |
Carboxylic Acids |
Consumer Chemistry |
Fatty Acids
The Vitamin C Clock Reaction  Stephen W. Wright
Clock reaction using supermarket materials (vitamin C, hydrogen peroxide, tincture of iodine, and starch).
Wright, Stephen W. J. Chem. Educ. 2002, 79, 41.
Consumer Chemistry |
Oxidation / Reduction |
Vitamins |
Carboxylic Acids
pH of Sodium Acetate Solutions  Guy Schmitz
Example of buffering power in deviations of the pH of sodium acetate from calculated values.
Schmitz, Guy. J. Chem. Educ. 2002, 79, 29.
Acids / Bases |
Carboxylic Acids |
pH
Response to Potential-Energy-Only Models (re J. Chem. Educ. 2000, 77, 155-156)  Frank Rioux and Roger L. DeKock
Example of buffering power in deviations of the pH of sodium acetate from calculated values.
Rioux, Frank; DeKock, Roger L. J. Chem. Educ. 2002, 79, 29.
Acids / Bases |
Carboxylic Acids |
pH |
Atomic Properties / Structure |
Quantum Chemistry |
Theoretical Chemistry
The Combined Effects of pH and Percent Methanol on the HPLC Separation of Benzoic Acid and Phenol  Seema M. Joseph and John A. Palasota
Investigating the combined effects of pH and percent methanol on the HPLC separation of benzoic acid and phenol.
Joseph, Seema M.; Palasota, John A. J. Chem. Educ. 2001, 78, 1381.
Chromatography |
Instrumental Methods |
Separation Science |
Carboxylic Acids |
Aromatic Compounds |
Phenols
The Biginelli Reaction  Michael S. Holden and R. David Crouch
Procedure illustrating the Biginelli reaction.
Holden, Michael S.; Crouch, R. David. J. Chem. Educ. 2001, 78, 1104.
Microscale Lab |
Synthesis |
Reactions |
Mechanisms of Reactions |
Esters |
Heterocycles
Chemical Laboratory Information Profile: Acetic Acid (glacial)  Jay A. Young
Properties, hazards, and storage requirements for acetic acid (glacial).
Young, Jay A. J. Chem. Educ. 2001, 78, 721.
Acids / Bases |
Laboratory Management |
Physical Properties |
Carboxylic Acids
Molecular Mechanics and Variable-Temperature 1H NMR Studies on N,N-Diethyl-m-toluamide. An Undergraduate NMR and Molecular Modeling Experiment  Bruce L. Jensen and Raymond C. Fort Jr.
A combination of molecular modeling and variable-temperature NMR experiments is used to analyze the barrier to rotation about the amide bond of N,N-diethyl-m-toluamide (DEET). This approach utilizes the ability of computers to calculate the potential energy of a set of conformations obtained from a dihedral drive around the N-CO bond.
Jensen, Bruce L.; Fort, Raymond C. Jr. J. Chem. Educ. 2001, 78, 538.
Molecular Modeling |
Molecular Properties / Structure |
NMR Spectroscopy |
Amides
Determination of Lipophilicity Constants of Sulfonamide Substituents  Maria Auxiliadôra Fontes Prado
This article describes a simple laboratory activity using reversed-phase thin-layer chromatography (a stationary nonpolar phase and a mobile polar phase); the Rf values determined for sulfonamides by means of reversed-phase thin-layer chromatography are used to calculate the chromatographic parameter Rm and the lipophilicity constants (pi) of different substituent groups of sulfonamides.
Prado, Maria Auxiliadôra Fontes. J. Chem. Educ. 2001, 78, 533.
Chromatography |
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Amides
Simulating How a Virus Spreads through a Population: An Introduction to Acid-Base Chemistry in the Organic Chemistry Laboratory  Ronald M. Jarret
The traditional lab exercise that achieves separation of a mixture of 4-aminoacetophenone and benzoic acid by chemically active extraction has been expanded to include an exercise that uses materials from the extraction experiment to simulate how a virus spreads through a population.
Jarret, Ronald M. J. Chem. Educ. 2001, 78, 525.
Acids / Bases |
Separation Science |
Solutions / Solvents |
Aromatic Compounds |
Carboxylic Acids
Synthesis of Methyl 2,3,5-Tri-O-benzoyl-a-D-arabinofuranoside in the Organic Laboratory  Christopher S. Callam and Todd L. Lowary
Experiment to give students additional exposure to carbohydrate chemistry and provide an opportunity to discuss kinetic vs thermodynamic control of reactions, mutarotation, the synthesis of esters, recrystallization, the separation of diastereomers, and optical activity.
Callam, Christopher S.; Lowary, Todd L. J. Chem. Educ. 2001, 78, 73.
Carbohydrates |
Medicinal Chemistry |
NMR Spectroscopy |
Synthesis |
Kinetics |
Esters |
Diastereomers |
Chirality / Optical Activity |
Alcohols
Dog with Ball Joins Flying Bird
(re J. Chem. Educ. 1999, 76, 1656)  Richard S. Treptow
Comparing structural models to simple figures.
Treptow, Richard S. J. Chem. Educ. 2001, 78, 31.
Molecular Properties / Structure |
Carboxylic Acids |
Molecular Modeling
Organic Acids without a Carboxylic Acid Functional Group  G. V. Perez and Alice L. Perez
This paper presents several organic molecules that have been labeled as acids but do not contain a carboxylic acid functional group. Various chemical principles such as pKa, tautomerization, aromaticity, conformation, resonance, and induction are explored.
Perez, G. V.; Perez, Alice L. J. Chem. Educ. 2000, 77, 910.
Acids / Bases |
Molecular Properties / Structure |
Nomenclature / Units / Symbols |
Phenols |
Carboxylic Acids |
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 Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments  Chriss E. McDonald

McDonald, Chriss E. J. Chem. Educ. 2000, 77, 750.
Oxidation / Reduction |
Alcohols |
Esters |
Synthesis |
Mechanisms of Reactions
An Unexpected Event When Chymotrypsin Performs Its Physiological Role  Ivan G. Darvey
One of the events that occur during the chymotrypsin-catalyzed hydrolysis of proteins is an example of an exception to a rule of thumb taught in introductory organic chemistry courses, namely, that amides can't readily be converted to esters. If biochemistry teachers and the authors of textbooks of biochemistry commented on this unusual reaction, it would emphasize further the remarkable part chymotrypsin plays as a catalyst in carrying out its main perceived "physiological role".
Darvey, Ivan G. J. Chem. Educ. 2000, 77, 422.
Catalysis |
Enzymes |
Amides |
Esters
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
Amino Acids, Aromatic Compounds, and Carboxylic Acids: How Did They Get Their Common Names?  Sam H. Leung
This article provides a brief survey of the origins of the common names of some amino acids, aromatic compounds, and carboxylic acids.
Leung, Sam H. J. Chem. Educ. 2000, 77, 48.
Amino Acids |
Aromatic Compounds |
Nomenclature / Units / Symbols |
Carboxylic Acids
Applications of Biocatalysis to Industrial Processes  John T. Sime
The possibility of environmentally friendly chemical reactions carried out under mild conditions with high degrees of selectivity has proved attractive in developing manufacturing processes. A number of such reactions are discussed in the industrial context with examples of a variety of reaction types. All processes presented have been implemented in the production of commercial products and provide a feel for the versatility of this technology.
Sime, John T. J. Chem. Educ. 1999, 76, 1658.
Biotechnology |
Catalysis |
Chirality / Optical Activity |
Drugs / Pharmaceuticals |
Enzymes |
Proteins / Peptides |
Synthesis |
Industrial Chemistry |
Applications of Chemistry |
Amides |
Esters
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
"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
Chemiluminescence Demonstration Illustrating Principles of Ester Hydrolysis Reactions  Andrew G. Hadd, David W. Lehmpuhl, Laura R. Kuck, and John W. Birks
Peroxyoxalate chemiluminescence, the most efficient nonenzymatic chemiluminescence reaction known, is used to demonstrate mechanistic features of analogous ester hydrolysis reactions.
Hadd, Andrew G.; Lehmpuhl, David W.; Kuck, Laura R.; Birks, John W. J. Chem. Educ. 1999, 76, 1237.
Kinetics |
Photochemistry |
Mechanisms of Reactions |
Atomic Properties / Structure |
Esters
Preparation and Identification of Benzoic Acids and Benzamides: An Organic "Unknown" Lab  Douglass F. Taber, Jade D. Nelson, and John P. Northrop
The reaction of an unknown substituted benzene derivative with oxalyl chloride and aluminum chloride gives the acid chloride. Hydrolysis of the acid chloride gives the acid, and reaction of the acid with concentrated aqueous ammonia gives the benzamide. The equivalent weight of the acid can be determined by titration; given this information and the melting points of the acid and the benzamide, it is possible to deduce the structure of the initial unknown.
Taber, Douglass F.; Nelson, Jade D.; Northrop, John P. J. Chem. Educ. 1999, 76, 828.
Qualitative Analysis |
Aromatic Compounds |
Carboxylic Acids
Recycling Solvent Mixtures of Ethyl Acetate and Hexanes  Timothy J. Wilkinson
A method to recycle ethyl acetate-hexanes mixtures from thin-layer or column chromatography experiments is described. The procedure consists of co-distillation of the mixture followed by estimation of the composition by reference to an Rf vs percent composite graph. The mixture is then diluted with the appropriate solvent to achieve the desired composition.
Wilkinson, Timothy J. J. Chem. Educ. 1998, 75, 1640.
Chromatography |
Separation Science |
Solutions / Solvents |
Esters |
Alkanes / Cycloalkanes
Solving the Mystery of Fading Fingerprints with London Dispersion Forces  Doris R. Kimbrough and Ronald DeLorenzo
The fingerprints of the perpetrator are often not the only ones of importance in the collection of evidence. The fingerprints of the victim can be extremely important as well, and obtaining them when the victim is a child can be a tricky and frustrating endeavor.
Kimbrough, Doris R.; DeLorenzo, Ronald. J. Chem. Educ. 1998, 75, 1300.
Noncovalent Interactions |
Forensic Chemistry |
Esters |
Applications of Chemistry
A Modified Synthesis of the Insect Repellent DEET  Peter H. Knoess and Edward G. Neeland
In the preparation of the insect repellent DEET, lab procedures prepare the intermediate m-toluoyl chloride by heating m-toluic acid with thionyl chloride for times ranging from 15 to 45 minutes. The acid chloride is then worked up under Schotten-Baumann conditions to yield DEET.
Knoess, Peter H.; Neeland, Edward G. J. Chem. Educ. 1998, 75, 1267.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
Synthesis of Aspirin: A General Chemistry Experiment  John A. Olmsted III
An experiment is described that is suitable for the early portion of the laboratory in a general chemistry course and integrates organic examples. It is the two-step synthesis of aspirin starting from oil of wintergreen. The mechanism for this synthesis provides examples of three major classes of chemical reactions: hydrolysis, condensation, and proton transfer.
Olmsted, John A., III. J. Chem. Educ. 1998, 75, 1261.
Drugs / Pharmaceuticals |
Medicinal Chemistry |
Mechanisms of Reactions |
Aromatic Compounds |
Carboxylic Acids |
Aldehydes / Ketones
The Baker's Yeast Reduction of Keto-Esters in Organic Solvents: A One Week Research Project for Undergraduate Students   Michael North
An experiment has been designed which allows final year undergraduate students to carry out a mini-research project in one week and thus get a flavor of the joys and tribulations of conducting chemical research before they undertake a major research project. The experiment is an investigation into the reduction of alpha- or beta-keto esters using non-fermenting Baker's yeast in petroleum ether.
North, Michael. J. Chem. Educ. 1998, 75, 630.
Bioinorganic Chemistry |
Bioorganic Chemistry |
Enzymes |
Synthesis |
Stereochemistry |
Aldehydes / Ketones |
Esters |
Undergraduate Research
Synthesis of Exotic Soaps in the Chemistry Laboratory  Otto Phanstiel IV, Eric Dueno, and Queenie Xianghong Wang
A variety of different triglyceride sources ranging from Vietnamese garlic oil to a local restaurant's grill sludge were saponified to generate a series of exotic soaps. Students did not quantify their results, but described their products in terms of color, texture and odor.
Phanstiel, Otto, IV; Dueno, Eric; Wang, Queenie Xianghong. J. Chem. Educ. 1998, 75, 612.
Qualitative Analysis |
Carboxylic Acids |
Lipids |
Consumer Chemistry |
Applications of Chemistry |
Fatty Acids
Nucleophilic Addition vs. Substituion: A Puzzle for the Organic Laboratory  Ernest F. Silversmith
The chemistry of beta-carbonyl compounds is studied. Beta-carbonyl compounds react with hydrazines to give products with a 5-membered ring containing two nitrogens. The experiment makes students determine whether ethyl 2-acetyl-3-oxobutanoate reacts like a beta-diketone or like a beta-keto ester.
Silversmith, Ernest F. J. Chem. Educ. 1998, 75, 221.
Learning Theories |
Nucleophilic Substitution |
Aldehydes / Ketones |
Esters |
Mechanisms of Reactions
Assessing the Fate of Organic Contaminants in Aquatic Environments: Mechanism and Kinetics of Hydrolysis of a Carboxylic Ester  Jorg Klausen, Markus A. Meier , and Rene P. Schwarzenbach
An integrated experiment is proposed for an upper level undergraduate environmental chemistry laboratory. Using 2,4-dinitrophenylacetate (DNPA) as an example, the mechanisms of the abiotic hydrolysis of carboxylic esters are presented and the kinetic expressions are derived. The proposed experimental set-up uses isocratic reversed phase HPLC with UV detection to follow the decrease of DNPA concentration during hydrolysis experiments.
Klausen, Jorg; Meier, Markus A.; Schwarzenbach, Rene P. J. Chem. Educ. 1997, 74, 1440.
Kinetics |
Mechanisms of Reactions |
Chromatography |
Esters |
Water / Water Chemistry
Does Copper Metal React with Acetic Acid?  Stephen DeMeo
Starting with a discrepant event and led through a series of experiments, students of an introductory chemistry course investigate if copper metal reacts with acetic acid. Finding that oxygen from the air plays an important role in the reaction of these substances, students ultimately realize that the conditions under which two reactants interact are important in determining the type of products that are made.
DeMeo, Stephen. J. Chem. Educ. 1997, 74, 844.
Acids / Bases |
Aqueous Solution Chemistry |
Carboxylic Acids
Determination of the Enantiomeric Purity of Naproxen: An Organic Chemistry Laboratory Experiment  Thomas D. Walsh and Curtis S. Koontz
Recent availability of and publicity surrounding the antiinflammatory drug naproxen presents an opportunity for an organic chemistry laboratory experiment of great up-to-the-minute interest.
Walsh, Thomas D.; Koontz, Curtis S. . J. Chem. Educ. 1997, 74, 585.
Stereochemistry |
Drugs / Pharmaceuticals |
Molecular Properties / Structure |
Aromatic Compounds |
Carboxylic Acids
Reduction of Carboxylic Acids with Sodium Borohydride and an Electrophile  Jan William Simek, Thad Tuck, and Kelly Courter Bush
Integration of new reduction conditions into a procedure applicable to the first-year organic chemistry laboratory, where reduction of the carboxylic acid group has remained an obstacle, notwithstanding the use of borane or LiAlH4 (2) on the microscale. The NaBH4 method with either electrophile can be modified to any scale; in our hands, the use of I2 as the electrophile performed better at the semimicro scale than the H2SO4 method.
Simek, Jan William; Tuck, Thad; Bush, Kelly Courter . J. Chem. Educ. 1997, 74, 107.
Carboxylic Acids |
Aromatic Compounds |
Oxidation / Reduction
Regiospecific Ester Hydrolysis by Orange Peel Esterase - An Undergraduate Experiment.  Timothy D.H. Bugg, Andrew M. Lewin and Eric R. Catlin
The experiment involves the preparation of diester derivatives of para-, meta- and ortho-hydroxybenzoic acid (e.g. methyl 4-acetoxy-benzoic acid). The derivatives are incubated with orange peel esterase, as a crude extract, and with commercially available pig liver esterase and porcine pancreatic lipase. The enzymatic hydrolysis reactions are monitored by thin layer chromatography, revealing which of the two ester groups is hydrolysed, and the rate of the enzyme-catalysed reaction.
Bugg. Timothy D. H.; Lewin, Andrew M.; Catlin, Eric R. J. Chem. Educ. 1997, 74, 105.
Esters |
Catalysis |
Chromatography
An Organoleptic Laboratory Experiment  John M. Risley
Compounds in ten different classes of organic molecules that are used in the fragrance and food industry are provided to students. Students whiff the vapors of each compound and describe the organoleptic properties using a set of terms utilized in the fragrance and food industry. A set of questions guides students to an understanding of the relationship between structure of molecules and smell.
Risley, John M. J. Chem. Educ. 1996, 73, 1181.
Molecular Properties / Structure |
Consumer Chemistry |
Physical Properties |
Nonmajor Courses |
Alcohols |
Aldehydes / Ketones |
Amines / Ammonium Compounds |
Carboxylic Acids |
Esters |
Ethers |
Phenols
A Convenient Synthesis of the Tetrasubstituted Pyrrole: An Undergraduate Heterocyclic Laboratory Experiment  Patrik Kolar, Miha Tisler
A two-step synthesis of tetrasubstituted pyrroles from esters of a-amino acids has been applied as a simple undergraduate laboratory experiment, which illustrates the utility of amino acids in heterocyclic synthesis.
Kolar, Patrik; Tisler, Miha. J. Chem. Educ. 1996, 73, 986.
Amino Acids |
IR Spectroscopy |
Synthesis |
Heterocycles |
Esters
The Esterification of Trifluoroacetic Acid: A Variable Temperature NMR Kinetics Study  Thomas N. Gallaher, David A. Gaul, and Serge Schreiner
This paper describes an addition to a previously published experiment in which NMR is used to follow the kinetics of the reaction of trifluoroacetic acid with alcohols. A variable temperature accessory is used to determine the energy of activation and reaction order with respect to the alcohol concentration.
Gallaher, Thomas N.; Gaul, David A.; Schreiner, Serge. J. Chem. Educ. 1996, 73, 465.
Kinetics |
NMR Spectroscopy |
Alcohols |
Esters
Synthesis of Ethyl Salicylate Using Household Chemicals  Sally Solomon, Chinhyu Hur, Alan Lee, and Kurt Smith
Ethyl salicylate is synthesized, isolated, and characterized in a three-step process using simple equipment and household chemicals.
Solomon, Sally; Hur, Chinyu; Lee, Alan; Smith, Kurt. J. Chem. Educ. 1996, 73, 173.
Synthesis |
Aromatic Compounds |
Carboxylic Acids
GC/MS of Unknown Esters for Teaching MS Fragmentation Patterns: A Combination Organic Experiment for Esterifying Unknown Alcohols and Determining their Structures by GC/MS  Ernest C. McGoran, Cameron Melton, and Darren Taitch
Students work together in groups of three to match fragmentation rules with actual MS data to identify each of three different unknowns, assigned individually for the conversion of their acetates.
McGoran, Ernest C.; Melton, Cameron; Taitch, Darren. J. Chem. Educ. 1996, 73, 88.
Alcohols |
Esters |
Mass Spectrometry |
Gas Chromatography
An Efficient Microscale Procedure for the Preparation of 3,5-Dinitrobenzoates  Smith, Richard F.; Cristalli, Gaetano M.
Efficient and simple microscale preparation of 3,5-dinitrobenzoates.
Smith, Richard F.; Cristalli, Gaetano M. J. Chem. Educ. 1995, 72, A164.
Synthesis |
Qualitative Analysis |
Laboratory Management |
Microscale Lab |
Aromatic Compounds |
Esters
"Double Unknown " Microscale Preparation and COSY Analysis of an Unknown Ester:
An Introductory 2D-NMR Experiment   Stephen E. Branz, Robert G. Miele, Roy K. Okuda, and Daniel A. Straus
Proton NMR activity designed to highlight the power of the technique to analyze structures and not merely confirm the identity of known substances.
Branz, Stephen E.; Miele, Robert G.; Okuda, Roy K.; Straus, Daniel A. J. Chem. Educ. 1995, 72, 659.
NMR Spectroscopy |
Stereochemistry |
Alcohols |
Carboxylic Acids |
Esters
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
"Crack" - A High-Interest Compound Illustrating Important Concepts in General Chemistry  Hoyt, William
Using crack and cocaine as examples of amine acid-base chemistry.
Hoyt, William J. Chem. Educ. 1995, 72, 322.
Acids / Bases |
Enrichment / Review Materials |
Amines / Ammonium Compounds |
Esters
The Ritter Reaction: Trapping a Carbocation with a Nitrile  Crouch, R. David
An organic experiment involving the Ritter reaction that yields an unpredictable product.
Crouch, R. David J. Chem. Educ. 1994, 71, A200.
Mechanisms of Reactions |
Amides |
Amines / Ammonium Compounds
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
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
Small Scale Determination of the pKa Values for Organic Acids  Flash, Patrick
Determination and interpretation of the pKa values for a series of organic acids as a concrete example of the effect of structure on acid strength.
Flash, Patrick J. Chem. Educ. 1994, 71, A6.
Acids / Bases |
Molecular Properties / Structure |
Carboxylic Acids
Kinetic demonstration of chemospecific reactions involving salicylate esters and amines: An experiment for advanced undergraduate/postgraduate students   Lajis, Nordin H.; Khan, Mohammad Niyaz
An experiment that demonstrates chemical reactivity.
Lajis, Nordin H.; Khan, Mohammad Niyaz J. Chem. Educ. 1993, 70, A264.
Amines / Ammonium Compounds |
Esters |
UV-Vis Spectroscopy |
Reactions
A convenient method of esterification of fatty acids: An undergraduate organic laboratory experiment  Di Raddo, Pasquale
A convenient method of esterification of fatty acids for undergraduate organic chemistry lab.
Di Raddo, Pasquale J. Chem. Educ. 1993, 70, 1034.
Carboxylic Acids |
Esters |
Gas Chromatography |
NMR Spectroscopy |
Fatty Acids
Determining Hammett sigma and rho values: Improvements on a published student experiment  Hathaway, Bruce A.; Olesen, Bjorn
Modifications and improvements to laboratory experiments written for an organic chemistry lab text.
Hathaway, Bruce A.; Olesen, Bjorn J. Chem. Educ. 1993, 70, 953.
Esters |
Acids / Bases |
Kinetics |
Synthesis
Replacing mineral acids in the laboratory: Nafion-catalyzed dehydration and esterification  Doyle, Michael P.; Plummer, Benjamin F.
The advantage of Nafion is that unlike mineral acids, this perfluorinated ion-exchange polymer is a solid resin that can be handled without the safety hazards usually associated with strong acids.
Doyle, Michael P.; Plummer, Benjamin F. J. Chem. Educ. 1993, 70, 493.
Esters |
Laboratory Management
Kinetics of the hydrolysis of orthoesters: A general acid-catalyzed reaction. An undergraduate physical organic chemistry experiment using NMR to determine both rate constants of a two-route mechanism  Potts, Richard A.; Schaller, Ruth A.
As more advanced instrumentation is made available for use by undergraduates, suitable experiments are needed. Due to the great importance of NMR spectroscopy in chemistry, this experiment was developed to give students some experience in this area.
Potts, Richard A.; Schaller, Ruth A. J. Chem. Educ. 1993, 70, 421.
NMR Spectroscopy |
Mechanisms of Reactions |
Esters |
Catalysis
Quantitative analysis by FTIR: Thin films of copolymers of ethylene and vinyl acetate.  Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno.
Quantitation of coploymers of ethylene and vinyl acetate using FTIR.
Mathias, Lon J.; Hankins, Marie G.; Bertolucci, Craig M.; Grubb, Tina L.; Muthiah, Jeno. J. Chem. Educ. 1992, 69, A217.
IR Spectroscopy |
Fourier Transform Techniques |
Quantitative Analysis |
Alkenes |
Carboxylic Acids
A source of isomer-drawing assignments  Kjonaas, Richard A.
A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.
Kjonaas, Richard A. J. Chem. Educ. 1992, 69, 452.
Stereochemistry |
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Aldehydes / Ketones |
Ethers |
Esters |
Alkynes
Enhancing interest in organic chemistry. Part I. Relating redolence in organic chemistry class.  Smith, Terrill D.
The author supplies a list of compounds that can be passed around in class for students to guess their origin from an odor.
Smith, Terrill D. J. Chem. Educ. 1992, 69, 233.
Esters |
Aldehydes / Ketones |
Alcohols |
Phenols
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
Microscale resolution of racemic 1-phenylethylamine and chiral high performance liquid chromatography (HPLC) in undergraduate chemistry   Krumpolc, Miroslav
A standard experiment has been modified to incorporate microscale techniques and employ chiral high performance liquid chromatography to determine enantiomeric purity.
Krumpolc, Miroslav J. Chem. Educ. 1991, 68, A176.
Enantiomers |
Amides |
Diastereomers |
Physical Properties |
Microscale Lab
The microscopic protonation constants of N,N-dimethyl-1,3-propanediamine: An NMR titration experiment  Onasch, O. F.; Schwartz, H. M.; Aikens, D. A.; Bunce, S. C.
An NMR titration experiment examining microscopic protonation.
Onasch, O. F.; Schwartz, H. M.; Aikens, D. A.; Bunce, S. C. J. Chem. Educ. 1991, 68, 791.
Titration / Volumetric Analysis |
NMR Spectroscopy |
Amides |
pH |
Equilibrium
The malonic ester synthesis in the undergraduate laboratory  Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D.
The versatile reactions of diethyl malonate represent an important lecture topic in introductory organic courses, but are only rarely performed in the lab because of several problems associated with performing these reactions. These authors present a lab the circumvents some of the typical problems.
Hoogenboom, Bernard E.; Ihrig, Phillip J.; Langsjoen, Arne N.; Linn, Carol J.; Mulder, Stephen D. J. Chem. Educ. 1991, 68, 689.
Aromatic Compounds |
Aldehydes / Ketones |
Amino Acids |
Heterocycles |
Amides
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
Thermal decomposition of diacyl peroxides and peresters: An undergraduate laboratory experiment using infrared absorptions to monitor decomposition rates  Mosher, Michael D.; Vinson, Sandra; Connagahan, Jodi; Forsythe, Regina; Mosher, Melvyn W.
This paper describes a technique that addresses the important educational goal of adapting research techniques into the teaching laboratory.
Mosher, Michael D.; Vinson, Sandra; Connagahan, Jodi; Forsythe, Regina; Mosher, Melvyn W. J. Chem. Educ. 1991, 68, 510.
IR Spectroscopy |
Kinetics |
Esters |
Reactions
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
An internal comparison of the intermolecular forces of common organic functional groups: A thin-layer chromatography experiment  Beauvais, Robert; Holman, R. W.
Due to the latest trends in organic chemistry textbook content sequences, it has become desirable to develop an experiment that is rapid, simple, and general, that would compare and contrast the various functional group classes of organic molecules in terms of their relative polarities, dipole moments, and intermolecular forces of attraction.
Beauvais, Robert; Holman, R. W. J. Chem. Educ. 1991, 68, 428.
Alkanes / Cycloalkanes |
Alkenes |
Alcohols |
Carboxylic Acids |
Aldehydes / Ketones |
Esters |
Qualitative Analysis |
Thin Layer Chromatography |
Noncovalent Interactions |
Molecular Properties / Structure
A brief freshman experience in qualitative organic analysis  Griswold, John R.; Rauner, Richard A.
This is an experiment aimed at second semester non-major students. Because such courses attempt to cover so much material in so little time, laboratory experiences must be carefully thought out.
Griswold, John R.; Rauner, Richard A. J. Chem. Educ. 1991, 68, 418.
Nonmajor Courses |
Aldehydes / Ketones |
Alcohols |
Esters |
Phenols |
Qualitative Analysis
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
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
Calculation of equilibrium constant in esterification reactions  Sarlo, Edward; Svoronos, Paris; Kulas, Patricia
Procedure for measuring the equilibrium constant in esterification reactions.
Sarlo, Edward; Svoronos, Paris; Kulas, Patricia J. Chem. Educ. 1990, 67, 796.
Esters |
Alcohols |
Carboxylic Acids |
Equilibrium
Nucleophilic aromatic substitution: A microscale organic experiment  Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M.
This experiment demonstrates one feasible route in preparing ortho-substituted benzoic acids and is also an example of nucleophilic aromatic substitution chemistry.
Avila, Walter B.; Crow, Jeffrey L.; Utermoehlen, Clifford M. J. Chem. Educ. 1990, 67, 350.
Nucleophilic Substitution |
Aromatic Compounds |
Microscale Lab |
Carboxylic Acids
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
A kinetic and mechanistic study of the alkaline hydrolysis of ethyl acetoacetate by acid-base potentiometry: Determination of the pKa of the ester  Paredes, Rodrigo; Ocampo, Rogelio
This experiment illustrates the determination of the kinetic order for a simple reaction. This experiment was used with good results in a physical organic chemistry class by advanced undergraduate students.
Paredes, Rodrigo; Ocampo, Rogelio J. Chem. Educ. 1990, 67, 72.
Esters |
Kinetics |
Potentiometry |
Acids / Bases |
pH
Polarized light and rates of chemical reactions  Weir, John J.
This experiment provides the opportunity to introduce the principles of reaction kinetics, polarized light, and the chemistry of optically active compounds; the rate of the acid-catalyzed hydrolysis of sucrose to glucose and fructose is determined.
Weir, John J. J. Chem. Educ. 1989, 66, 1035.
Rate Law |
Kinetics |
Chirality / Optical Activity |
Carboxylic Acids
Illustrating the inductive effect on acid strength of carboxylic acids  Kolb, Kenneth E.; Kolb, Doris
The effect of various substituents on acid strength can be easily demonstrated using aqueous solutions of various carboxylic acids containing a suitable indicator.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1989, 66, 1034.
Acids / Bases |
Carboxylic Acids
Isomerization of dimethyl maleate to dimethyl fumarate: An undergraduate experiment utilizing high performance liquid chromatography  Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M.
Introduces students to liquid chromatography, the stereoisomerization of alkenes, certain aspects of free radical chemistry, and thermodynamics.
Ledlie, David B.; Wenzel, Thomas J.; Hendrickson, Susan M. J. Chem. Educ. 1989, 66, 781.
HPLC |
Mechanisms of Reactions |
Esters |
Stereochemistry |
Free Radicals |
Alkenes |
Thermodynamics
Reactions of borohydride in carboxylic acid media: A summary  Nutaitis, Charles F.
Sodium borohydride / carboxylic acid systems represent a paradox of reactivity; depending on the substrate being transformed and the method sued to mix the reagents, this methodology can lead to reaction media that are either more or less reactive than sodium borohydride itself.
Nutaitis, Charles F. J. Chem. Educ. 1989, 66, 673.
Carboxylic Acids |
Mechanisms of Reactions
The proton NMR spectrum of ascorbic acid: A relevant example of deceptively simple second-order behavior  Reid, R. Stephen
To dispel student misconceptions, the use of the proton NMR spectrum of asorbic acid in D20 as an example has proven very effective.
Reid, R. Stephen J. Chem. Educ. 1989, 66, 344.
NMR Spectroscopy |
Rate Law |
Carboxylic Acids |
Vitamins
Molecular modeling in organic chemistry: Correlating odors with molecular structure  Lipkowitz, Kenny B.
This paper presents a safe, inexpensive, and successful undergraduate laboratory exercise that incorporates computational chemistry.
Lipkowitz, Kenny B. J. Chem. Educ. 1989, 66, 275.
Molecular Modeling |
Computational Chemistry |
Esters
Determination of the relative rates of alkaline hydrolysis of esters by the method of competition  Paredes, Rodrigo; Gil, Jimmy; Ocampo, Pamela
A method is presented for further illustration of the electronic and steric factors in the saponification of selected groups of esters.
Paredes, Rodrigo; Gil, Jimmy; Ocampo, Pamela J. Chem. Educ. 1988, 65, 1109.
Esters |
Mechanisms of Reactions |
Kinetics
A synthesis of chrysanthemic ester: An undergraduate experiment  Kelly, Lawrence F.
Procedure for producing a mixture of cis- and trans-ethyl chrysanthemates.
Kelly, Lawrence F. J. Chem. Educ. 1987, 64, 1061.
Esters |
Synthesis |
Catalysis |
Diastereomers |
Stereochemistry
Ring opening and ring forming polymerizations: An organic and polymer laboratory experiment  Mathias, Lon J.; Viswnathan, Tito
Polymer synthesis involving ring-opening polymerization to yield a polyamide from oxazoline and cyclopolymerization of a diallylamine derivative to give a polymer containing pyrrolidine units.
Mathias, Lon J.; Viswnathan, Tito J. Chem. Educ. 1987, 64, 639.
Polymerization |
Synthesis |
Heterocycles |
Amides |
Mechanisms of Reactions
On a common graphical flaw in the carboxylic acid/alcohol relative acidity argument  McClard, Ronald W.
Why are carboxylic acids so much more acidic than aliphatic alcohols?
McClard, Ronald W. J. Chem. Educ. 1987, 64, 416.
Carboxylic Acids |
Alcohols |
Acids / Bases
The structure of bis(trimethylsilyl) amides: A multinuclear NMR project  Samples, Majorie S.; Yoder, Claude H.; Schaeffor, Charles D., Jr.
A project designed to illustrate the great value of observing nuclei other than 1H and 13C (29Si, 14N, 17O).
Samples, Majorie S.; Yoder, Claude H.; Schaeffor, Charles D., Jr. J. Chem. Educ. 1987, 64, 177.
Molecular Properties / Structure |
Amides |
NMR Spectroscopy
Introducing plastic in the laboratory: Synthesis of a plasticizer, dioctylphthalate and evaluation of its effects on the physical properties of polystyrenes  Caspar, A.; Gillois, J.; Guillerm, G.; Savignac, M.; Vo-Quang, L.
These authors are proposing a two-stage experimental approach that combines preparative organic chemistry and polymer characterization.
Caspar, A.; Gillois, J.; Guillerm, G.; Savignac, M.; Vo-Quang, L. J. Chem. Educ. 1986, 63, 811.
Esters |
Reactions |
IR Spectroscopy |
UV-Vis Spectroscopy |
NMR Spectroscopy |
Mass Spectrometry |
Thin Layer Chromatography
Selective oxidation in the presence of a heterocycle  Bowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R.
The process of weighing the advantages and disadvantages of various oxidation methods are presented in this paper.
Bowles, K. Dean; Quincy, David A.; McKenna, John I.; Natale, N. R. J. Chem. Educ. 1986, 63, 358.
Alcohols |
Aldehydes / Ketones |
Heterocycles |
Oxidation / Reduction |
Carboxylic Acids
Catalysis of the carbonylation of alcohols to carboxylic acids including acetic acid synthesis from methanol  Forster, Denis; Dekleva, Thomas W.
These authors outline the fundamental aspects of the acetic acid process and suggest ways of extending the sythesis to higher carboxylic acids.
Forster, Denis; Dekleva, Thomas W. J. Chem. Educ. 1986, 63, 204.
Acids / Bases |
Alcohols |
Carboxylic Acids |
Alcohols |
Industrial Chemistry
The preparation of benzoyl esters of phenols and benzoic anhydride by phase-transfer catalysis  Yeadon, A.; Turney, T. A.; Ramsay, G.
The procedure is sufficiently rapid to replace the Schotten-Baumann technique.
Yeadon, A.; Turney, T. A.; Ramsay, G. J. Chem. Educ. 1985, 62, 518.
Synthesis |
Catalysis |
Esters |
Phenols |
Aromatic Compounds
Buffer capacity of various acetic acid-sodium acetate systems: A lecture experiment  Donahue, Craig J.; Panek, Mary G.
Uses indicators to illustrate the response of two buffers with the same initial pH value but differing buffer capacities.
Donahue, Craig J.; Panek, Mary G. J. Chem. Educ. 1985, 62, 337.
Acids / Bases |
pH |
Dyes / Pigments |
Aqueous Solution Chemistry |
Carboxylic Acids
A problem on formulas  Browne, Elaine J.
A problem suitable as an indicator of abstract thought and as an aid in selecting students for admission to honors or advanced placement courses.
Browne, Elaine J. J. Chem. Educ. 1985, 62, 242.
Carboxylic Acids
A short set of 13C-NMR correlation tables  Brown, D. W.
The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.
Brown, D. W. J. Chem. Educ. 1985, 62, 209.
NMR Spectroscopy |
Molecular Properties / Structure |
Alkanes / Cycloalkanes |
Alkenes |
Alkynes |
Aromatic Compounds |
Amides |
Carboxylic Acids |
Esters
L-amino acid ethyl ester hydrochlorides: Derivatives for qualitative organic analysis  Borders, C. L., Jr.; Blech, Dianne M.; McElvany, Karen D.
Results in the attempted synthesis of the ethyl ester hydrochlorides for 21 common L-amino acids to be provided to students for determination as unknowns.
Borders, C. L., Jr.; Blech, Dianne M.; McElvany, Karen D. J. Chem. Educ. 1984, 61, 814.
Amino Acids |
Esters |
Qualitative Analysis
To space or not to space- that is the question  Hurd, Charles D.
The use of spaces in the words "chloro acids" and "keto esters".
Hurd, Charles D. J. Chem. Educ. 1984, 61, 667.
Nomenclature / Units / Symbols |
Acids / Bases |
Esters
Synthesis of benzoic acid using household bleach  Perkins, Robert
Conversion of acetophenone to benzoic acid (the haloform reaction) using household bleach.
Perkins, Robert J. Chem. Educ. 1984, 61, 551.
Synthesis |
Carboxylic Acids |
Aromatic Compounds
A new method for the preparation of derivatives of carboxylic acids  Brindle, Ian D.; Chassie, Susan
Preparation technique using potassium fluoride. From the "State-of-the-Art Symposium for Chemical Educators: Chemistry of the Food Cycle".
Brindle, Ian D.; Chassie, Susan J. Chem. Educ. 1984, 61, 347.
Synthesis |
Carboxylic Acids
Gas chromatographic verification of a mathematical model: product distribution following methanolysis reactions  Lam, R. B.; Palocsay, F. A.; Gallaher, T. N.; Leary, J. J.
The work in this article demonstrates the applicability of the binomial distribution as a mathematical model the chemical equilibrium of bifunctional esters. The model as developed enables a straightforward extension to symmetrical polyfunctional esters and presents a mathematical basis for estimating equilibrium constants for such systems.
Lam, R. B.; Palocsay, F. A.; Gallaher, T. N.; Leary, J. J. J. Chem. Educ. 1983, 60, 769.
Esters |
Equilibrium |
Chemometrics
Application of aromatic solvent induced shifts in organic chemistry  Kalyanam, Nagabushanam
This article illustrates the predictability of the movement of proton signals in the case of carbonyl compounds when the solvent is changed from a standard aliphatic solvent to an aromatic solvent.
Kalyanam, Nagabushanam J. Chem. Educ. 1983, 60, 635.
Aromatic Compounds |
Carboxylic Acids |
NMR Spectroscopy |
Solutions / Solvents
A quick and simple conversion of carboxylic acids into their anilides of heating with phenyl isothiocyanate  Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K.
In this article, the authors report a quick and easy procedure using phenyl isothiocyanate, which is ideally suited to students.
Ram, Ram N.; Kumar, Pradeep; Mukerjee, Arya K. J. Chem. Educ. 1983, 60, 508.
Carboxylic Acids |
Aromatic Compounds |
Phenols |
Reactions
A chemistry laboratory project to develop thinking and writing skills  Goodman, W. Daniel; Bean, John C.
The "Ester Project" requires students to carry out an independent investigation of the synthesis of one or more alphatic esters and to present their research in the form of professional papers. The students, as a group, judge each paper for the quality of research and the quality of writing according to criteria and methods devised jointly by the students and the instructor.
Goodman, W. Daniel; Bean, John C. J. Chem. Educ. 1983, 60, 483.
Alcohols |
Esters
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
Kinetics of imidazole catalyzed ester hydrolysis: Use of buffer dilutions to determine spontaneous rate, catalyzed rate, and reaction order  Lombardo, Anthony
Uses the hydrolysis of p-nitro-phenyl acetate in the presence of imidazole to extract rate constants for a reaction proceeding by a catalyzed and uncatalyzed pathway simultaneously.
Lombardo, Anthony J. Chem. Educ. 1982, 59, 887.
Kinetics |
Catalysis |
Esters |
Rate Law
Richard Anschutz (1852-1937), Kekule's forgotten successor Part II: The work  Kauffman, George B.
In his mistaken attempt to prove that maleic and fumaric acids are structural rather than geometric isomers, Anschutz carried out much useful work not only on these compounds but also on many polybasic acids and their derivatives.
Kauffman, George B. J. Chem. Educ. 1982, 59, 745.
Carboxylic Acids |
Stereochemistry |
Diastereomers |
Acids / Bases |
Molecular Properties / Structure
The oxidation of terminal alkenes by permanganate: A practical demonstration of the use of phase transfer agents  Brown, Keith C.; Chang, Victor S.; Dar, Fazal H.; Lamb, Shannon E.; Lee, Donald G.
An oxidative cleavage of a terminal alkene to give the corresponding carboxylic acid with one less carbon atom.
Brown, Keith C.; Chang, Victor S.; Dar, Fazal H.; Lamb, Shannon E.; Lee, Donald G. J. Chem. Educ. 1982, 59, 696.
Alkenes |
Oxidation / Reduction |
Carboxylic Acids
The principle of vinylogy  Krishnamurthy, Subrahmanya
The principle of vinylogy recognizes the possibility that the inductive effect of a functional group is transmitted through a double bond or a conjugated system of double bonds.
Krishnamurthy, Subrahmanya J. Chem. Educ. 1982, 59, 543.
Molecular Properties / Structure |
Alkenes |
Esters |
Aldehydes / Ketones |
Amides |
Aromatic Compounds
Entropy and equilibria: A reassessment of ionization data for substituted acetic acids  Edward, John T.
Investigating the effect of various substituents on the proton-transfer reaction of substituted acetic acids in the gas phase and in water.
Edward, John T. J. Chem. Educ. 1982, 59, 354.
Thermodynamics |
Carboxylic Acids |
Acids / Bases |
Aqueous Solution Chemistry |
Equilibrium |
Gases
High performance liquid chromatography of vitamin A  Bohman, Ove; Engdahl, Kjell-Ake; Johnsson, Hakan
This experiment involves the quantitative determination of vitamin A in food products by analytival liquid chromatography and offers training both in work-up procedures and in the quantitative transfer of very small amounts of material.
Bohman, Ove; Engdahl, Kjell-Ake; Johnsson, Hakan J. Chem. Educ. 1982, 59, 251.
HPLC |
Chromatography |
Vitamins |
Quantitative Analysis |
Esters |
Fatty Acids
Using the equilibrium concept   Mickey, Charles D.
Equilibrium in systems is an important concept in organic, biochemical, and industrial chemistry among others.
Mickey, Charles D. J. Chem. Educ. 1981, 58, 56.
Biophysical Chemistry |
Equilibrium |
Esters |
Molecular Biology |
Kinetics |
Oxidation / Reduction |
Aqueous Solution Chemistry
Esters of some phosphorus acids: A laboratory experiment  Glidewell, Christopher; Pogorzelec, Peter J.
Introduces students two reactions in organophosphorus chemistry, the Azbuzov and Atherton-Todd reactions, and involves the use of infrared and 1H and 31P NMR spectra for the identification of the products.
Glidewell, Christopher; Pogorzelec, Peter J. J. Chem. Educ. 1980, 57, 740.
Esters |
Acids / Bases |
IR Spectroscopy |
NMR Spectroscopy
Claisen ester condensation equilibria-model calculations  Garst, John F.
In a Claisen condensation of an ester with but one alpha hydrogen, promoted by a strong base, both reactants and products are deprotonated; because the products are stronger acids than the reactant ester, the net effect is a shift toward products.
Garst, John F. J. Chem. Educ. 1979, 56, 721.
Esters |
Mechanisms of Reactions |
Equilibrium
Excretion of ingested ascorbic acid: An easy, interesting undergraduate experiment  Sirota, G. R.; MacInnis, W. K.; Rasmussen, P. W.
The student ingests ascorbic acid and then measures the amount excreted in his urine using a microfluorometric procedure.
Sirota, G. R.; MacInnis, W. K.; Rasmussen, P. W. J. Chem. Educ. 1979, 56, 421.
Carboxylic Acids |
Vitamins |
Quantitative Analysis
A more convenient method of preparation of amide derivatives of carboxylic acids  Long, Karen P.
An adaptation of this method was devised for use in a qualitative organic analysis program.
Long, Karen P. J. Chem. Educ. 1979, 56, 420.
Synthesis |
Amides |
Carboxylic Acids |
Qualitative Analysis |
Catalysis
Synthesis of some unreported derivatives of sulfonamides: A laboratory in organic chemistry  Gilow, Helmuth
Preparation of N4-benzylsulfanilamide.
Gilow, Helmuth J. Chem. Educ. 1979, 56, 419.
Synthesis |
Amides |
Aromatic Compounds
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
An nmr protonation study of metal diethylenetriaminepentaacetic acid complexes: An integrated senior chemistry experiment  Letkeman, Peter
A protonation study of an aminocarboxylic acid and its metal complexes that can be expanded to cover topics from instrumental techniques to a study of the kinetics of metal-ligand bond formation.
Letkeman, Peter J. Chem. Educ. 1979, 56, 348.
NMR Spectroscopy |
Carboxylic Acids |
Amino Acids |
Coordination Compounds |
Instrumental Methods |
Kinetics |
Crystal Field / Ligand Field Theory
Chemical toxicology. Part I. Organic compounds  Carter, D. E.; Fernando, Quintus
General principles of toxicology, and particular consideration of aliphatics, aromatic, and halogenated hydrocarbons; alcohols, aldehydes, esters, ethers, and ketones; sulfides, mercaptans, and carbon disulfide; nitrogen-containing compounds; and carcinogens.
Carter, D. E.; Fernando, Quintus J. Chem. Educ. 1979, 56, 284.
Toxicology |
Alcohols |
Aldehydes / Ketones |
Esters |
Ethers |
Aromatic Compounds |
Amines / Ammonium Compounds |
Lipids
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
p-Carboxystyrene. A Wittig procedure in aqueous medium  Broos, Rene; Tavernier, Dirk; Anteunis, Marc
In this paper, the authors present a student preparation of p-carboxyl group, as it makes the reaction product soluble in alkaline and insoluble in acid medium, provides for an easy way of separation.
Broos, Rene; Tavernier, Dirk; Anteunis, Marc J. Chem. Educ. 1978, 55, 813.
Aqueous Solution Chemistry |
Acids / Bases |
Carboxylic Acids |
Separation Science
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
Analysis of some synthetic reactions by the HSAB principle  Ho, Tse-Lok
The specificity and efficiency of reactions often have been left unexplained. Addressing these deficiencies, we delineate an empirical analysis of a selected number of synthetic reactions based on the hard and soft acids and bases (HSAB) principle.
Ho, Tse-Lok J. Chem. Educ. 1978, 55, 355.
Acids / Bases |
Synthesis |
Aldehydes / Ketones |
Esters
Favorskii rearrangement in bridged polycyclic compounds  Chenier, Philip J.
Favorskii rearrangement in bridged polycyclic compounds: This can be classified as an intramolecular rearrangement from carbon to carbon, involving a migrating group Z moving without its electrons from migrating origin A to an electron-rich terminus B.
Chenier, Philip J. J. Chem. Educ. 1978, 55, 286.
Mechanisms of Reactions |
Carboxylic Acids |
Aldehydes / Ketones |
Aromatic Compounds
Enzymatic and colorimetric determination of total serum cholesterol. An undergraduate biochemistry laboratory experiment  Taylor, Ronald P.; Broccoli, Anthony V.; Grisham, Charles M.
The authors describe an undergraduate laboratory experiment in which the students determines the level of cholesterol in serum both by colorimetric experiment and by following the procedures of Allain, et al.
Taylor, Ronald P.; Broccoli, Anthony V.; Grisham, Charles M. J. Chem. Educ. 1978, 55, 63.
Enzymes |
Thin Layer Chromatography |
Esters |
Fatty Acids
The oxidation of ethyl lactate  Morgan, E. D.; Goddard, Hilary; Thomas, G. A.
Using pyridinium chlorochromate, ethyl lactate can be oxidized to ethyl pyruvate in a convenient time by carrying out the reaction in refluxing acetone.
Morgan, E. D.; Goddard, Hilary; Thomas, G. A. J. Chem. Educ. 1977, 54, 782.
Oxidation / Reduction |
Catalysis |
Esters
Selective reduction of functionalized carboxylic acids with borane-methyl sulfide: A convenient undergraduate organic experiment  Krishnamurthy, S.; Thompson, Kerry L.
Introduces a new selective reducing agent, borane-methyl sulfide.
Krishnamurthy, S.; Thompson, Kerry L. J. Chem. Educ. 1977, 54, 778.
Carboxylic Acids |
Oxidation / Reduction |
Mechanisms of Reactions
Organic derivatives of oxo acids II. Acids, salts, and esters of Groups IIIA-IVA elements  Fernelius, W. C.; Loening, Kurt; Adams, Roy
Considers the nomenclature of acids, salts, and esters of groups IIIA-VA elements.
Fernelius, W. C.; Loening, Kurt; Adams, Roy J. Chem. Educ. 1977, 54, 509.
Nomenclature / Units / Symbols |
Acids / Bases |
Carboxylic Acids |
Esters
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
Simulation of experimental data, the design of experiments, and the analysis of results. Kinetics of catalyzed ester hydrolysis  Rosenthal, Donald; Arnold, David
A computer program is used in the design, representation, and analysis of experiments.
Rosenthal, Donald; Arnold, David J. Chem. Educ. 1977, 54, 323.
Kinetics |
Esters
Organic derivatives of oxo acids. Part I. Acids, salts, and esters of group VIA elements / Knowledge is ready cash  Fernelius, W. C.; Loening, Kurt; Adams, Roy
Nomenclature of organic derivatives of oxo acids and their salts and esters that are derived from the polybasic acids of the nonmetallic elements of Group IIIA through Group VIA.
Fernelius, W. C.; Loening, Kurt; Adams, Roy J. Chem. Educ. 1977, 54, 299.
Nomenclature / Units / Symbols |
Acids / Bases |
Esters
Isodiazomethane revisited. N-aminoisonitriles  Anselme, J.-P.
The structure, reactions, and preparation of N-aminoisonitriles.
Anselme, J.-P. J. Chem. Educ. 1977, 54, 296.
Reactions |
Mechanisms of Reactions |
Molecular Properties / Structure |
Amides
NMR determination of the rotational barrier in N,N-dimethylacetamide. A physical chemistry experiment  Gasparro, Francis P.; Kolodny, Nancy H.
The barrier to rotation in N,N-dimethylacetamide is determined by measuring changes in nmr line shapes as a function of temperature.
Gasparro, Francis P.; Kolodny, Nancy H. J. Chem. Educ. 1977, 54, 258.
Spectroscopy |
NMR Spectroscopy |
Molecular Properties / Structure |
Amides
CXXX. Background Information on Hexamethylphosphoric Triamide  Steere, Norman V.
Hexamethylphosphoric Triamide has been shown to cause malignant tumors.
Steere, Norman V. J. Chem. Educ. 1976, 53, A12.
Amides |
Toxicology
Reactions of organocopper intermediates. An undergraduate laboratory experiment  Schambach, Robert A.
This paper describes an undergraduate organo-metallic laboratory experiment which investigates the reactivity of organo-copper intermediates generated during the copper-quinoline decarboxylation of o-nitrobenzoic acid.
Schambach, Robert A. J. Chem. Educ. 1976, 53, 735.
Organometallics |
Carboxylic Acids |
Reactions
Structural assignment of a C10H12O3 ester by mass spectroscopy. An undergraduate organic problem  Marchand, Alan P.; Jackson, Danny
The authors provide challenging problems to help students integrate spectroscopic methods.
Marchand, Alan P.; Jackson, Danny J. Chem. Educ. 1976, 53, 390.
Spectroscopy |
Synthesis |
Esters |
Mass Spectrometry
The determination of a mechanism of isomerization of maleic acid to fumaric acid  Meek, John S.
Procedure in which students attempt to determine the mechanism for the isomerization of maleic acid to fumaric acid by heating with hydrochloric acid.
Meek, John S. J. Chem. Educ. 1975, 52, 541.
Mechanisms of Reactions |
Molecular Properties / Structure |
Stereochemistry |
Carboxylic Acids
Benzylthiuronium bicarbonate for the derivatization of carboxylic acids  Reddy, J. V. Krishna; Bopari, K. S.
Preparing benzylithiuronium carboxylates with benzylithiuronium bicarbonate.
Reddy, J. V. Krishna; Bopari, K. S. J. Chem. Educ. 1975, 52, 324.
Carboxylic Acids |
Synthesis
Spatter shield  Wander, J. D.
A method for reducing spatter in the conversion of aniline to sulfanilamide.
Wander, J. D. J. Chem. Educ. 1975, 52, 127.
Laboratory Equipment / Apparatus |
Amino Acids |
Amides
The ethylene ketal protecting group in organic synthesis. An undergraduate laboratory experiment  Paulson, D. R.; Hartwig, A. L.; Moran, G. F.
This reactive sequence involves the preparation of the ethylene ketal of ethyl acetoacetate using the standard p-toluene-sulfonic acid catalyzed procedure; once the reactive ketone moiety has been masked, the reactive ester group can be modified.
Paulson, D. R.; Hartwig, A. L.; Moran, G. F. J. Chem. Educ. 1973, 50, 216.
Synthesis |
Esters |
Aldehydes / Ketones
The chemistry of nitrosoamides  Lobl, Thomas J.
Reviews the photochemistry, base and acid catalyzed decompositions, and thermal decompositions of the nitrosoamides.
Lobl, Thomas J. J. Chem. Educ. 1972, 49, 730.
Amides |
Photochemistry |
Catalysis |
Reactions
Probing chemical reactivity with the diphenyldiazomethane reaction  Dack, Michael R. J.
Examines uses of the reaction between diphenyldiazomethane and carboxylic acids to study the effects of temperature, pressure, solvent, and other variables.
Dack, Michael R. J. J. Chem. Educ. 1972, 49, 600.
Reactions |
Rate Law |
Kinetics |
Carboxylic Acids
The origin of the inductive effect  Stock, Leon M.
The results obtained in the investigation of the dissociation constants of carboxylic acids of known geometry and free from the complicating features of pi electron interactions and steric effects have established that the magnitude of the polar effect does not depend on either the number or the nature of the atoms between the substituent and the reaction site, nor do such substituent contributions depend on the number of paths available for their propagation.
Stock, Leon M. J. Chem. Educ. 1972, 49, 400.
Molecular Properties / Structure |
Carboxylic Acids
The hydrolysis of 4-nitrophenol phosphate. A freshman class investigation  Hopkins, Harry P., Jr.; Mather, Jane H.
A study of the hydrolysis of 4-nitrophenol phosphate is made the basis of a biochemistry-oriented quarter in freshman chemistry; after completing the simple hydrolysis studies, the student proceeds to investigate the enzymatic hydrolysis of 4-nitrophenol phosphate.
Hopkins, Harry P., Jr.; Mather, Jane H. J. Chem. Educ. 1972, 49, 126.
Reactions |
pH |
Esters |
Enzymes |
Catalysis
Fragmentation mechanisms in mass spectrometry  Campbell, M. M.; Runquist, O.
Presents a precise mechanistic notation that is useful in teaching fragmentation processes.
Campbell, M. M.; Runquist, O. J. Chem. Educ. 1972, 49, 104.
Mass Spectrometry |
Alkenes |
Aromatic Compounds |
Alcohols |
Ethers |
Amines / Ammonium Compounds |
Aldehydes / Ketones |
Esters |
Amides
Actual effects controlling the acidity of carboxylic acids  Calder, G. V.; Barton, T. J.
The authors discuss the inaccurate treatment of the actual effects controlling the acidity of carboxylic acids found in many textbooks.
Calder, G. V.; Barton, T. J. J. Chem. Educ. 1971, 48, 338.
Acids / Bases |
Carboxylic Acids |
Reactions
Measurement of acidic catalysis. A physical-organic laboratory experiment  Berndt, Donald C.
This article describes an experiment for undergraduate laboratory courses which illustrate the acidic catalysis of many reactions of carbonyl and carboxyl functions.
Berndt, Donald C. J. Chem. Educ. 1971, 48, 200.
Carboxylic Acids |
Acids / Bases |
Reactions
Benzoic acid tree  Chen, Philip S.
Benzaldehyde undergoes autoxidation to benzoic acid by air, particularly upon exposure to light; the white benzoic acid is caused to form a crystalline tree on twisted pipe cleaners.
Chen, Philip S. J. Chem. Educ. 1970, 47, A119.
Carboxylic Acids |
Acids / Bases |
Crystals / Crystallography |
Oxidation / Reduction |
Aldehydes / Ketones
Detection of carboxylic acids by formation of ferric hydroxamates  Cleland, George H.; Knight, Duane W.
Offers an improved method for the detection of carboxylic acids through the formation of ferric hydroxamates.
Cleland, George H.; Knight, Duane W. J. Chem. Educ. 1970, 47, 781.
Carboxylic Acids |
Qualitative Analysis
Stereochemistry of the citric acid cycle  Smith, W. Grady; York, J. Lyndal
A large percentage of biochemistry texts show the trans structure for aconitate but label it cis.
Smith, W. Grady; York, J. Lyndal J. Chem. Educ. 1970, 47, 588.
Stereochemistry |
Molecular Properties / Structure |
Diastereomers |
Carboxylic Acids
The acidities of ascorbic and sialic acids  Hurd, Charies D.
This note concerning the pKa's of ascorbic and sialic acids id presented since the compounds are of general interest to organic chemists and carbohydrate chemists as well as biochemists.
Hurd, Charies D. J. Chem. Educ. 1970, 47, 481.
Acids / Bases |
Vitamins |
Carboxylic Acids |
Molecular Properties / Structure
Linear free energy relationships in the furan and thiophene ring systems  Freeman, Fillmore
The authors have correlated, by multiple linear regression analysis, sets of data taken from the literature with the Hammett equation for the dissociation constants of furoic and thiophene carboxylic acid derivatives.
Freeman, Fillmore J. Chem. Educ. 1970, 47, 140.
Molecular Properties / Structure |
Carboxylic Acids |
Heterocycles
Conversion of sucrose into a carboxylic acid: An undergraduate experiment  Carman, R. M.; Evans, R. F.
A cascade series of experiments transforms cane sugar into a carboxylic acid.
Carman, R. M.; Evans, R. F. J. Chem. Educ. 1969, 46, 847.
Carbohydrates |
Carboxylic Acids |
Heterocycles
Identification of an unknown ester: An analytical-organic experiment  Grob, Robert L.; Husk, G. Ronald
It is the student's challenge to hydrolyze an ester, separate and purify the resultant alcohol and acid, determine several physical and chemical characteristics, and arrive at a logical choice for its identity.
Grob, Robert L.; Husk, G. Ronald J. Chem. Educ. 1969, 46, 769.
Quantitative Analysis |
Esters |
Alcohols |
Carboxylic Acids
Identification of carboxylic acids: Use of N-methylpiperazine and N-phenylpiperazine  Duff, J. G.; Yung, D. K.; Brenner, R. J.; Wilson, B. J.; Racz, W. J.
Demonstrates that N-phenylpiperazine is a useful reagent for the identification of carboxylic acids.
Duff, J. G.; Yung, D. K.; Brenner, R. J.; Wilson, B. J.; Racz, W. J. J. Chem. Educ. 1969, 46, 388.
Carboxylic Acids |
Qualitative Analysis
Kinetics of condensation polymerization: Preparation of a polyester  McCaffery, Edward L.
This experiment involves determining the reaction-rate constant for a condensation polymerization.
McCaffery, Edward L. J. Chem. Educ. 1969, 46, 59.
Kinetics |
Polymerization |
Synthesis |
Esters |
Rate Law
The Hofmann amide rearrangement  Schreck, James O.
N-bromobenzamide and phenyl isocyanate are subjected to the same conditions required to convert benzamide to aniline to demonstrate that the former two compounds could be intermediates in the Hofmann rearrangements of benzamide.
Schreck, James O. J. Chem. Educ. 1968, 45, 670.
Amides |
Synthesis |
Mechanisms of Reactions
The dissociation of acetic acid dimer in the gas phase  Barton, Donald; Ralph, Roy; Kane, Kevin
The dissociation of acetic acid dimer in the gas phase is used to determine the temperature dependence of equilibrium constants.
Barton, Donald; Ralph, Roy; Kane, Kevin J. Chem. Educ. 1968, 45, 440.
Acids / Bases |
Gases |
Equilibrium |
Carboxylic Acids
The methanolysis of substituted methyl benzoates: An exchange reaction illustrating linear free energy relationships  Glover, I. T.; Peterson, C. W.
Exchange of the carbon-14 labeled methoxyl group in substituted methyl benzoates with nonlabeled methanol provides a laboratory experiment illustrating radioisotope applications, exchange reaction kinetics, and linear free energy relationships for correlation of substituent effects on reaction rates.
Glover, I. T.; Peterson, C. W. J. Chem. Educ. 1968, 45, 241.
Esters |
Kinetics |
Isotopes |
Rate Law
The identification of vegetable oils: A gas chromatographic experiment  Cover, Richard E.
In this procedure the student is given a sample of oil which he saponifies and then esterfies to form the methyl esters of the fatty acids; the esters are then extracted, concentrated, and identified through gas chromatography.
Cover, Richard E. J. Chem. Educ. 1968, 45, 120.
Gas Chromatography |
Instrumental Methods |
Esters |
Qualitative Analysis
Hydrolysis of monosubstituted orthophosphate esters  Bunton, C. A.
Examines the mechanism of the hydrolyses of mono-alkyl and -aryl derivatives of orthophosphoric acid.
Bunton, C. A. J. Chem. Educ. 1968, 45, 21.
Esters |
Mechanisms of Reactions |
Nucleophilic Substitution
Improved polymer tubes  Maycock, W. E.; Hoelzel, C. B.
Suggests improvements to the polymer tubes and procedures used in the small-scale preparation of polyesters.
Maycock, W. E.; Hoelzel, C. B. J. Chem. Educ. 1967, 44, 716.
Esters |
Polymerization
Recyclization apparatus for esterification  Naff, M. Benton; Naff, Anna S.
Describes an apparatus and procedure involved in preparing and distilling n-butyl acetate.
Naff, M. Benton; Naff, Anna S. J. Chem. Educ. 1967, 44, 680.
Laboratory Equipment / Apparatus |
Esters
Kinetic study by NMR  Socrates, G.
This experiment uses NMR to examine the kinetics of the hydration of pyruvic acid.
Socrates, G. J. Chem. Educ. 1967, 44, 575.
NMR Spectroscopy |
Kinetics |
Carboxylic Acids |
Alcohols
Preparation and crosslinking of an unsaturated polyester: An organic chemistry experiment  Stevens, M. P.
Unsaturated polyesters are ideally suited for introducing students to polymer chemistry in the laboratory because they are easy to prepare, the use both condensation and addition polymerization, and they serve to demonstrate the techniques involved in preparing the most widely used polymers.
Stevens, M. P. J. Chem. Educ. 1967, 44, 160.
Polymerization |
Esters
alpha-Chymotrypsin: Enzyme concentration and kinetics  Bender, Myron L.; Kezdy, Ferenc J.; Wedler, Fred C.
Spectrophotometric methods are used to explore the kinetics of ester hydrolysis by alpha-chymotrypsin.
Bender, Myron L.; Kezdy, Ferenc J.; Wedler, Fred C. J. Chem. Educ. 1967, 44, 84.
Enzymes |
Kinetics |
Proteins / Peptides |
Esters
Enamine reactions for the undergraduate organic laboratory: A student water separator  Darling, S. D.
This note describes the design and efficiency of a device that facilitates the removal of water in reactions such as enamine preparation or esterfications.
Darling, S. D. J. Chem. Educ. 1966, 43, 665.
Laboratory Equipment / Apparatus |
Amines / Ammonium Compounds |
Esters |
Synthesis |
Separation Science
Intermolecular association and molar polarization: Physical chemistry experiment  Schrier, Eugene E.
In the experiment describes, the concentration dependence of the molar polarization of a solute is obtained for the amides 2-oxohexamethyleneimine (caprolactam) and N-methylacetamide in benzene solution.
Schrier, Eugene E. J. Chem. Educ. 1966, 43, 257.
Amides
The direct esterification of phenols  Offenhauer, Robert D.
It is not true that phenols cannot be esterfied by the direct action of an organic acid; includes an experiment demonstrating the fallacy of this common textbook error.
Offenhauer, Robert D. J. Chem. Educ. 1964, 41, 39.
Phenols |
Esters |
Reactions
Determination of saponification equivalents of phenolic esters  Tobey, S. W.
Suggests several questions for exploration regarding the determination of saponification equivalents of phenolic esters.
Tobey, S. W. J. Chem. Educ. 1963, 40, A986.
Esters |
Phenols
Esterification for the introductory organic laboratory course: A modified Dean-Stark trap  Puterbaugh, W. H.; Vanselow, C. H.; Nelson, K.; Shrawder, E. J.
Describes a simplified construction for a Dean-Stark trap and its use to determine optimum conditions for the preparation of n-amul acetate.
Puterbaugh, W. H.; Vanselow, C. H.; Nelson, K.; Shrawder, E. J. J. Chem. Educ. 1963, 40, 349.
Esters |
Synthesis
Random and systematic errors in the determination of association constants  Pasternak, R. A.; Brady, A. P.
Examines random and systematic errors in the context of studying association equilibria in solution of carboxylic acids and amides.
Pasternak, R. A.; Brady, A. P. J. Chem. Educ. 1963, 40, 254.
Equilibrium |
Chemometrics |
Carboxylic Acids |
Amides
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
Infrared spectra of silver salts to characterize carboxylic acids  Bonner, William A.; DeGraw, Joseph I., Jr.
Describes the use of infrared spectra of silver salts to characterize carboxylic acids.
Bonner, William A.; DeGraw, Joseph I., Jr. J. Chem. Educ. 1962, 39, 639.
Qualitative Analysis |
Carboxylic Acids |
IR Spectroscopy
Determination of saponification equivalents of phenolic esters  Tobey, Stephen W.; McGregor, S. D.; Cottrill, Sharon L.
The objective of this paper is to show that by making a few key changes in existing techniques, a procedure of saponification determination is evolved that is not only applicable to ordinary alkyl esters of carboxylic acids, but gives excellent results with a wide variety of esters of phenol and other aromatic hydroxyl compounds.
Tobey, Stephen W.; McGregor, S. D.; Cottrill, Sharon L. J. Chem. Educ. 1961, 38, 611.
Esters |
Carboxylic Acids |
Phenols |
Aromatic Compounds
Toxic phosphorus esters (O'Brien, Richard D.)  Treece, Robert E.

Treece, Robert E. J. Chem. Educ. 1961, 38, 380.
Toxicology |
Esters
A group experiment on the Hammett sigma-rho relation  Leisten, J. A.
The second-order alkaline hydolysis of an ester is used to illustrate the Hammett sigma-rho relation.
Leisten, J. A. J. Chem. Educ. 1961, 38, 302.
Kinetics |
Esters
Some aspects of anti-acetyl-cholinesterase chemistry  Rubin, Robert T.
Examines several types of anti-acetylcholinesterase compounds and their practical applications.
Rubin, Robert T. J. Chem. Educ. 1959, 36, 306.
Enzymes |
Kinetics |
Mechanisms of Reactions |
Esters
Reactions in liquid ammonia  Watt, George W.
This article considers five classes of reaction in liquid ammonia: reaction in which participation of the solvent is either absent or incidental, ammoniation, ammonolysis, reactions of alkali and alkaline earth metal amides, and reactions of solutions of metals.
Watt, George W. J. Chem. Educ. 1957, 34, 538.
Reactions |
Metals |
Amides |
Amines / Ammonium Compounds
Hydrogen bonding and physical properties of substances  Ferguson, Lloyd N.
Physical properties influenced by hydrogen bonding considered in this paper include transition temperatures, vapor pressure, water solubility, the ionization of carboxylic acids, stereoisomerism, adsorption, and infrared spectra.
Ferguson, Lloyd N. J. Chem. Educ. 1956, 33, 267.
Hydrogen Bonding |
Noncovalent Interactions |
Physical Properties |
Aqueous Solution Chemistry |
Carboxylic Acids |
Stereochemistry |
IR Spectroscopy
Thioacetamide as a source of hydrogen sulfide in qualitative analysis  Lehrman, Leo
Examines the advantages and disadvantages of using a water solution of thioacetamide as a source of hydrogen sulfide to precipitate metal sulfides in qualitative analysis.
Lehrman, Leo J. Chem. Educ. 1955, 32, 474.
Amides |
Qualitative Analysis
A mnemonic for dicarboxylic acids  Cox, Gerald J.
This short note provides a mnemonic for the names of the dicarboxylic acids.
Cox, Gerald J. J. Chem. Educ. 1955, 32, 363.
Acids / Bases |
Nomenclature / Units / Symbols |
Carboxylic Acids
Editor's outlook  Rakestraw, Norris W.
Unless the prospects of a scientific career include the spirit of freedom, we are unlikely to attract to it the kind of young men and women who in the long run will pursue it most effectively and productively.
Rakestraw, Norris W. J. Chem. Educ. 1955, 32, 343.
Student / Career Counseling |
Aromatic Compounds |
Amides
The identification of esters of phenols  Carbone, Gabriel
The present modification is designed to better characterize esters of phenols and is based on the observations that the potassium salts of phenols are soluble in absolute alcohol wile the potassium salts of organic acids are relatively insoluble in absolute methanol.
Carbone, Gabriel J. Chem. Educ. 1953, 30, 315.
Phenols |
Esters |
Qualitative Analysis