TIGER

Journal Articles: 76 results
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
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
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
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
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
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
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
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
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 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
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
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
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
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 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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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 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
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
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
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
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
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