TIGER

Journal Articles: 79 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
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
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
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
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
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
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 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
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
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
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
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
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
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
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
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
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 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
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
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
"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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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