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Journal Articles: 27 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 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
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
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
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
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
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
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
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
"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 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
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
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
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
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
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
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
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
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
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
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