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Journal Articles: 25 results
Synthesis of Methyl Diantilis, a Commercially Important Fragrance  William H. Miles and Katelyn B. Connell
Describes the synthesis of a family of fragrances, including the commercially important Methyl Diantilis, and provides an excellent introduction to intellectual property laws.
Miles, William H.; Connell, Katelyn B. J. Chem. Educ. 2006, 83, 285.
Alcohols |
Food Science |
Catalysis |
Ethers |
Industrial Chemistry |
IR Spectroscopy |
Lewis Acids / Bases |
NMR Spectroscopy |
Oxidation / Reduction |
Synthesis
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
A Microwave-Assisted Reduction of Cyclohexanone Using Solid-State-Supported Sodium Borohydride  Lori L. White and Kevin W. Kittredge
We report a microwave-assisted reduction of cyclohexanone by sodium borohydride that is supported on SiO2. The reaction was completed in less than 3 minutes. Workup and analysis by GCMS, IR, and 1H NMR was possible in a two and half-hour laboratory session. This reduction was used successfully in a second-year organic chemistry laboratory. Students were exposed to a green chemistry reaction using solid-state-supported reactants in the absence of solvent.
White, Lori L.; Kittredge, Kevin W. J. Chem. Educ. 2005, 82, 1055.
Oxidation / Reduction |
Solid State Chemistry |
Green Chemistry |
Alcohols |
Aldehydes / Ketones
Ethanol Metabolism and the Transition from Organic Chemistry to Biochemistry  Richard D. Feinman
Introducing alcohol dehydrogenase and aldehyde dehydrogenase reactions in organic chemistry to ease transition to biochemistry.
Feinman, Richard D. J. Chem. Educ. 2001, 78, 1215.
Metabolism |
Oxidation / Reduction |
Reactions |
Mechanisms of Reactions |
Alcohols |
Carbohydrates
Organic-Solvent-Free Phase-Transfer Oxidation of Alcohols Using Hydrogen Peroxide  Martin Hulce and David W. Marks
Six representative alcohols are oxidized to the corresponding aldehyde or ketone, integrating the various techniques of extraction, drying, filtration, column chromatography, gas chromatography, NMR and IR spectroscopy, and reaction kinetics.
Hulce, Martin; Marks, David W. J. Chem. Educ. 2001, 78, 66.
Catalysis |
Oxidation / Reduction |
Reactions |
Kinetics |
Chromatography |
Gas Chromatography |
Separation Science |
NMR Spectroscopy |
IR Spectroscopy |
Alcohols |
Phenols
A Microscale Oxidation Puzzle  Michael W. Pelter, Rebecca M. Macudzinski, and Mary Ellen Passarelli
We have adapted oxidation of an alcohol with sodium hypochlorite solution to a "puzzle" approach by using a diol as the substrate for oxidation. The diols under investigation have both a primary and a secondary hydroxyl group. The assignment is to perform the reaction and determine the structure of the product through interpretation of the IR spectrum.
Pelter, Michael W.; Macudzinski, Rebecca M.; Passarelli, Mary Ellen. J. Chem. Educ. 2000, 77, 1481.
IR Spectroscopy |
Microscale Lab |
Alcohols |
Oxidation / Reduction |
Molecular Properties / Structure
Kinetic Isotope Effect in the Chromic Acid Oxidation of Secondary Alcohols  Charles E. Harding, Christopher W. Mitchell, and Jozsef Devenyi
The kinetic isotope effect is an invaluable tool in studying certain organic reaction mechanisms. Two activities involving the technique that are suitable for introductory organic laboratory students are described. A simple competition experiment utilizing the benzhydrol?benzhydrol-d1 system and chromic acid oxidation is used to demonstrate qualitatively that there is a kinetic isotope effect involved in this process.
Harding, Charles E.; Mitchell, Christopher W.; Devenyi, Jozsef. J. Chem. Educ. 2000, 77, 1042.
Isotopes |
Kinetics |
Mechanisms of Reactions |
Alcohols |
Oxidation / Reduction
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
The Discovery-Oriented Approach to Organic Chemistry 2. Selectivity in Alcohol Oxidation: An Exercise in 1H NMR Spectroscopy for Sophomore Organic Laboratories  Steven R. Shadwick and Ram S. Mohan
A simple oxidation experiment that presents the student with a puzzle and is a good exercise in 1H NMR spectroscopy. The experiment, which illustrates the important concept of selectivity in organic synthesis, involves selective oxidation of a mixture of 1-heptanol and 2-heptanol using commercial swimming pool chlorine.
Shadwick, Steven R.; Mohan, Ram S. J. Chem. Educ. 1999, 76, 1121.
NMR Spectroscopy |
Alcohols |
Oxidation / Reduction |
Synthesis
The Chemical Adventures of Sherlock Holmes: The Baker Street Burning  Thomas G. Waddell and Thomas R. Rybolt
A chemical mystery featuring Sherlock Holmes and Dr. Watson.
Thomas G. Waddell and Thomas R. Rybolt. J. Chem. Educ. 1998, 75, 484.
Enrichment / Review Materials |
Forensic Chemistry |
Qualitative Analysis |
Oxidation / Reduction |
Alcohols |
Dyes / Pigments
Phase Transfer Catalysis Applied to Oxidation  Claude Amsterdamsky
Benzhydrol and cycloheptanol have been oxidized to ketones using commercial bleach as oxidizer and tetrabutylammonium hydrogen sulfate as a phase transfer catalyst.
Amsterdamsky, Claude. J. Chem. Educ. 1996, 73, 92.
Alcohols |
Oxidation / Reduction |
Aldehydes / Ketones |
Catalysis
A mild and convenient oxidation of alcohols: Benzoin to benzil and borneol to camphor  Straub, Thomas S.
A traditional organic chemistry laboratory poses threat to both student safety and the environment: this author provides an alternative procedure.
Straub, Thomas S. J. Chem. Educ. 1991, 68, 1048.
Heterocycles |
Oxidation / Reduction |
Alcohols
Hydroboration-oxidation of (1R)-(+)-alpha-pinene to isopinocampheol: A microscale experiment that displays regio- and stereochemistry using NMR spectroscopy and molecular mechanics calculations  Blankespoor, Ronald L.; Piers, Kenneth
The hydroboration-oxidation of alkenes is an important route to alcohols and therefore receives considerable treatment in standard organic textbooks. These authors present their findings of an example (an alkene that undergoes the hydroboration oxidation process) that displays both regiochemistry and stereochemistry.
Blankespoor, Ronald L.; Piers, Kenneth J. Chem. Educ. 1991, 68, 693.
Alkenes |
Oxidation / Reduction |
NMR Spectroscopy |
Alcohols
Hydroboration for the large organic laboratory  Pickering, Miles
This paper reports an experiment in hydroboration without large hood space requirements, without special glassware requirements, and without inert atmospheric precautions.
Pickering, Miles J. Chem. Educ. 1990, 67, 436.
Oxidation / Reduction |
Alkenes |
Alcohols |
Qualitative Analysis
Oxidation of cyclohexanol - An amoebalike reaction  Kolb, Kenneth E.; Kolb, Doris
Cyclohexanol is oxidized to cyclohexanone.
Kolb, Kenneth E.; Kolb, Doris J. Chem. Educ. 1989, 66, 955.
Oxidation / Reduction |
Alcohols |
Reactions
Comparison of chemical oxidation of alkanes, alkenes, and alcohols on the overhead projector  Kolb, Kenneth E.
This overhead projector demonstration utilizes two classical oxidants, permanganates and dichromate, to distinguish between alkanes, alkenes, and primary, secondary, and tertiary alcohols.
Kolb, Kenneth E. J. Chem. Educ. 1986, 63, 977.
Alcohols |
Alkanes / Cycloalkanes |
Alkenes |
Oxidation / Reduction |
Qualitative Analysis
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
The design of laboratory experiments in the 1980's: A case study on the oxidation of alcohols with household bleach  Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G.
Improved safety by replacing chromium(VI) with bleach in the oxidation of an alcohol.
Mohrig, Jerry R.; Nienhuis, David M.; Linck, Catherine F.; Van Zoeren, Carol; Fox, Brian G.; Mahaffy, Peter G. J. Chem. Educ. 1985, 62, 519.
Oxidation / Reduction |
Alcohols |
Mechanisms of Reactions
Oxidation of alcohols using calcium hypochlorite and solid/liquid phase-transfer catalysis  Hill, John W.; Jenson, Jeffrey A.; Henke, Charles F.; Yaritz, Joseph G.; Pedersen, Richard L.
Includes synthesis of an aldehyde from a primary alcohol as well as several ketones from secondary alcohols.
Hill, John W.; Jenson, Jeffrey A.; Henke, Charles F.; Yaritz, Joseph G.; Pedersen, Richard L. J. Chem. Educ. 1984, 61, 1118.
Alcohols |
Oxidation / Reduction |
Catalysis |
Aldehydes / Ketones |
Synthesis
A phase transfer catalyzed permanganate oxidation: preparation of vanillin from isoeugenol acetate  Lampman, Gary M.; Sharpe, Steven D.
There are several attractive features in this reaction sequence for the undergraduate laboratory. These include (1) use of a protecting acetate group, (2) use of a familiar "textbook" oxidant, potassium permanganate, (3) use of phase transfer catalyst, (4) preparing of an aldehyde, (5) short reaction period, and (6) the laboratory has a pleasant aroma.
Lampman, Gary M.; Sharpe, Steven D. J. Chem. Educ. 1983, 60, 503.
Oxidation / Reduction |
Catalysis |
Natural Products |
Synthesis |
Aldehydes / Ketones |
Alcohols |
Aromatic Compounds
Oxidation of cyclohexanol to cyclohexanone by sodium hypochlorite  Zuczek, Norbert M; Furth, Paul S.
A laboratory that was previously published is modified for a smaller scale in this note.
Zuczek, Norbert M; Furth, Paul S. J. Chem. Educ. 1981, 58, 824.
Oxidation / Reduction |
Alcohols |
Aromatic Compounds
Aqueous chromic acid oxidation of secondary alcohols in diethyl ether: A convenient undergraduate organic chemistry experiment  Thompson, Kerry L.; Krishnamurthy, S.; Nylund, Thomas; Ravindranathan, M.
A two-phase procedure for the oxidation of secondary alcohols to ketones that is applicable to a wide variety of substrates.
Thompson, Kerry L.; Krishnamurthy, S.; Nylund, Thomas; Ravindranathan, M. J. Chem. Educ. 1979, 56, 203.
Aqueous Solution Chemistry |
Oxidation / Reduction |
Alcohols |
Ethers |
Synthesis |
Aldehydes / Ketones
Why green? More chemistry in the student synthesis of tris(ethylenediamine) cobalt(III) chloride  Krause, Ronald A.
What began as a "failure" in this laboratory exercise turned into a great opportunity for inquiry.
Krause, Ronald A. J. Chem. Educ. 1978, 55, 453.
Coordination Compounds |
Alcohols |
Equilibrium |
Oxidation / Reduction
Questions [and] Answers  Campbell, J. A.
Six questions requiring an application of basic principles of chemistry. [Debut]
Campbell, J. A. J. Chem. Educ. 1972, 49, 5.
Enrichment / Review Materials |
Vitamins |
Alcohols |
Oxidation / Reduction
Using TLC to follow the oxidation of a secondary alcohol to a ketone  Davis, Michael
A short note regarding a simple procedure involving the use of thin layer chromatography to follow the oxidation of a secondary alcohol to a ketone.
Davis, Michael J. Chem. Educ. 1968, 45, 192.
Chromatography |
Thin Layer Chromatography |
Oxidation / Reduction |
Alcohols |
Aldehydes / Ketones