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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > August  >
In the Laboratory
Kinetic Isotope Effect in the Chromic Acid Oxidation of Secondary Alcohols
Charles E. Harding, Christopher W. Mitchell, and Jozsef Devenyi
Department of Chemistry, The University of Tennessee at Martin, Martin, TN 38238

Cover
August 2000
Vol. 77 No. 8
p. 1042

Abstract
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 benzhydrolÐbenzhydrol-d1 system and chromic acid oxidation is used to demonstrate qualitatively that there is a kinetic isotope effect involved in this process. GC-MS operating in the "specific ion monitoring" mode is used for analysis. As a second experiment, a procedure for the quantitative determination of kH/kD in this system is described. The rates of oxidation of the nondeuterated and the deuterated alcohol are followed in separate reactions. Concentrations are determined by GC using an internal standard. Examples of student results for both activities are presented. Both procedures are general and may be used with other alcohols that exhibit strong molecular-ion peaks in their mass spectra. These experiments are ideal for small groups of students and are suited to being performed along with work already being done in the laboratory program.
Supplement
A competition experiment, kinetics experiment, instructor's notes, and equipment needs are included.
*  Contents
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More Information
*  Citation
Harding, Charles E.; Mitchell, Christopher W.; Devenyi, Jozsef. J. Chem. Educ. 2000 77 1042.
*  Keywords
Isotopes; Kinetics; Laboratory Instruction; Mechanisms; Organic Chemistry
*  History
Created:
Last Updated:
July 5, 2000
August 31, 2005
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