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  Home > JCE Print > Journal of Chemical Education > Issues > 1999  > August  >
In the Laboratory
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
Department of Chemistry, Illinois Wesleyan University, Bloomington, IL 61702
Cover
August 1999
Vol. 76 No. 8
p. 1121
Abstract
We have developed 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. 1H NMR analysis of the product mixture allows the student to determine the selectivity exhibited by the reagent.
Supplement
The supplement materials include NMR spectra of the reactant and product mixtures. The spectra are Adobe Photoshop files, which have been compressed into both sit (for Macintosh) and zip (for Windows) files. They can also be accessed as a pdf file using Acrobat Reader.
*  Contents
*  Download
supp1121.pdf

supp1121.zip

supp1121.sit
More Information
*  Citation
 Shadwick, Steven R.; Mohan, Ram S. J. Chem. Educ. 1999 76 1121.
*  Keywords
 NMR Spectrometry; Organic Chemistry; Problem-Based Learning; Laboratory Instruction
*  History
 Created:
Last Updated:		 July 8, 1999
November 22, 2005
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