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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > November  >
In the Laboratory
The Microscale Laboratory
A Microscale Oxidation Puzzle
Michael W. Pelter, Rebecca M. Macudzinski, and Mary Ellen Passarelli
Department of Chemistry and Physics, Purdue University Calumet, Hammond, IN 46323-2094
Cover
November 2000
Vol. 77 No. 11
p. 1481
Abstract
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. There are three possible outcomes to the reaction: (i) only the primary alcohol is oxidized to the aldehyde (or carboxylic acid); (ii) only the secondary alcohol is oxidized to the ketone; or (iii) both alcohols are oxidized. The assignment is to perform the reaction and determine the structure of the product through interpretation of the IR spectrum. Examples using two commercially available diols are shown.
Supplement
Experimental procedures for the oxidation various compounds are available.
*  Contents JCE2000p1481W.doc (Microsoft Word)
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*  Citation
 Pelter, Michael W.; Macudzinski, Rebecca M.; Passarelli, Mary Ellen. J. Chem. Educ. 2000 77 1481.
*  Keywords
 Inquiry-Based / Discovery Method; IR Spectroscopy; Laboratory Instruction; Microscale; Organic Chemistry; Problem-Based Learning
*  History
 Created:
Last Updated:		 October 6, 2000
August 31, 2005
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