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A Microscale Oxidation Puzzle

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Michael W. Pelter , Rebecca M. Macudzinski and Mary Ellen Passarelli

Department of Chemistry and Physics, Purdue University Calumet, Hammond, IN 46323-2094

J. Chem. Educ., 2000, 77 (11), p 1481

DOI: 10.1021/ed077p1481

Publication Date (Web): November 1, 2000

Section:

History, Education, and Documentation

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.

Keywords (Audience):

Second-Year Undergraduate

Keywords (Domain):

Laboratory Instruction

Keywords (Feature):

The Microscale Laboratory

Keywords (Pedagogy):

Inquiry-Based / Discovery Learning

Keywords (Subject):

IR Spectroscopy

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