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  Home > JCE Print > Journal of Chemical Education > Issues > 2000  > June  >
In the Laboratory
The Oxidation of Primary Alcohols to Esters: Three Related Investigative Experiments
Chriss E. McDonald
Department of Chemistry, Lycoming College, Williamsport, PA 17701
Cover
June 2000
Vol. 77 No. 6
p. 750
Abstract
Discovery-based experiments are excellent tools for promoting substantive interaction among students and between students and instructors. Three related synthetic puzzles are described. In each case an ester is produced via oxidation of a primary alcohol by calcium hypochlorite and acetic acid. Students are placed in teams of three and a different alcohol is assigned to each member of the group. Each person in the group is responsible for synthesizing, purifying, and spectroscopically analyzing his or her unknown product. As a group, the students are asked to determine the structure of their three nonobvious products and to provide a mechanistic rationale for the transformations.
Supplement
Supplemental materials include student materials (experimental procedures and procedural notes), spectra (MS and NMR), and notes for the instructor.
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*  Citation
 McDonald, Chriss E. J. Chem. Educ. 2000 77 750.
*  Keywords
 Organic Chemistry; Laboratory Instruction; Redox Reactions; Inquiry-Based / Discovery Method
*  History
 Created:
Last Updated:		 April 25, 2000
August 31, 2005
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