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The Chemical Educator

ISSN: 1430-4171 (electronic version)

Table of Contents

Abstract Volume 7 Issue 6 (2002) pp 356-358

Syn and Anti Isomer Preference in Oximes: An Undergraduate Organic Chemistry Experiment

Michael D. Mosher* and Scott Meisenbach

Department of Chemistry, University of Nebraska at Kearney, Kearney, NE, 68849-1150, mosherm@unk.edu
Received September 9, 2002. Accepted October 18, 2002

Published online: 1 November 2002

Abstract. An experiment is described that links a nucleophilic carbonyl addition reaction to a study of structure–activity relationships. Students prepare a series of oximes (from readily available ketones and aldehydes) and, with the use of NMR, define the ratio of syn and anti isomers formed in the reaction. From these data, a quantitative assessment of the steric hindrance of hydrogen, methyl, ethyl, isopropyl, and t-butyl can be obtained.

Key Words:  Laboratories and Demonstrations; organic chemistry; synthesis

(*) Corresponding author. (E-mail: mosherm@unk.edu)

Article in PDF format (212 KB) HTML format

Supporting Materials:

A detailed experimental procedure, a student handout, and a sample proton NMR spectrum (with integration) are included in a zip file. (136 KB) 10.1007/s00897020623b

Issue date: December 1, 2002

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