TCE     
|
The Chemical Educator
ISSN: 1430-4171 (electronic version)
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/s00897020623bIssue date: December
1, 2002
© The Chemical Educator 1996-2024