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ERIC Number: EJ820289
Record Type: Journal
Publication Date: 2006-Jul
Pages: 3
Abstractor: As Provided
ISSN: ISSN-0021-9584
Rapid and Stereoselective Conversion of a "trans"-Cinnamic Acid to a beta-Bromostyrene
Evans, Thomas A.
Journal of Chemical Education, v83 n7 p1062-1064 Jul 2006
The stereoselective synthesis of an aryl vinyl bromide is accomplished in a rapid microscale reaction of "trans"-4-methoxycinnamic acid with N-bromosuccinimide in dichloromethane. The product is purified by dry column vacuum chromatography and its stereochemistry is determined by [superscript 1]H NMR. TLC, GC and GC-MSD can also be used. This guided-inquiry experiment links reactivity, stereochemistry, and mechanism in electrophilic addition reactions of alkenes and in E1 and E2 elimination reactions that form alkenes. (Contains 3 schemes and 1 figure.)
Division of Chemical Education of the American Chemical Society. Subscription Department, P.O. Box 1267, Bellmawr, NJ 08099-1267. Tel: 800-691-9846; Tel: 856-931-5825; Fax: 856-931-4115; e-mail:; Web site:
Publication Type: Journal Articles; Reports - Descriptive
Education Level: Higher Education; Postsecondary Education
Audience: N/A
Language: English
Sponsor: N/A
Authoring Institution: N/A