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  Home > JCE Print > Journal of Chemical Education > Issues > 2006  > July  >
In the Laboratory
The Microscale Laboratory
Rapid and Stereoselective Conversion of a trans-Cinnamic Acid to a β-Bromostyrene
Thomas A. Evans
Department of Chemistry and Biochemistry, Denison University, Granville, OH 43023
Cover
July 2006
Vol. 83 No. 7
p. 1062
Abstract
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 1H 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.
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Instructions for students and notes to instructors are available.
*  Contents Folder JCE2006p1062W containing JCE2006p1062W_1.doc and JCE2006p1062W_2.doc (Microsoft Word)
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*  Citation
 Evans, Thomas A. J. Chem. Educ. 2006 83 1062.
*  Keywords
 Alkenes; Carbocations; Gas Chromatography; Hands-On Learning / Manipulatives; Inquiry-Based / Discovery Learning; Laboratory Instruction; Mechanisms of Reactions; Microscale Lab; NMR Spectroscopy; Organic Chemistry; Second-Year Undergraduate; Stereochemistry
*  History
 Created:
Last Updated:		 5/26/2006
5/31/2006
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