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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 16 (2011) pp 211-213

A New Look at an Old Reaction: Bromination of trans-Cinnamic Acid

David E. Alonso*,†, Tricia Guadiz, Karl Bernstein, DeeAnne Goodenough-Lashua, and Kathleen Peterson

† Department of Chemistry and Biochemistry, Andrews University, Berrien Springs, MI 49104-0430, alonso@andrews.edu; ‡ Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, IN 46556
Received February 1, 2010. Accepted February 27, 2011.

Published: 20 August 2011

Abstract. The electrophilic addition of molecular bromine to trans-cinnamic acid was significantly improved by conducting the reaction in 2-propanol. The reaction is complete in less than 5 minutes resulting in greater than 95% erythro­2,3-dibromo-3-phenylpropanoic acid. The product was characterized using IR and NMR spectroscopy.

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: alonso@andrews.edu)

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