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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 16 (2011) pp 6-8

The Synthesis of Isoamyl Acetate (Banana Oil) via an SN2 Reaction

Gary W. Breton

Berry College, Department of Chemistry, PO Box 495016, Mount Berry, GA 30149, gbreton@berry.edu
Received April 9, 2010. Accepted June 17, 2010.

Published: 16 January 2011

Abstract. The S_N2 reaction between 1-bromo-3-methylbutane and sodium acetate trihydrate takes place smoothly and cleanly in hot DMSO. The product is readily identified as isoamyl acetate by analysis of the resulting IR spectrum, as well as by comparison of the observed IR spectrum to readily available reference spectra. Generally, reasonable yields of product (37–93% with an average of 64%) were obtained by students. This laboratory experiment demonstrates the usefulness of the S_N2 reaction in the synthesis of a compound of biological interest (a pheromone of the honey bee) as well as of interest to the food industry (as a banana flavoring agent).

Key Words: Laboratories and Demonstrations; organic chemistry

(*) Corresponding author. (E-mail: gbreton@berry.edu)

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