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The Chemical Educator

ISSN: 1430-4171 (electronic version)

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Abstract Volume 15 (2010) pp 185-186

Dehydration of an Alcohol: An Undergraduate Laboratory Exercise in which Regioisomers give Different Products

Rick C. White* and Benny E. Arney Jr.

Department of Chemistry, Sam Houston State University, Huntsville, TX 77341, Chm_rcw@shsu.edu
Received November 14, 2009. Accepted January 14, 2010.

Published: 25 March 2010

Abstract. This paper describes an undergraduate experiment in which students carry out an acid catalyzed dehydration of one of two regioisomers of an alcohol. These alcohols undergo reaction to give products of either (1) simple dehydration (Saytzeff product) or (2) a mixture of a Hoffmann and rearranged product. The students are required to use NMR spectra to identify the dehydration product(s) and to determine the structure of the starting material based on their dehydration products.

Key Words: Laboratories and Demonstrations; organic chemistry; NMR

(*) Corresponding author. (E-mail: Chm_rcw@shsu.edu)

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