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  Home > JCE Print > Journal of Chemical Education > Issues > 1995  > July  >
Features
Textbook Forum
Propylene Oxide Addition to Hydrochloric Acid: A Textbook Error
Rebecca E. Phillips and Robert L. Soulen
Southwestern University, Georgetown, TX 78626
Cover
July 1995
Vol. 72 No. 7
p. 624
Abstract
Many current textbooks suggest that, in contrast to base catalyzed epoxide ring opening, acid catalyzed epoxide ring opening reactions proceed via a carbocation intermediate with nucleophilic attack at the more hindered carbon. However, we show that slow addition of propylene oxide to concentrated or dilute hydrochloric acid yields predominantly 1 -chloro-2-propanol and a smaller amount of 2-chloro-1 -propanol. The reaction may be varied by addition of inert solvents or by the addition of sodium bromide to demonstrate changes in the mechanism ( Sn-1 versus Sn-2) and nucleophilic competition.
More Information
*  Citation
 Phillips, Rebecca E.; Soulen, Robert L. J. Chem. Educ. 1995 72 624.
*  Keywords
*  History
 Created:
Last Updated:		 10/1/1999
5/22/2006
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