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Propylene Oxide Addition to Hydrochloric Acid: A Textbook Error

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Rebecca E. Phillips and Robert L. Soulen

Southwestern University, Georgetown, TX 78626

J. Chem. Educ., 1995, 72 (7), p 624

DOI: 10.1021/ed072p624

Publication Date: July 1995

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.