Nucleophilic substitution at trigonal carbon. Part II. Ethanolysis of aliphatic acyl chlorides

Abstract

A bipolar current method for the measurement of rapidly changing resistance has been used to study the rates of solvolysis of a series of aliphatic acyl chlorides in ethanol. Although polar and steric factors are of importance in determining the rate, the substituent effects cannot be satisfactorily correlated by the two-term Taft equation. The results are consistent with a bimolecular reaction, and are best explained by a synchronous displacement mechanism or a combination of this and an addition–elimination mechanism.