Mechanisms of nucleophilic substitution. Kinetics of the reactions of benzyl and diphenylmethyl chlorides in aqueous acetone

Abstract

The unified mechanism of nucleophilic substitution cannot account for the present observations on the rates of decomposition of benzyl and diphenylmethyl chlorides in aqueous acetone; this also applies to any extension of the unified mechanism which does not include carbonium ions as intermediates (mechanism S_N1) and a separate reaction path involving direct nucleophilic attack on the substrate (mechanism S_N2).