Solvent isotope effect on hydrolysis of tertiary butyl chloride

Abstract

Accurate values of the solvent isotope effect for the solvolysis of tertiary butyl chloride as a function of deuterium content and temperature have been obtained by the differential method. The results are not consistent with a simple one-step SN₁ mechanism; however they and the deviations from the Arrhenius equation that the reaction exhibits can be explained by a mechanism involving an intermediate. The nature of the intermediate is discussed.