Kinetics and mechanism of the hydrolysis of substituted acetophenone oximes in acidic solutions

Abstract

The kinetics of the hydrolysis of acetophenone oxime in moderately concentrated aqueous acids have been studied. Together with an investigation of the approach to the equilibrium between acetophenone oxime and acetophenone in dilute aqueous acid, these studies suggest that the rate-determining step of the hydrolysis in highly acidic media is general base-catalysed loss of hydroxylamine from the cationic tetrahedral intermediate. The effects of substituents on the rate constant for this reaction are reported.