Kinetics of the base-catalyzed bromination of s -dichloroacetone

Abstract

The kinetics of the bromination of s -dichloroacetone have been studied in aqueous buffer solutions. The reaction is of zero order with respect to bromine and exhibits general catalysis by bases, so that the observed rate is that of the ionization of the ketone. The catalytic effects of four carboxylate anions and of water are closely related to the basic strengths of the catalysts. In relating rates of ionization to the structures of substituted ketones it is neces­sary to correct the observed rates for the degree of hydration of the carbonyl group in aqueous solution. The corrected rates for acetone and its chloro-derivates are discussed in terms of the polar groups which they contain.