Kinetics of the reactions of olefins with halogens in aqueous solution. Part III. Reaction of bromine with acrylic acid, crotonic acid, and ethyl acrylate

Abstract

Kinetic measurements are reported for the reaction of aqueous bromine with acrylic and crotonic acids, for both of which the anion is much more reactive than the undissociated molecule. Velocity constants are derived for the reaction of acrylate and crotonate ions with molecular bromine, and of crotonic acid with molecular bromine and tribromide ion, but no contribution could be detected from the reaction of either anion with tribromide ion, or of undissociated acrylic acid with either brominating agent. The ratios of bromohydrin to dibromide in the products of the reaction of bromine with acrylic acid and ethyl acrylate have been measured over a range of bromide ion concentrations. The observed velocity constants and competition factors are discussed in relation to the reaction mechanism.