Mechanistic interpretation of the simultaneous hydrolysis and methanolysis of chloromethyl chloroacetate in weakly acidic aqueous methanol solutions of varying solvent composition

Abstract

The simultaneous hydrolysis and methanolysis of chloromethyl chloroacetate in aqueous methanol at x_w from 1.00 to 0.50 in 0.01 to 0.06 mol dm^–3 perchloric acid solutions have been studied. The methanolysis of the ester in anhydrous and in highly alcohol-rich methanolic hydrogen chloride solutions up to 0.2 mol dm^–3 acid has also been studied. Under the reaction conditions, the neutral B_AC3 reactions are accompanied by the acid-catalysed reactions. The kinetic data are in accord with the conclusion that the acid-catalysed reactions take place simultaneously by the A_AC2 and A–B_AC3 mechanisms, at least at x_w >0.5. The extent to which the A_AC2 mechanism operates with increased methanol content and in methanol the reaction takes place solely by the A_AC2 mechanism.