Abstract
The simultaneous neutral and acid-catalysed hydrolyses of different chloro-substituted alkyl acetates in water and in aqueous acetone solutions have been studied using electrolyte solutions of constant ionic strength. The mechanism of the acid-catalysed hydrolyses of monochloroesters is AAC2. When an ester has two chloro-substituents the acid-catalysed hydrolysis takes place simultaneously by the AAC2 and A–BAC3 mechanisms and in the case of trihalogenated esters the mechanism is A–BAC3, a mechanism with an unsymmetrically catalysed partition of the intermediate formed from the water-catalysed addition of water to the carbonyl group of the ester. Structural and solvent effects of these reactions are discussed.
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