KINETICS AND MECHANISM OF AMMONOLYSIS AND ALKALINE-HYDROLYSIS OF NAPHTHYL ACETATES IN AQUEOUS-MEDIUM - PART 1 - 4-SUBSTITUTED 1-NAPHTHYL ACETATES

A series of 4-substituted 1-naphthyl acetates have been prepared. The kinetics of their ammonolysis have been followed at 20 degrees, 25 deg rees and 30 degrees C under pseudo-first order conditions at different pH in water containing 1% dioxan at an ionic strength of 1.0 mol dm(- 3). The possible mechanisms suggest the existence of general base cata lysis for 4-methyl-1-naphthyl acetate. For esters with electron-withdr awing substituents, ammonolysis proceeds through an unassisted simple nucleophilic substitution pathway. The alkaline hydrolysis of all the esters is also followed under identical reaction conditions.