The hydrolysis of amides, esters, and related compounds in acid solution. Part II. Carbamates

Abstract

The kinetics of the hydrolysis in acid solution of ethyl N-methylcarbamate, ethyl NN-dimethylcarbamate, ethoxycarbonylglycine, ethyl NN-di-isopropylcarbamate, ethyl NN-di-n-propylcarbamate, phenyl carbamate, and phenyl NN-dimethylcarbamate have been studied. Either the A_Ac1 or the A_Ac2 mechanism prevails depending on the acid concentrations. A satisfactory picture of the A_Ac2 reaction is one in which water displaces the protonated alkoxy- or aryloxy-group. The results permit a number of other possible mechanisms to be discarded.