Hydrolysis of amides. I. The hydrolysis of acetamide and chloroacetamide in dilute acid

Abstract

Kinetic studies of the hydrolysis of acetamide in dilute acidic solution are reported. These reveal the presence of systematic errors in some previous work on this compound. A consistent treatment is given, leading to values of the energy and entropy of activation (at 75°) of 19.8 kcal and -17.8 e.u. and satisfactory correlation of most previous results. Similar defects are present in recent work on chloroacetamide hydrolysis and the same approach is used in a reinterpretation.