Reactions of β-ketoamides. Part 1. Kinetics of enolisation of acetoacetamide in water and of acetoacetamide and acetoacetanilide in ethanol–water

Abstract

Kinetic results are reported for the rates of enolisation (k_e) of acetoacetamide in water and for acetoacetamide and acetoacetanilide in ethanol–water (70 : 30 v/v) as measured by their rates of halogenation. The effects of nickel (II), zinc(II) and acetate on the rates of enolisation are also described. Unlike β-diketones, the enolisation of β-ketoamides is acid catalysed.

The rates of ketonisation (k_f) of the two β-ketoamides have also been investigated using stopped-flow spectrophotometry. The keto : enol ratios have been derived using the experimentally measured k_e and k_f values.