Chapter 21, Problem 21.41P

Interpretation Introduction

Interpretation:

The hydrolysis of thioester under normal conditions undergo a faster or slower rate than ester is to be explained.

Concept introduction:

The rate of the hydrolysis reaction of ester and amides are mush slow under neutral conditions to be useful for the synthesis. The relative hydrolysis rates of the species are essentially the rate of nucleophilic addition of water to the carbonyl group. The resonance stabilized carbocation decides the rate of the hydrolysis reaction in the rate-determining step. The reactivity of the resonance stabilized structure decides the reactivity of the molecule. If the carbonyl group in the resonance structure is not stabilized, it makes a molecule more reactive and will undergo hydrolysis faster.