Chapter 18, Problem 18.49P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction proceeds dramatically more slowly under the neutral conditions than under either acidic or basic conditions.

Concept introduction:

The rate of a reaction depends on the free energy of activation, which is donated by $\Delta {\text{G}}^{\text{o}}{}^{\text{*}}$. Lesser the energy barrier, lower will be the energy of activation and consequently faster will be the reaction. The electrostatic attraction between the nucleophile and electrophile is weakest under neutral conditions. Under basic conditions, the nucleophile acquires a full negative charge whereas under acidic conditions, the partial positive charge on the carbonyl carbon increases.