Chapter 22, Problem 22.11P

Interpretation Introduction

Interpretation: The reason why trichloroacetic anhydride $\left[{\left({\text{Cl}}_{\text{3}}\text{CCO}\right)}_{\text{2}}\text{O}\right]$ is more reactive than acetic anhydride $\left[{\left({\text{CH}}_{\text{3}}\text{CO}\right)}_{\text{2}}\text{O}\right]$ in nucleophilic acyl substitution reactions is to be explained.

Concept introduction: Carboxylic acids and its derivatives undergo nucleophilic acyl substitution. The reaction involves replacement of leaving group $\left(\text{Z}\right)$ by the attacking nucleophile $\left(:{\text{Nu}}^{-}\right)$ or $\text{HNu:}$ (neutral). The reactivity of nucleophilic substitution reaction increases with increase in electron withdrawing group and decreases with increase in number of electron releasing groups.