Chapter 15, Problem 86P

Interpretation Introduction

Interpretation:

To give the explanation whether the acid-catalyzed hydrolysis of acetamide is a reversible or irreversible reaction.

Concept introduction:

In acid hydrolysis of amide, acid protonates carbonyl oxygen of amide which increases the electrophilicity of the carbonyl carbon. Water acts as a nucleophile gets attached to the carbonyl carbon of amide to form tetrahedral intermediate(A) which on losing proton get converted to tetrahedral intermediate(B). The nitrogen of tetrahedral intermediate (B) gets protonated to form tetrahedral intermediate(C). The ${\text{NH}}_3$ group is eliminated from the tetrahedral intermediate (C) and after that, it gets protonated to form ${\text{NH}}_4{}^{+}$. The mechanism of acid-catalyzed hydrolysis of amides is: