Chapter 11, Problem 46P

Interpretation Introduction

Interpretation:

Whether the acid-catalyzed hydrolysis of acetamide is a reversible or irreversible reaction has to be found and explained.

Concept introduction:

Acid catalyzed reaction: 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: