Chapter 21, Problem 21.2YT

Interpretation Introduction

(a)

Interpretation:

The species in the mechanism of Equation $\text{21-4 }$ have to be drawn, and the initial tetrahedral intermediate is to be determined.

Concept introduction:

Aqueous acid chloride is a very acidic solution due to formation of a strong acid and a weak acid. In hydrolysis reaction water participate as reagent and is an elimination reaction. The hydrolysis reaction converts acid chloride group into carboxylic acid and $\text{HCl}$.

$\text{HCl}$ appears as a product in the overall reaction, but it does not appear in the mechanism because the reaction involves water, in which $\text{HCl}$, a strong acid, exists almost entirely as hydronium ion (${\text{H3O}}^{\text{+}}$) and chloride ion (${\text{Cl}}_{\text{2}}$).

Interpretation Introduction

(b)

Interpretation:

How this diagram is consistent with the nucleophilic addition step being the slow step is to be explained.

Concept introduction:

Due to the formation of strong acid and weak acid, aqueous acid chloride is a very acidic solution. In hydrolysis reaction water participate as reagent and is an elimination reaction. The hydrolysis reaction converts acid chloride group into carboxylic acid and $\text{HCl}$.

$\text{HCl}$ appears as a product in the overall reaction, but it does not appear in the mechanism because the reaction involves water, in which $\text{HCl}$, a strong acid, exists almost entirely as hydronium ion (${\text{H3O}}^{\text{+}}$) and chloride ion (${\text{Cl}}_{\text{2}}$).