Chapter 20, Problem 85IP

(a)

Interpretation Introduction

Interpretation: The possible side products in the direct conversion of compound 1 to compound 3 have to be identified.

Concept Introduction:

Hydrolysis of alkyl halides:

Using water or hydroxide as nucleophile, alkyl halides can be converted into alcohols. The overall reaction is known as hydrolysis of alkyl halides.

General Scheme:

$\begin{array}{l}\text{R-X}\text{+}\text{NaOH}\stackrel{{\text{H}}_{\text{2}}\text{O/reflux}}{\to }\text{R-OH}\text{+}\text{NaBr}\\ \text{Alkyl}\text{Alcohol}\\ \text{halide}\end{array}$

Hydrolysis of nitriles:

Nitriles on hydrolysis get converted into carboxylic acids.

General scheme:

(b)

Interpretation Introduction

Interpretation: A complete mechanism for the given two step synthesis has to be drawn

Concept Introduction:

$S_{N}2$ reaction:

• It is a bimolecular reaction where breaking and making of bond undergoes in a single step.
• The nucleophile attacks from the backside of electrophilic carbon and forms a bond between carbon and nucleophile. At the same time, the bond between carbon and leaving group breaks.

General mechanism for $S_{N}2$ reaction:

Hydrolysis of ester:

Esters on hydrolysis get converted into carboxylic acids.

General scheme: