Chapter 17, Problem 17.77P

Interpretation Introduction

Interpretation:

How the given synthesis would be carried out is to be suggested with necessary reagents.

Concept introduction:

Sodium hydride ($\text{NaH}$) is a strong base but a poor nucleophile. Being a strong base, it deprotonates the alpha carbon in aldehydes and ketone to generate the carbon nucleophile which is the enolate ion. This nucleophile attacks the alkyl group in alkyl halide via ${\text{S}}_{\text{N}}\text{2}$ mechanism to yield alpha-alkylated carbonyl compounds. Sodium borohydride ${\text{(NaBH}}_{\text{4}})$ is a source of a hydride ion (${\text{H}}^{\text{-}}$) that behaves as the reducing agent and reduces ketones $\left({\text{R}}_{\text{2}}\text{ = CO}\right)$ and aldehydes $\left(\text{RCH = O}\right)$ to alcohols $\left(\text{ROH}\right)$.