Chapter 10, Problem 10.11P

Interpretation Introduction

Interpretation:

The complete detailed mechanism for the given reaction is to be drawn.

Concept introduction:

Hydrogen atom(s) present on the $\text{α}$ carbon of an aldehyde or a ketone is acidic and can be extracted by a strong base. This generates a carbanion, a strong nucleophile, which can be used for nucleophilic substitution. Carbocation being a strong nucleophile, favors ${\text{S}}_{\text{N}}\text{2}$ reactions.

In the ${\text{S}}_{\text{N}}\text{2}$ reaction, the nucleophile attacks the electrophilic carbon in the substrate, displacing the leaving group in a single-step, concerted reaction. Since the nucleophile attacks first, it must approach the electrophilic carbon from the direction opposite the leaving group, resulting in a single product with an inverted symmetry at the reaction center.