Chapter 10, Problem 10.12P

Interpretation Introduction

Interpretation:

The complete mechanism for iodination of $\text{2, 6-dimethylcyclohexanone }$ under basic conditions is to be drawn and the major product is to be predicted.

Concept introduction:

Any $\text{α}$ hydrogens present in a carbonyl compound are weakly acidic and can be extracted by a strong base like hydroxide. This converts the electrophilic $\text{α}$ carbon into a strongly nucleophilic species that can be used in a nucleophilic substitution reaction.

As a strong nucleophile, this carbanion favors ${\text{S}}_{\text{N}}\text{2}$ reactions.

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