Chapter 8, Problem 8.46P

Interpretation Introduction

Interpretation:

The racemization that occurs when $\left(\text{S}\right)\text{-3, 3-dimethylcyclohexanol}$ is dissolved in dilute acid is to be explained by curved arrow mechanism.

Concept introduction:

When the ${\text{S}}_{\text{N}}\text{1}$ occurs at the chiral center, the products formed would be racemic mixture, i.e., a mixture of both stereochemical configurations. The first step in the ${\text{S}}_{\text{N}}\text{1}$ reaction is the formation of a carbocation by removal of the leaving group. The carbocation is planar; the nucleophile can approach the carbocation from either side and form a mixture of products with both stereochemical configurations.