Chapter 8, Problem 8.47P

Interpretation Introduction

Interpretation:

It is to be explained whether the given intramolecular nucleophilic substitution reaction takes place via ${\text{S}}_{\text{N}}\text{1}$ or ${\text{S}}_{\text{N}}2$ reaction.

Concept introduction:

If the ${\text{S}}_{\text{N}}\text{1}$ reaction occurs at the chiral center, the products formed would be a 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 the carbocation by the 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.

In ${\text{S}}_{\text{N}}2$ reaction, the nucleophile attacks the carbon with the leaving group from the opposite side of the leaving group, which results in the inversion of configuration in the product.