Chapter 8, Problem 8.10P

Interpretation Introduction

Interpretation:

For the given reaction, a complete and detailed mechanism is to be drawn assuming that it takes place via ${\text{S}}_{\text{N}}\text{1}$ mechanism. It is to be determined if the reaction will produce a single stereoisomer or it will produce a mixture of stereoisomers. If it produces a mixture, then it is to be determined if the isomers be produced in equal amounts.

Concept introduction:

An ${\text{S}}_{\text{N}}\text{1}$ reaction is a two-step reaction. A carbocation is formed in the first reaction as a result of the leaving group breaking off, taking its bond pair with the carbon atom. The incoming nucleophile attacks the carbocation in the second step, forming the product.

For a substrate molecule containing a chiral center, if the reaction does not occur at the chiral centers and no bonds to the chiral centers are affected in the course of the reaction, then the stereochemical configuration of the substrate and the product remains the same.