Chapter 6.7, Problem 11P

Interpretation Introduction

Interpretation:

The two stereoisomeric substitution products formed by the hydrolysis of $\text{cis-1,4-dimethylcyclohexyl bromide}$ and $\text{trans-1,4-dimethylcyclohexyl bromide}$ are to be determined.

Concept introduction:

The nucleophilic substitution reaction of secondary and tertiary alkyl halide proceeds through an ${\text{S}}_{\text{N}}\text{1}$ mechanism.

The ${\text{S}}_{\text{N}}\text{1}$ reaction is the unimolecular nucleophilic substitution whose rate determining step involved only one reactant.

The formation of carbocation is the rate determining step in an ${\text{S}}_{\text{N}}\text{1}$ mechanism.

The nucleophile can attacks from either face of planar carbocation in an ${\text{S}}_{\text{N}}1$ mechanism.

There is a chance of formation of a racemic mixture to give a mixture of stereoisomers by the hydrolysis of optically active alkyl halide in an ${\text{S}}_{\text{N}}\text{1}$ mechanism.

The stereoisomers have same connectivity of atoms but the three dimensional spatial arrangement of substituents at a chirality center is different.