Chapter 8, Problem 8.29P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism for the ${\text{S}}_{\text{N}}\text{1}$ reaction between the given reactants is to be drawn.

Concept introduction:

${\text{S}}_{\text{N}}\text{1}$ reaction is the unimolecular nucleophilic substitution reaction. The first step is a slow and it is rate-determining step of the reaction. The carbocation is formed by breaking bond between the carbon atom and leaving group. In the second fast step, the product is formed by reaction between carbocation and nucleophile. If the nucleophile is an uncharged one such as water or alcohol, a final deprotonation step is necessary for the formation of the product.

The carbocation initially produced may rearrange if it produces a more stable carbocation. This will lead to the formation of a mixture of constitutional isomers.