Chapter 6.6, Problem 10P

Interpretation Introduction

Interpretation:

An explanation for the very large spread in reaction rates of solvolysis, in case of open chain tertiary alkyl halide and two bicyclic bridgehead alkyl halides is to be given.

Concept Introduction:

Solvolysis is a nucleophilic substitution reaction in which the solvent itself acts as a nucleophile.

${\text{S}}_{\text{N}}\text{1}$ reactions proceed with the formation of a carbocation in the first step.

A bridgehead carbocation is unstable because the ring structure puts a restriction on its ability to assume the normal planar configuration.