Chapter 27.SE, Problem 16MP

Interpretation Introduction

Interpretation:

A mechanism involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid is to be proposed.

Concept introduction:

The steps involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid are i) Protonation of the hydroxyl group by sulfuric acid ii) Loss of water to yield a carbocation iii) Migration of a ring carbon to produce a more stable carbocation. iv) Deprotonation.

To propose:

A mechanism involving a carbocation rearrangement for the conversion of isoborneol into camphene on treatment with dilute sulfuric acid.