Chapter 14.SE, Problem 54AP

Interpretation Introduction

Interpretation:

Given that addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as the sole product. Why no other regioisomer is formed is to be explained using resonance structures.

Concept introduction:

In the addition of HCl to alkenes, in the first step, protonation of the double bond by the acid takes place to yield a cation. The cation can react as such or can rearrange to a more stable cation and then react with the chloride ion.

To explain:

Using resonance structures, why addition of HCl to 1-methoxycyclohexene yields 1-chloro-1-methoxycyclohexane as the sole product and no other regioisomer is formed.