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.

Question

Reaction of HBr with 3-methylcyclohexene yields a mixture of four products: cis-and trans-1-bromo-3-methylcyclohexane and cis-and trans-1-bromo-2-methylcyclohexane. The analogous reaction of HBr with 3-bromocyclohexene yields trans-1, 2-dibromocyclohexane as the soleproduct. Draw structures of the possible intermediates, and then explain why only a single product is formed in this reaction.

Answer 1

Question

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.

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