Chapter 17, Problem 17.27AP

Interpretation Introduction

(a)

Interpretation:

The structure of compound B that is obtained by the contamination of $3-\text{bromo}-1-\text{butene}$ (A) is to be stated.

Concept introduction:

The chemical reaction in which the double present in the allylic compound migrates to the adjacent carbon atom through nucleophilic substitution reaction is known as allylic rearrangement. Both ${\text{S}}_{\text{N}}\text{1}$ and ${\text{S}}_{\text{N}}2$ reactions can be used for the allylic rearrangement.

Interpretation Introduction

(b)

Interpretation:

A curved-arrow mechanism for the formation of compound B from compound A is to be drawn.

Concept introduction:

The chemical reaction in which the double present in the allylic compound migrates to the adjacent carbon atom through nucleophilic substitution reaction is known as allylic rearrangement. Both ${\text{S}}_{\text{N}}\text{1}$ and ${\text{S}}_{\text{N}}2$ reactions can be used for the allylic rearrangement.

Interpretation Introduction

(c)

Interpretation:

Whether compound A or compound B is the major isomer at equilibrium is to be stated with explanation.

Concept introduction:

The chemical reaction in which the double present in the allylic compound migrates to the adjacent carbon atom through nucleophilic substitution reaction is known as allylic rearrangement. Both ${\text{S}}_{\text{N}}\text{1}$ and ${\text{S}}_{\text{N}}2$ reactions can be used for the allylic rearrangement.