Chapter 14.SE, Problem 30AP

Interpretation Introduction

Interpretation:

The possible products resulting from the addition of one equivalent of HCl to 1-phenyl-1,3-butadiene are to be given. Which product predominates is to be stated and the reason for the same also is to be given.

Concept introduction:

Conjugated dienes undergo electrophilic addition reactions through the formation of an allyl carbocation. The allyl cation is resonance stabilized and the attack of bromide ion on each of these forms leads to the formation of a mixture of 1,2- and 1,4-addition products. The more stable allylcation produced will yield the major product.

To give:

The possible products resulting from the addition of one equivalent of HCl to 1-phenyl-1,3-butadiene.

To state:

Which product predominates and to give the reason for the same.