Chapter 9, Problem 9.66P

Interpretation Introduction

(a)

Interpretation:

The two isomeric products of formula ${\text{C}}_{\text{7}}{\text{H}}_{\text{11}}\text{Br}$ produced by the given reaction are to be drawn.

Concept introduction:

The intermediate of ${\text{S}}_{\text{N}}\text{1}$ reactions is a carbocation. A carbocation is often subject to a rearrangement that produces a more stable carbocation. In this case, each carbocation forms a structurally different product, leading to a mixture of constitutional isomers.

Interpretation Introduction

(b)

Interpretation:

The mechanism that accounts for the formation of each of the two isomeric products is to be drawn.

Concept introduction:

${\text{S}}_{\text{N}}1$ mechanism is a two-step, unimolecular mechanism. The leaving group departs in the first rate-determining step, producing a carbocation. The carbocation may be subject to resonance or a rearrangement if it leads to the formation of a more stable carbocation. The nucleophile can then attack either of the two carbocations in the second step. The product, in this case, is a mixture of constitutional isomers.