Question

Propose a mechanism involving a hydride shift or alkyl shift for each solvolysis reaction. Explain howeach rearrangement forms a more stable intermediate.

(a)

(b)

(c)

(d)

Short answer

(a)

(b)

(c)

(d)

Step-by-step solution

Rearrange product 1

First product is formed by simple SN¹ reaction. Second product is the rearrangement product formed by more stable carbocation.

(a)

Rearrange product 2

(b)

Rearrange product 3

First product is formed by simple SN¹ reaction. Second product is the rearrange product formed by more stable carbocation.

(c)

Rearrange product 4

First product is formed by simple SN¹ reaction. Second product is the rearrange product formed by more stable carbocation.