Chapter 11, Problem 11.30P

Interpretation Introduction

Interpretation:

The complete, detailed mechanism account for the given reaction is to be drawn.

Concept introduction:

The given alkene undergoes an electrophilic addition reaction via carbocation rearrangement. Electrophilic addition of a Bronstead acid across a carbon-carbon double bond is susceptible to carbocation rearrangement. A carbocation rearrangement transforms the less stable carbocation into a more stable carbocation to attend greater stability via $\text{1, 2-hydride shift}$ or $\text{1, 2-methyl shift}$. The carbocation rearrangement is followed by the coordination step to form a neutral product.

The carbocation stabilized by resonace is more stable.