Chapter 12, Problem 12.46P

Interpretation Introduction

Interpretation:

It is to be explained why the given reaction violates Markovnikov’s rule.

Concept introduction:

The oxymercuration-reduction is the reaction of addition of water across the $\text{C=C}$ bond. The alkene is first reacted with mercury $\left(\text{II}\right)$ acetate, $\text{Hg}{\left(\text{OAc}\right)}_{\text{2}}$, in a water–tetrahydrofuran (THF) solution, and that is followed by reduction with sodium borohydride, ${\text{NaBH}}_{\text{4}}$. The reaction proceeds through formation of a Mercurinium ion intermediate. The electron-withdrawing group at the Mercurinium ion intermediate destabilizes the ion, resulting in the product, following anti-Markovnikov rule.