Chapter 12, Problem 12.14P

Interpretation Introduction

Interpretation:

The reagent which can be used for the given transformation is to be determined.

Concept introduction:

The conversion of an alkene to alcohol is carried out by the oxymercuration-reduction reaction. Rearrangement generally does not take place with oxymercuration-reduction because a carbocation intermediate is not formed. The intermediate is a cyclic mercurinium ion.

The product of oxymercuration-reduction follows Markovnikov’s rule. The hydroxyl group (OH) is added to the more substituted carbon atom of the initial double bond. The oxymercuration-reduction carried out with $\text{Hg}{\left(\text{OAc}\right)}_{\text{2}}{\text{, H}}_{\text{2}}\text{O/THF}$ followed by a reduction using ${\text{NaBH}}_{\text{4}}\text{, ethanol}$ respectively.