Chapter 12, Problem 12.45P

Interpretation Introduction

(a)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add ${\text{H}}_{\text{2}}\text{O}$ across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (${\text{H}}_{\text{2}}\text{O}$) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.

Interpretation Introduction

(b)

Interpretation:

The mechanism with the organic product(s) for the given reaction is to be drawn.

Concept introduction:

Oxymercuration–reduction is a method to add ${\text{H}}_{\text{2}}\text{O}$ across carbon-carbon double bond or carbon-carbon triple bond.

Oxymercuration-reduction proceeds through a mercurinium ion intermediate and results into addition of water to an alkene or alkyne with Markovnikov regiochemistry. In this reaction, the electron rich double or triple bond attacks the electron poor Hg atom to form mercurinium ion intermediate, which is then attacked by the nucleophile (${\text{H}}_{\text{2}}\text{O}$) to form a three-member ring. The positively charged O atom is deprotonated to form mercuric enol. Subsequent tautomerization converts the mercuric enol into a more stable mercuric keto form, which is hydrolyzed by water to form enol. The enol is then tautomerized to the ketone.