Chapter 12, Problem 12.54P

Interpretation Introduction

(a)

Interpretation:

How the given compound can be produced from an alkene using the appropriate deuterated reagents and solvent in a hydroboration-oxidation reaction is to be shown.

Concept introduction:

The hydroboration-oxidation reaction of an alkene is the overall syn addition of the water molecule across the double bond via anti-Markovnikov regiochemistry. The first step of the mechanism is the syn addition of borane across the carbon-carbon double bond. A deuteron from borane is added to the more substituted carbon of the double bond, and the remaining fragment is added to the less substituted carbon to form alkyl borane. The second step is the conversion of the alkyl borane to alkyl borate ester by the action of alkaline ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$. The final step is the hydrolysis of alkyl borate ester by the solvent.

Interpretation Introduction

(b)

Interpretation:

How the given compound can be produced from an alkene using appropriate deuterated reagent and solvent in a hydroboration-oxidation reaction is to be shown.

Concept introduction:

The hydroboration-oxidation reaction of an alkene is the overall syn addition of the water molecule across the double bond via anti-Markovnikov regiochemistry. The first step of the mechanism is the syn addition of ${\text{BH}}_{\text{3}}$ across the carbon-carbon double bond. A proton from ${\text{BH}}_{\text{3}}$ is added to the more substituted carbon of the double bond and the remaining fragment is added to the less substituted carbon to form alkyl borane. The second step is the conversion of the alkyl borane to alkyl borate ester by the action of alkaline ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$. The final step is the hydrolysis of alkyl borate ester by the solvent.

Interpretation Introduction

(c)

Interpretation:

How the given compound can be produced from an alkene using appropriate deuterated reagents and solvent in a hydroboration-oxidation reaction is to be shown.

Concept introduction:

The hydroboration-oxidation reaction of an alkene is the overall syn addition of the water molecule across the double bond via anti-Markovnikov regiochemistry. The first step of the mechanism is the syn addition of borane across the carbon-carbon double bond. A deuteron from borane is added to the more substituted carbon of the double bond and the remaining fragment is added to the less substituted carbon to form alkyl borane. The second step is the conversion of alkyl borane to alkyl borate ester by the action of alkaline ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$. The final step is the hydrolysis of alkyl borate ester by the solvent.