Chapter 9, Problem 66PP

(a)

Interpretation Introduction

Interpretation:

Explanation should be given for the given alcohols that they cannot be prepared through hydroboration-oxidation reaction.

Concept introduction:

• Hydroboration reaction: In this reaction water molecule is added across the double bond of the alkene in syn pathway. In hydroboration reaction, anti-Markovnikov’s product is favorable which means –OH group attached to less substituted carbon end of the alkene.
• Hydroboration reaction takes place in two steps; first step is syn addition of ${\text{BH}}_{\text{3}}$ and second step is attack of nucleophile (hydroxide ion produced from hydrogen peroxide and ${\text{BH}}_{\text{3}}$).

To give: the explanation for the given alcohol that cannot be prepared through hydroboration-oxidation process.

(b)

Interpretation Introduction

Interpretation:

Explanation should be given for the given alcohols that they cannot be prepared through hydroboration-oxidation reaction.

Concept introduction:

• Hydroboration reaction: In this reaction water molecule is added across the double bond of the alkene in syn pathway. In hydroboration reaction, anti-Markovnikov’s product is favorable which means –OH group attached to less substituted carbon end of the alkene.
• Hydroboration reaction takes place in two steps; first step is syn addition of ${\text{BH}}_{\text{3}}$ and second step is attack of nucleophile (hydroxide ion produced from hydrogen peroxide and ${\text{BH}}_{\text{3}}$).

To give: the explanation for the given alcohol that cannot be prepared through hydroboration-oxidation process.

(c)

Interpretation Introduction

Interpretation:

Explanation should be given for the given alcohols that they cannot be prepared through hydroboration-oxidation reaction.

Concept introduction:

• Hydroboration reaction: In this reaction water molecule is added across the double bond of the alkene in syn pathway. In hydroboration reaction, anti-Markovnikov’s product is favorable which means –OH group attached to less substituted carbon end of the alkene.
• Hydroboration reaction takes place in two steps; first step is syn addition of ${\text{BH}}_{\text{3}}$ and second step is attack of nucleophile (hydroxide ion produced from hydrogen peroxide and ${\text{BH}}_{\text{3}}$).

To give: the explanation for the given alcohol that cannot be prepared through hydroboration-oxidation process.