Question

Question: What alkene can be used to prepare each alcohol as the exclusive product of a two-step hydroboration–oxidation sequence?

Short answer

Answer

a.

Step-by-step solution

Step 1:Hydroboration-oxidation reaction

The reaction involves the syn addition of $\mathit{B}{\mathit{H}}_{\mathbf{3}}$ to the double bond followed by oxidation to produce R and S alcohols.

Formation of products for a, b and c

a.

The alkene used to produce 2-methylcyclopentanol in the hydroboration-oxidation reaction is shown below:

Alkene in a

b.

The alkenes used to produce 4-methylheptan-3-ol in the hydroboration-oxidation reaction are shown below:

Alkene in b

c.

The alkene used to produce 1-cyclohexylethanol in the hydroboration-oxidation reaction is shown below:

Alkene in c