Question

Question: Which alcohols can be prepared as a single product by hydroboration–oxidation of an alkene? Which alcohols can be prepared as a single product by the acid-catalyzed addition of H₂O to an alkene?

a.

b.

c.

d.

Short answer

Answer

a.Hydroboration–oxidation.

b.Acid-catalyzed addition.

c.Acid-catalyzed addition.

d. Hydroboration–oxidation and acid-catalyzed addition.

Step-by-step solution

Hydroboration-oxidation reaction

Hydroboration–oxidation reaction comes to show the addition of an OH group on the less substituted carbon.

Acid catalyzed addition  

The acid-catalyzed addition of H₂O results in the addition of an OH group on the more substituted carbon.

Explanation

a. The given compound has a substitution of the propyl group. Therefore, the hydroboration- oxidation reaction occurs on the less substituted side.

Hydroboration–oxidation

b. The given compound has a substitution of the methyl group. Therefore, the acid catalyzed reaction occurs on the more substituted side.

Acid-catalyzed addition

c. The given compound has a substitution of the cyclohexyl group. Therefore, the hydroboration reaction occurs on the less substituted side.

Acid-catalyzed addition

d. The given compound has a substitution of the hexyl group. Therefore, the acid catalyzed reaction as well as hydroboration oxidation occurs.

Hydroboration–oxidation and acid-catalyzed addition