PROBLEM 25.12 - Organic Chemistry

Question

Which amines cannot be prepared by reduction of an amide?

a.

b.

c.

d.

Step-by-Step Solution

Answer

Answer

 The amine a cannot be made by reduction of an amide. 

Condition for the reduction of amide

Amines with a CH₂ or CH₃ bonded to the N can be made by the reduction of an amide. The carbonyl group of amide participates in the reduction and is reduced into the amine.

 

Explanation

a. In the given compound, the nitrogen is bonded to the benzene. Therefore, it cannot be made by reduction of an amide.

 

b. In the given compound, the nitrogen bonded to CH₂ can be made by reduction of an amide.

 

c. In the given compound, the nitrogen bonded to tertiary carbon can be made by reduction of an amide.

 

d. In the given compound, the nitrogen bonded to secondary carbon can be made by reduction of an amide.