PROBLEM 25.25 - Organic Chemistry

Question

Question: Devise a synthesis of each compound from aniline (C₆H₅NH₂₎

a.

b.

Step-by-Step Solution

Answer

Answer

a.

b.

Conversion reaction

• Convert the amine (aniline) into an amide (acetanilide) by the reaction with the acyl chloride.
• Carry out the Friedel–Crafts reaction. 
• Hydrolyze the amide to generate the free amino group. 

Explanation

a. The first step of the reaction involves acylation by the donation of electrons from the amine group. 

 In the second step, the Friedel–Craft alkylation reaction gives the alkyl group on the para position.

 The third step proceeds via the hydrolysis.  

Reaction of aniline to form a.

b.The first step of the reaction involves acylation of the amine group. 

 In the second step, the Friedel–Craft acylation reaction gives the acyl group on the ortho position.  

 The third step proceeds via the hydrolysis.

Reaction of aniline to form b.