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Chapter 25: PROBLEM 25.25 (page 1024)

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

a.

b.

Short Answer

Expert verified

Answer

a.

b.

Step by step solution

01

Conversion reaction

  • Convert the amine (aniline) into an amide (acetanilide) by the reaction with the acyl chloride.
  • Carry out the Friedel鈥揅rafts reaction.
  • Hydrolyze the amide to generate the free amino group.
02

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鈥揅raft 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鈥揅raft acylation reaction gives the acyl group on the ortho position.

The third step proceeds via the hydrolysis.

Reaction of aniline to form b.

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