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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–Crafts 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–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.

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Most popular questions from this chapter

Question: What starting materials are needed to prepare each drug using reductive amination? Give all possible pairs of compounds when more than one route is possible.

a.

b.

Alkyl diazonium salts decompose to form carbocations, which go on to form products of substitution, elimination, and (sometimes) rearrangement. Keeping this in mind, draw a stepwise mechanism that forms all of the following products.

How would you separate toluene (C6H5CH3 ), benzoic acid (C6H5CO2H ), and aniline (C6H5NH2 ) by an extraction procedure?

Question: Give a systematic or common name for each compound.

Question: Draw the products of each acid–base reaction. Indicate whether equilibrium favors the reactants or products.

a.

b.

c.
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