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Chapter 17: Q47 (page 898)

Propose a synthetic sequence of this trisubstituted benzene starting from toluene.

Short Answer

Expert verified

Permanganate oxidation is a brutal oxidizing agent where OH and NH2substituents do not survive.

Halogens (X), nitro (-NO2), and SO3H group survive the permanganate oxidation.

Step by step solution

01

Permanganate Oxidation

Permanganate oxidation is a brutal oxidizing agent where OH and NH2substituents do not survive.

Halogens (X), nitro (-NO2), and SO3H group survive the permanganate oxidation.

02

Synthesis of tri-substituted benzene starting from toluene.

The substitution of the chlorine group with toluene is performed by chlorination in the presence of AlCl3.

A carboxylic acid (COOH) group is attached to the benzene ring by oxidizing alkyl benzene. Here, the oxidation of the methyl group forms the carboxylic acid.

The product formed undergoes nitration. The nitration of the given group forms the final product.

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