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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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Most popular questions from this chapter

Phenol reacts with three equivalents of bromine in CCl4(in the dark) to give a product of formula C6H3OBr3. When this product is added to bromine water, a yellow solid of molecular formula C6H2OBr4 precipitates out of the solution. The IR spectrum of the yellow precipitate shows a strong absorption (much like that of a quinone) around 1680cm-1 . Propose structures for the two products.

Predict the major products of the following reactions.

(a) toluene + excess CI2 (heat, pressure)

(b) benzamide ( PhCONH2 ) + Na (liquid NH3, CH3 CH2OH)

(c) o-xylene + H2 (1000 psi, 100 °C, Rh catalyst)

(d) p-xylene + Na (liquid NH3, CH3CH2OH )

(e)

What organocuprate reagent would you use for the following substitutions?

A common illicit synthesis of methamphetamine involves an interesting variation of the Birch reduction. A solution of ephedrine in alcohol is added to liquid ammonia, followed by several pieces of lithium metal. The Birch reduction usually reduces the aromatic ring, but in this case, it eliminates the hydroxy group of ephedrine to give methamphetamine. Propose a mechanism, similar to that for the Birch reduction, to explain this unusual course of the reaction

Which reactions will produce the desired product in good yield? You may assume that aluminum chloride is added as a catalyst in each case. For the reactions that will not give a good yield of the desired product, predict the major products.

Reagents Desired Product

(a) benzene + n-butyl bromide n-butylbenzene

(b) ethylbenzene + tert-butyl chloride p-ethyl-tert-butylbenzene

(c) bromobenzene + ethyl chloride p-bromoethylbenzene

(d) benzamide (PhCONH3) + CH3 CH2 CI p-ethylbenzamide

(e) toluene + HNO3, H2SO4 , heat 2,4,6-trinitrotoluene (TNT)
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