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NEET
Exam
NEET
Subject
Chemistry
Chapter
Carboxylic Acid Derivatives

NEET · Chemistry · Carboxylic Acid Derivatives

Which of the following statements regarding the oxidation or...

Which of the following statements regarding the oxidation or reduction products of substituted aromatic compounds is incorrect?

Options

  1. AOxidation of pp-nitrotoluene with acidic KMnO4_4 gives an acid stronger than pp-fluorobenzoic acid.
  2. BReduction of pp-nitroanisole with Sn/HCl gives an amine that is a stronger base than aniline.
  3. CReduction of mm-chloronitrobenzene with Sn/HCl gives an amine that is a weaker base than aniline.
  4. DOxidation of mm-methoxytoluene with acidic KMnO4_4 gives an acid weaker than benzoic acid due to the +M+M effect of the methoxy group.

Correct answer

D. Oxidation of mm-methoxytoluene with acidic KMnO4_4 gives an acid weaker than benzoic acid due to the +M+M effect of the methoxy group.

Step-by-step solution

Let us evaluate each statement.

Statement 1 is correct: Oxidation of pp-nitrotoluene yields pp-nitrobenzoic acid. The −NO2-\text{NO}_2 group is a strong electron-withdrawing group (−I,−M-I, -M), making it a stronger acid than pp-fluorobenzoic acid, where fluorine has a weaker net electron-withdrawing effect.

Statement 2 is correct: Reduction of pp-nitroanisole yields pp-anisidine. The −OCH3-\text{OCH}_3 group is an electron-donating group (+M>−I+M > -I), which increases electron density on the nitrogen, making it a stronger base than aniline.

Statement 3 is correct: Reduction of mm-chloronitrobenzene yields mm-chloroaniline. The chlorine atom exerts a −I-I effect, withdrawing electron density and making it a weaker base than aniline.

Statement 4 is incorrect: Oxidation of mm-methoxytoluene yields mm-methoxybenzoic acid. At the meta position, the mesomeric (+M+M) effect of the −OCH3-\text{OCH}_3 group does not operate. Only its inductive (−I-I) effect is felt at the carboxyl group. Because of this −I-I effect, mm-methoxybenzoic acid is actually a stronger acid than benzoic acid, not weaker.

Answer: Oxidation of mm-methoxytoluene with acidic KMnO4_4 gives an acid weaker than benzoic acid due to the +M+M effect of the methoxy group.
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