NEET
- Exam
- NEET
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- 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
- AOxidation of -nitrotoluene with acidic KMnO gives an acid stronger than -fluorobenzoic acid.
- BReduction of -nitroanisole with Sn/HCl gives an amine that is a stronger base than aniline.
- CReduction of -chloronitrobenzene with Sn/HCl gives an amine that is a weaker base than aniline.
- DOxidation of -methoxytoluene with acidic KMnO gives an acid weaker than benzoic acid due to the effect of the methoxy group.
Correct answer
D. Oxidation of -methoxytoluene with acidic KMnO gives an acid weaker than benzoic acid due to the effect of the methoxy group.
Step-by-step solution
Let us evaluate each statement.
Statement 1 is correct: Oxidation of -nitrotoluene yields -nitrobenzoic acid. The group is a strong electron-withdrawing group (), making it a stronger acid than -fluorobenzoic acid, where fluorine has a weaker net electron-withdrawing effect.
Statement 2 is correct: Reduction of -nitroanisole yields -anisidine. The group is an electron-donating group (), which increases electron density on the nitrogen, making it a stronger base than aniline.
Statement 3 is correct: Reduction of -chloronitrobenzene yields -chloroaniline. The chlorine atom exerts a effect, withdrawing electron density and making it a weaker base than aniline.
Statement 4 is incorrect: Oxidation of -methoxytoluene yields -methoxybenzoic acid. At the meta position, the mesomeric () effect of the group does not operate. Only its inductive () effect is felt at the carboxyl group. Because of this effect, -methoxybenzoic acid is actually a stronger acid than benzoic acid, not weaker.
Answer: Oxidation of -methoxytoluene with acidic KMnO gives an acid weaker than benzoic acid due to the effect of the methoxy group.
Statement 1 is correct: Oxidation of -nitrotoluene yields -nitrobenzoic acid. The group is a strong electron-withdrawing group (), making it a stronger acid than -fluorobenzoic acid, where fluorine has a weaker net electron-withdrawing effect.
Statement 2 is correct: Reduction of -nitroanisole yields -anisidine. The group is an electron-donating group (), which increases electron density on the nitrogen, making it a stronger base than aniline.
Statement 3 is correct: Reduction of -chloronitrobenzene yields -chloroaniline. The chlorine atom exerts a effect, withdrawing electron density and making it a weaker base than aniline.
Statement 4 is incorrect: Oxidation of -methoxytoluene yields -methoxybenzoic acid. At the meta position, the mesomeric () effect of the group does not operate. Only its inductive () effect is felt at the carboxyl group. Because of this effect, -methoxybenzoic acid is actually a stronger acid than benzoic acid, not weaker.
Answer: Oxidation of -methoxytoluene with acidic KMnO gives an acid weaker than benzoic acid due to the effect of the methoxy group.