Q67 / 180 · NEET 2026 (Re-NEET) · Chemistry

Given below are two statements:
Statement-I : Oxidation of $p$-nitrotoluene with acidic KMnO$_4$ gives an acid that is stronger than benzoic acid.
Statement-II : Reduction of $p$-nitrotoluene with Sn/HCl followed by neutralization gives an amine that is more basic than aniline.
In light of the above statements, choose the most appropriate answer from the options given below:

  • A
    Statement-I is incorrect but Statement-II is correct.
  • Correct answer
    B
    Both Statement-I and Statement-II are correct.
  • C
    Both Statement-I and Statement-II are incorrect.
  • D
    Statement-I is correct but Statement-II is incorrect.

Solution

Oxidation of $p$-nitrotoluene with acidic $\text{KMnO}_4$ oxidizes the methyl group to a carboxylic acid group, yielding $p$-nitrobenzoic acid. The $-\text{NO}_2$ group is an electron-withdrawing group ($-I$ and $-M$ effects), which stabilizes the conjugate base (carboxylate ion). Hence, $p$-nitrobenzoic acid is a stronger acid than benzoic acid. Statement-I is correct.

Reduction of $p$-nitrotoluene with $\text{Sn}/\text{HCl}$ reduces the nitro group to an amino group, yielding $p$-toluidine ($p$-methylaniline). The $-\text{CH}_3$ group is an electron-donating group ($+I$ and hyperconjugation effects), which increases the electron density on the nitrogen atom and stabilizes the conjugate acid. Hence, $p$-toluidine is more basic than aniline. Statement-II is correct.

Both Statement-I and Statement-II are correct.

Answer: Both Statement-I and Statement-II are correct.

Hence, the correct answer is option: 'B'.

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