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:
B. Both Statement-I and Statement-II are correct.
Oxidation of p-nitrotoluene with acidic KMnO _4 oxidizes the methyl group to a carboxylic acid group, yielding p-nitrobenzoic acid. The - 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 Sn / HCl reduces the nitro group to an amino group, yielding p-toluidine (p-methylaniline). The - 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.
Related: Chemistry — Carboxylic Acid Derivatives · All PYQ Banks