JEE Advanced · 2022 · 28 Aug 2022 · Paper 1 · Compounds Containing Nitrogen

The reaction sequence involves the conversion of p-nitrotoluene through various intermediates. Based on the solution provided:

(A) Reduction of nitro group using ${\mathrm{H}}_2/\mathrm{Pd}$ gives aniline derivative, diazotization with ${\mathrm{NaNO}}_2/\mathrm{HCl}$, and reduction with ${\mathrm{H}}_3{\mathrm{PO}}_2$ removes the diazo group. Correct.

(B) Reduction with $\mathrm{Sn}/\mathrm{HCl}$ gives aniline, diazotization with ${\mathrm{HNO}}_2$, oxidation with ${\mathrm{KMnO}}_4$ oxidizes the methyl group to carboxylic acid, and ethanol treatment. Correct.

(C) Oxidation first with ${\mathrm{KMnO}}_4$ gives p-nitrobenzoic acid, reduction with ${\mathrm{H}}_2/\mathrm{Pd}$ gives p-aminobenzoic acid. Correct.

The solution diagram confirms all three pathways are valid.