Let's deduce the reaction sequence in reverse:
- Compound D: Given as N-methyl aniline (C6H5−NH−CH3), which is a secondary amine.
- Compound C: Formed by the reaction of B with CHCl3 and KOH, and upon reduction gives D. The reaction of a primary amine with CHCl3/KOH is the Carbylamine reaction, which yields an isocyanide (R−NC). Reduction of an isocyanide (R−NC+4[H]→R−NH−CH3) always produces a secondary amine with one methyl group. Since D is N-methyl aniline, C must be phenyl isocyanide (C6H5−NC).
- Compound B: Since B undergoes the carbylamine reaction to form phenyl isocyanide, B must be the corresponding primary aromatic amine, aniline (C6H5−NH2).
- Compound A: A is reduced to form aniline (B). The most common precursor that yields aniline upon reduction is nitrobenzene (C6H5−NO2).
Therefore, the structure of A is nitrobenzene.