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In the following sequence of reactions starting from benzene, identify the major product S: Benzene -> (i) HNO3/H2SO4, (ii) Sn/HCl -> P -> CH3COCl/Pyridine -> Q -> (i) conc. H2SO4, (ii) HNO3/H2SO4 -> R -> (i) dil. H2SO4, heat, (ii) NaOH -> S

1. (A) 2-nitroaniline (NH2 at position 1, NO2 at ortho position 2)
2. (B) 4-nitroaniline (NH2 at position 1, NO2 at para position 4)
3. (C) 2-hydroxy-4-nitroaniline (NH2 at 1, OH at 2, NO2 at 4)
4. (D) 2-nitro-4-sulfoaniline (NH2 at 1, NO2 at 2, SO3H at 4)

Correct answer: (A) 2-nitroaniline (NH2 at position 1, NO2 at ortho position 2)

Solution

Benzene is nitrated then reduced to aniline (P). Acetylation gives acetanilide (Q), protecting -NH2. Sulfonation (conc. H2SO4) places -SO3H at the para position, then nitration (HNO3/H2SO4) goes to the ortho position to give R (2-nitro-4-sulfo-acetanilide). Dil. H2SO4/heat causes desulfonation and NaOH hydrolyzes the acetamide, yielding 2-nitroaniline (S).

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