An aromatic compound 'A' with molecular formula C7H7ON undergoes a series of reactions as shown below. Write the structures of A, B, C and D in the following sequence of reactions : Compound (A), molecular formula (C7H7ON), treated with Br2/aq. KOH gives Compound (B); Compound (B

Question

An aromatic compound 'A' with molecular formula C7H7ON undergoes a series of reactions as shown below. Write the structures of A, B, C and D in the following sequence of reactions : Compound (A), molecular formula (C7H7ON), treated with Br2/aq. KOH gives Compound (B); Compound (B) treated with NaNO2 + HCl at 273–278 K gives Compound (C); Compound (C) treated with C6H5-OH gives Compound (D), an orange dye.

Accepted Answer

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> [!TLDR]
> A (C7H7ON) is benzamide, which loses CO via Hofmann bromamide degradation to give aniline (B); diazotisation gives the diazonium salt (C); coupling with phenol gives the orange azo dye (D).
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> The molecular formula $C_7H_7ON$ matches benzamide, $C_6H_5-CO-NH_2$ (A) — one carbonyl O, one amide N, and 7 carbons (6 from the ring + 1 carbonyl carbon).
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