Single correct option
Two geometric isomers of acetophenone oxime are available. The isomer (hydroxyl group on the same side as the phenyl group) is treated with , then the product is boiled with aqueous acid, the mixture is made basic and the amine fraction is separated. The amine is treated with at – and then with alkaline -naphthol. The correct description of the sequence is
- A. Acid hydrolysis gives benzoic acid and methylamine; no azo dye is formed
- B. Acid hydrolysis gives acetic acid and aniline; a scarlet azo dye is formed
- C. Acid hydrolysis gives benzoic acid and methylamine; a scarlet azo dye is formed
- D. Acid hydrolysis gives acetic acid and aniline; no azo dye is formed
Show answer and solution
Answer: (A) Acid hydrolysis gives benzoic acid and methylamine; no azo dye is formed
In the Beckmann rearrangement the group anti to the leaving group on nitrogen (the activated group) migrates from carbon to nitrogen. In the isomer the hydroxyl group is syn to phenyl, so it is anti to the methyl group. The methyl group therefore migrates, and after loss of the leaving group and capture by water the product is the amide (N-methylbenzamide), not acetanilide. Acid hydrolysis then gives benzoic acid and methylammonium ion. Diazotisation works usefully only for aromatic primary amines: aliphatic diazonium ions decompose at once to alcohols or alkenes with loss of , so no diazonium salt survives for coupling and no azo dye forms with -naphthol. The isomer would instead give acetanilide, then aniline, a stable benzenediazonium salt and a scarlet azo dye. Hence option (A).
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