Single correct option
A compound gives an alkali-soluble product with benzenesulfonyl chloride, forms an orange dye when diazotised at and added to alkaline -naphthol, and shows only two doublets in the aromatic region of its H NMR spectrum. The compound is
- A. 4-Methylaniline
- B. Benzylamine
- C. 2-Methylaniline
- D. 3-Methylaniline
Show answer and solution
Answer: (A) 4-Methylaniline
Alkali-soluble sulfonamide means a primary amine (Hinsberg test). Benzylamine is primary but its diazonium salt, being aliphatic, decomposes with loss to the alcohol and cannot couple, so the dye test excludes it. Of the toluidines, only the para isomer has a symmetric 1,4-disubstituted ring, which gives the pattern of two doublets; the ortho and meta isomers show four distinct aromatic protons. Hence 4-methylaniline (p-toluidine).
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