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JEE Main 2024 · Chemistry · Carbonyl Compounds, Carboxylic Acids and Amines · medium

Among all the isomeric amines of molecular formula C7H9N that contain a benzene ring, the number of isomers that give a positive carbylamine test and…

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Among all the isomeric amines of molecular formula C7H9N\mathrm{C_7H_9N} that contain a benzene ring, the number of isomers that give a positive carbylamine test and also form an azo dye when their NaNO2/HCl\mathrm{NaNO_2/HCl} (273 K) product is added to alkaline 2-naphthol is
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Answer: 3

Benzene-ring isomers of C7H9N\mathrm{C_7H_9N}: benzylamine, oo-, mm- and pp-toluidine, and N-methylaniline. The carbylamine test needs a primary amine, which excludes N-methylaniline (secondary): leaving 44 primary amines. Coupling with 2-naphthol needs a stable arenediazonium salt at 273 K, which only aromatic primary amines (the three toluidines) provide; benzylamine gives an unstable aliphatic-type diazonium ion that decomposes to benzyl alcohol and N2\mathrm{N_2}. Count =3=3.
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