Amongst the compounds given, the one that would form a brilliant coloured dye on treatment with NaNO_2 in dilute HCl followed by addition to an alkaline solution of -naphthol is: [IIT JEE 2011]

JEE Main Chemistry question

Amongst the compounds given, the one that would form a brilliant coloured dye on treatment with in dilute HCl followed by addition to an alkaline solution of -naphthol is: [IIT JEE 2011]

(A)-dimethylaniline,
(B)an -substituted secondary/tertiary aromatic amine lacking a free (e.g. -methyldiphenylamine-type)
(C)-toluidine, Correct
(D)benzylamine,

Answer: (C)

Solution

Forming an azo dye with alkaline -naphthol requires diazotisation to a stable aryl diazonium salt, which needs a primary aromatic amine (). -dimethylaniline is a tertiary aromatic amine (no free ; it instead undergoes -nitrosation at the para position with ). The compound in

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Question ID VK-150274