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Question 49

Which among the following represent reagent 'A'?

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The given reaction is an azo coupling reaction. The benzenediazonium chloride salt acts as a weak electrophile that reacts with highly electron-rich aromatic compounds.

The reaction takes place in a basic medium ($NaOH$). The base is crucial because it deprotonates the hydroxyl group of the incoming reagent to form a highly reactive, strongly nucleophilic anion (like a phenoxide or naphthoxide ion).

To produce a specifically orange-red dye, the required reagent 'A' is $\beta$-naphthol (also known as 2-naphthol). The electrophilic coupling takes place specifically at the 1-position of the naphthol ring, yielding 1-(phenylazo)-2-naphthol. This intense orange-red precipitate is the basis of the classic laboratory azo-dye test for primary aromatic amines.

(For context, coupling this diazonium salt with phenol typically yields a lighter orange dye, while coupling with aniline in an acidic medium yields a yellow dye).

The correctly marked structure in the first box is $\beta$-naphthol.

Correct Reagent 'A': $$\beta$$-naphthol (2-naphthol)

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