Q.

An organic compound A has molecular formula C7H9 N and it forms a clear solution when dissolved in aqueous KOH solution of benzene sulphonyl chloride. A on treatment with NaNO2 and HCI at 0oC and then with 2-naphthol forms an intensely coloured compound. Also A on treatment with CH3COCl followed by electrophilic substitution yields a single product. Identify A.

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a

4-methylaniline

b

2-methylaniline

c

3-methylaniline

d

N-methylaniline

answer is A.

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Detailed Solution

Formation of single product in electrophilic substitution reaction indicates the symmetrical structure, (i.e. p-substitution) of A. Formation of dye stuff with NaNO2/HCl 0oC and 2-naphthol suggests that it is an aromatic primary amine. Thus, possible structure of A is
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