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Question 48

Isomeric amines with molecular formula C$$_8$$H$$_{11}$$N give the following tests
Isomer P $$\Rightarrow$$ Can be prepared by Gabriel phthalimide synthesis
Isomer Q $$\Rightarrow$$ Reacts with Hinsberg's reagent to give solid insoluble in NaOH
Isomer R $$\Rightarrow$$ Reacts with HONO followed by $$\beta$$-naphthol in NaOH to give red dye.
Isomers P, Q and R respectively are

Gabriel phthalimide synthesis:Look for a primary amine where the -NH2 group is attached to an aliphatic carbon chain instead of the benzene ring directly.

Hinsberg's reagent:Secondary amines react with Hinsberg's reagent to give a solid that is insoluble in NAOH.

primary aromatic amines give red dye.

hence answer would be D

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