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Question 50

Given below are two statements : Statement (I) : All the following compounds react with p-toluenesulfonyl chloride. $$C_6H_5NH_2$$, $$(C_6H_5)_2NH$$, $$(C_6H_5)_3N$$. Statement (II) : Their products in the above reaction are soluble in aqueous NaOH. In the light of the above statements, choose the correct answer from the options given below :

We need to evaluate both statements about the Hinsberg test (reaction with p-toluenesulfonyl chloride, TsCl).

Statement (I): All the following compounds react with TsCl: $$C_6H_5NH_2$$ (aniline, primary amine), $$(C_6H_5)_2NH$$ (diphenylamine, secondary amine), $$(C_6H_5)_3N$$ (triphenylamine, tertiary amine).

In the Hinsberg test:

- Primary amines react with TsCl to form sulfonamides (N-monosubstituted).

- Secondary amines react with TsCl to form sulfonamides (N,N-disubstituted).

- Tertiary amines do not react with TsCl because they have no N-H bond to undergo substitution.

Since $$(C_6H_5)_3N$$ (a tertiary amine) does not react with TsCl, Statement I is false.

Statement (II): Their products in the above reaction are soluble in aqueous NaOH.

For primary amines, the product (N-monosubstituted sulfonamide) has an acidic N-H and is soluble in NaOH. For secondary amines, the product (N,N-disubstituted sulfonamide) has no acidic N-H and is insoluble in NaOH. Since not all products are soluble in NaOH, Statement II is also false.

The correct answer is Option 4: Both Statement I and Statement II are false.

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