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Consider the following two statements about the reaction of amines with p-toluenesulfonyl chloride (TsCl): Statement I: All three compounds — aniline (C6H5NH2), diphenylamine ((C6H5)2NH), and triphenylamine ((C6H5)3N) — react with TsCl. Statement II: The products formed in the above reaction are soluble in aqueous NaOH. Choose the correct option.

1. Both Statement I and Statement II are false
2. Statement I is true but Statement II is false
3. Statement I is false but Statement II is true
4. Both Statement I and Statement II are true

Correct answer: Both Statement I and Statement II are false

Solution

Statement I is false because triphenylamine ((C6H5)3N) has no N-H bond, so it does not react with TsCl. Only primary and secondary amines react. Statement II is false because only the sulfonamide from a primary amine is acidic enough (N-H remains) to dissolve in aqueous NaOH; the sulfonamide from a secondary amine has no N-H and is insoluble in NaOH.

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