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JEE Main · 2022 · 26 Jun 2022 · Shift 2 · Compounds Containing Nitrogen

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Which statement is NOT correct for p-toluenesulphonyl chloride?
  1. (A)It is known as Hinsberg's reagent.
  2. (B)It is used to distinguish primary and secondary amines.
  3. (C)On treatment with secondary amine, it leads to a product, that is soluble in alkali.✓ Correct
  4. (D)It doesn't react with tertiary amines.

Answer: (C)

Solution

p-Toluenesulphonyl chloride (Hinsberg's reagent) is used to distinguish between primary, secondary, and tertiary amines. Primary amines form sulfonamides that are soluble in alkali (due to acidic N-H). Secondary amines form sulfonamides that are NOT soluble in alkali (no acidic H on N). Tertiary amines do not react. Therefore, statement (C) is incorrect — the product from secondary amine is insoluble in alkali.

JEE Main · 2022 · 26 Jun 2022 · Shift 2 · Single correct option

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