Question

Given below are two statements:
Statement (I) : All the following compounds react with p-toluenesulfonyl chloride.
$C_6H_5NH_2 \quad      (C_6H_5)_2NH                \quad (C_6H_5)_3N$
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.

• A. Both Statement I and Statement II is false
• B. Statement I is true but Statement II is false
• C. Statement I is false but Statement II is true
• D. Both Statement I and Statement II is true

Answer 1

The Correct Option is A

The reaction with p-toluenesulfonyl chloride (TsCl) is known as the Hinsberg test, which is specific for 1$^\circ$ amines.
Only 1$^\circ$ amines (C$_6$H$_5$NH$_2$) react with TsCl to form sulfonamides that are soluble in aqueous NaOH.
2$^\circ$ amines ((C$_6$H$_5$)$_2$NH) react with TsCl to form sulfonamides that are insoluble in NaOH.
3$^\circ$ amines ((C$_6$H$_5$)$_3$N) do not react with TsCl at all.
Thus:
Statement I: False. Not all the given compounds react with TsCl.
Statement II: False. Only the sulfonamide formed by 1$^\circ$ amines is soluble in NaOH.