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.
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.
- Both Statement I and Statement II is false
- Statement I is true but Statement II is false
- Statement I is false but Statement II is true
- Both Statement I and Statement II is true
The Correct Option is A
Approach Solution - 1
To solve the given problem, we need to analyze the two statements provided with respect to the chemical reactivity of the compounds with p-toluenesulfonyl chloride and the solubility of the resultant products in aqueous NaOH.
Analysis of Statement I:
Statement I claims that: "All the following compounds react with p-toluenesulfonyl chloride."
The compounds listed are: \(C_6H_5NH_2\) (aniline), \((C_6H_5)_2NH\) (diphenylamine), and \((C_6H_5)_3N\) (triphenylamine).
Explanation:
- Aniline (\(C_6H_5NH_2\)): A primary amine, reacts with p-toluenesulfonyl chloride to form a tosylamide.
- Diphenylamine (\((C_6H_5)_2NH\)): A secondary amine, can react to form a tosyl derivative but typically less reactive than primary amines.
- Triphenylamine (\((C_6H_5)_3N\)): A tertiary amine, which generally does not react with p-toluenesulfonyl chloride under normal conditions.
Therefore, Statement I is false because triphenylamine does not react with p-toluenesulfonyl chloride.
Analysis of Statement II:
Statement II claims that: "Their products in the above reaction are soluble in aqueous NaOH."
Explanation:
- The products of aniline and diphenylamine reacting with p-toluenesulfonyl chloride are tosylamides.
- Tosylamides are generally not soluble in aqueous NaOH as they do not possess acidic hydrogens that can result in salt formation.
Thus, Statement II is false because the products are not soluble in aqueous NaOH.
Conclusion:
The correct answer is: "Both Statement I and Statement II is false".
Approach Solution -2
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.
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