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Hinsberg reagent is benzenesulfonyl chl...

Hinsberg reagent is benzenesulfonyl chloride. In aqueous KOH this reacts with primary amine `(RNH_(2))` to give a clear solution which on acidification gives a white precipitate, which is due to the formation of

A

`R-NHSO_(2)C_(6)H_(5)`

B

`C_(6)H_(5)SO_(2)NH_(2)`

C

`R-N-SO_(2)C_(6)H_(5)K^(+)`

D

`R-overset(N)overset(|)underset(H)underset(|)(N^(+))-SO_(2)C_(6)H_(5)OH^(-)`

Text Solution

AI Generated Solution

The correct Answer is:
To solve the question regarding the reaction of Hinsberg reagent (benzenesulfonyl chloride) with a primary amine (RNH₂) in aqueous KOH, we can follow these steps: ### Step-by-Step Solution: 1. **Identify the Reactants**: - The Hinsberg reagent is benzenesulfonyl chloride (C₆H₅SO₂Cl). - The primary amine is represented as RNH₂. 2. **Reaction with Aqueous KOH**: - When benzenesulfonyl chloride reacts with a primary amine in the presence of aqueous KOH, the amine acts as a nucleophile. The nitrogen atom in the amine has a lone pair of electrons that can attack the electrophilic sulfur atom in the sulfonyl chloride. 3. **Formation of the Sulfonamide**: - The nucleophilic attack leads to the formation of a sulfonamide intermediate. The chlorine atom is displaced as a good leaving group (Cl⁻), resulting in the formation of RNH-SO₂-C₆H₅ (the sulfonamide). 4. **Formation of a Clear Solution**: - The reaction produces a clear solution due to the formation of the sulfonamide, which is soluble in the aqueous medium. 5. **Acidification**: - Upon acidification (adding H⁺ ions), the sulfonamide can protonate the nitrogen atom, leading to the formation of a positively charged sulfonamide complex. 6. **Precipitation of the Sulfonamide**: - The protonation of the sulfonamide results in decreased solubility, leading to the formation of a white precipitate. This precipitate is the sulfonamide RNH-SO₂-C₆H₅. 7. **Conclusion**: - The white precipitate formed upon acidification is due to the formation of the sulfonamide, which can be represented as RNH-SO₂-C₆H₅. ### Final Answer: The white precipitate formed upon acidification is due to the formation of **RNH-SO₂-C₆H₅ (sulfonamide)**. ---
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