Question:
An organic amine compound 'X' reacts smoothly with Hinsberg's reagent (Benzenesulfonyl chloride) to form a solid precipitate. This precipitate remains completely insoluble when treated with an aqueous sodium hydroxide (\( \text{NaOH} \)) solution. Classify the amine 'X'.
An organic amine compound 'X' reacts smoothly with Hinsberg's reagent (Benzenesulfonyl chloride) to form a solid precipitate. This precipitate remains completely insoluble when treated with an aqueous sodium hydroxide (\( \text{NaOH} \)) solution. Classify the amine 'X'.
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Keep this summary of the Hinsberg test outcomes memorized:
- Primary amine = Reacts, product dissolves in alkali.
- Secondary amine = Reacts, product remains insoluble in alkali.
- Tertiary amine = Does not react with the reagent at all.
Updated On: Jun 3, 2026
- Primary Amine
- Secondary Amine
- Tertiary Amine
- Quaternary Ammonium Salt
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The Correct Option is B
Solution and Explanation
Concept:
The Hinsberg Test is used to distinguish between primary, secondary, and tertiary amines based on how they react with benzenesulfonyl chloride (\( \text{C}_6\text{H}_5\text{SO}_2\text{Cl} \)) and whether the resulting products dissolve in an alkaline solution.
Step 1: Analyze how each type of amine behaves during the test.
Step 2: Match the compound's behavior to the correct category.
Because compound 'X' reacts with the reagent but forms a precipitate that does not dissolve in \( \text{NaOH} \), it matches the characteristic behavior of a Secondary Amine.
Step 1: Analyze how each type of amine behaves during the test.
- Primary Amines: React to form a sulfonamide that retains a highly acidic hydrogen atom on its nitrogen. This acidic hydrogen allows the product to dissolve completely in strong bases like \( \text{NaOH} \).
- Secondary Amines: React with the reagent to form an \( N,N \)-dialkylbenzenesulfonamide product. Because the nitrogen has no remaining acidic hydrogen atoms, this product is completely insoluble in alkali.
- Tertiary Amines: Lack any replaceable hydrogen atoms on the nitrogen and do not react with the test reagent under standard conditions.
Step 2: Match the compound's behavior to the correct category.
Because compound 'X' reacts with the reagent but forms a precipitate that does not dissolve in \( \text{NaOH} \), it matches the characteristic behavior of a Secondary Amine.
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