Question:

The reaction of Toluenesulfonyl chloride with a primary amine forms a product that is:

Show Hint

Hinsberg Test: Primary amine $\rightarrow$ Product soluble in alkali Secondary amine $\rightarrow$ Product insoluble in alkali Tertiary amine $\rightarrow$ No sulfonamide formation
Updated On: Jun 17, 2026
  • Soluble in alkali
  • Insoluble in alkali
  • Soluble in water but insoluble in acids
  • Liquid at room temperature
Show Solution
collegedunia
Verified By Collegedunia

The Correct Option is A

Solution and Explanation

Concept: The reaction of amines with p-toluenesulfonyl chloride is known as the Hinsberg test. This test is used to distinguish primary, secondary and tertiary amines.

Step 1:
Reaction of primary amine with Hinsberg reagent. A primary amine reacts with p-toluenesulfonyl chloride. \[ \mathrm{RNH_2 + TsCl} \rightarrow \mathrm{TsNHR} \] where Ts represents the tosyl group.

Step 2:
Nature of the product. The product still contains an acidic hydrogen attached to nitrogen. Hence it can react with alkali. \[ \mathrm{TsNHR + NaOH} \rightarrow \mathrm{Soluble\ sodium\ salt} \]

Step 3:
Consequence. Because the sodium salt is formed, the product dissolves in alkali. Therefore the product is soluble in alkali. \[ \boxed{\text{Option (1)}} \]
Was this answer helpful?
0
0