Number of amine compounds from the following giving solids which are soluble in NaOH upon reaction with Hinsberg's reagent is . [figure]
Answer
5
Solution
Hinsberg's reagent (C6H5SO2Cl) with a 1° amine:
RNH2 + C6H5SO2Cl C6H5SO2NHR
This sulphonamide still has an acidic N–H, so the solid dissolves in NaOH; only 1° amines do this.
1° amines here: aniline, 4-aminodiphenylamine, 2-methoxyaniline, propan-1-amine and cyclohexanamine = 5
Not counted: benzamide, semicarbazide and urea (amides, not amines); N-methylaniline (2°, its solid is insoluble in NaOH); the two 3° amines (no reaction).
Answer: 5