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Consider the following amines: (a) CH3CH2-NH2, (b) CH3-NH-CH3, (c) (C2H5)3N, (d) PhNH2, (e) C6H5NHCH3, (f) (CH3)2CHNH2, (g) CH3CH2NHCH2CH3. Find (X + Y + Z) where: X = number of amines that give a foul-smelling poisonous gas on treatment with CHCl3/KOH (carbylamine reaction); Y = number of amines that produce an oily yellow-coloured nitroso compound when treated with aqueous HNO2; Z = number of amines whose product with Ph-SO2Cl is soluble in aqueous KOH.

1. (A) 3
2. (B) 6
3. (C) 9
4. (D) 12

Correct answer: (C) 9

Solution

Carbylamine reaction: only primary amines (a, d, f) => X = 3. Yellow oily nitroso compounds: only secondary amines (b, e, g) => Y = 3. Hinsberg test (product soluble in KOH): primary amines form N-substituted sulphonamide (still has N-H, hence acidic, dissolves in KOH); amines a, d, f are primary => Z = 3. Total = 3 + 3 + 3 = 9.

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