Question

Compound P is neutral. Q gives effervescence with NaHCO₃ while R reacts with Hinsbergs reagent to give solid soluble in NaOH. Compound P is

• A.
• B.
• C.
• D.

Answer 1

The Correct Option is D

Given Data:

• Compound P is neutral.
• Residue Q gives effervescence with NaHCO₃, suggesting the presence of a carboxylic acid group (-COOH).
• Filtrate gives oily liquid R, which reacts with Hinsberg’s reagent to give a solid soluble in NaOH, indicating the presence of a primary amine (-NH₂).
• Molecular formula of P: C₁₄H₁₃ON.

Analysis:

• Compound P must be a neutral amide because it is neutral and contains both oxygen and nitrogen in its molecular formula.
• Upon hydrolysis with HCl, the amide breaks down to give:
  • Residue Q: A carboxylic acid (gives effervescence with NaHCO₃).
  • Filtrate R: A primary amine (reacts with Hinsberg’s reagent to form a solid soluble in NaOH).

Correct Option:

The correct compound P is Option (4):

• Structure of Option (2) corresponds to the amide with a molecular formula of C₁₄H₁₃ON.
• Upon hydrolysis, it produces a carboxylic acid (Q) and a primary amine (R), satisfying all the given conditions.

Conclusion: The correct answer is Option 2.