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COMEDK · Chemistry · 28. Carboxylic Acid Derivatives

A sweet smelling organic compound \([\mathrm{A}]\left(\mathrm{C}_9 \mathrm{H}_{10} \mathrm{O}_2\right)\) undergoes acid hydrolysis to form an acid [B].

Compound [B] further reacts with Ammonia followed by heating to yield [C].

Compound \([\mathrm{C}]\) when reacted with \(\mathrm{Br}_2\) in caustic potash gave compound \([\mathrm{D}]\left(\mathrm{C}_6 \mathrm{H} 7 \mathrm{~N}\right)\) which gives a white precipitate with aqueous \(\mathrm{Br}_2\).

Identify compounds \([\mathrm{A}]\) & \([\mathrm{D}]\)

  1. A A: Methyl benzoate
    D: Aniline
  2. B A: Ethyl heptanoate
    D: N-ethylbutanamine
  3. C A: Ethyl benzoate
    D: Aniline
  4. D A: Methyl Pentanoate
    D: N-methylpentanamine
Verified Solution

Answer & Solution

Correct Answer

(C) A: Ethyl benzoate
D: Aniline

Step-by-step Solution

Detailed explanation

Compound [A] has the molecular formula \(\mathrm{C}_9\mathrm{H}_{10}\mathrm{O}_2\). Acid hydrolysis of [A] yields an acid [B]. Since [A] is a sweet-smelling ester, it is likely an ester of benzoic acid. Ethyl benzoate (\(\mathrm{C}_6\mathrm{H}_5\mathrm{COOCH}_2\mathrm{CH}_3\))…