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COMEDK2025ChemistryCarboxylic Acid DerivativesActual

An organic compound [X] (Molecular formula C ₆ H ₁₂ O ₂ ) reacts with dil. H ₂ SO ₄ to form an alcohol [B] and a carboxylic acid [C]. Reaction of compound [ B ] with Jones reagent yielded compound [ C ] . When compound [ C ] was heated with P ₂ O ₅ an Anhydride was formed. Compound [ X ] is ________.

Options

  1. ACH ₃- COO - C - ( CH ₃ )₃
  2. BCH ₃- COO - ( CH ₂ )₃- CH ₃
  3. CCH ₃- COO - CH ₂- CH - ( CH ₃ )₂
  4. DC ₂ H ₅- COO - ( CH ₂ )₂- CH ₃

Correct answer

D. C ₂ H ₅- COO - ( CH ₂ )₂- CH ₃

Step-by-step solution

The molecular formula C ₆ H ₁₂ O ₂ corresponds to an ester. Hydrolysis of an ester RCOOR ' with dilute H ₂ SO ₄ yields a carboxylic acid RCOOH and an alcohol R ' OH . Given that the alcohol [B] is oxidized by Jones reagent to the carboxylic acid [C], it implies that the alcohol [B] and the acid [C] must contain the same number of carbon atoms. Since the total number of carbons in the ester is 6, the acid and the alcohol must each contain 3 carbons. The acid [C] is propanoic acid ( CH ₃ CH ₂ COOH ) and the alcohol [

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