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COMEDK · Chemistry · 28. Carboxylic Acid Derivatives

An organic compound [X] (Molecular formula \(\mathrm{C}_6 \mathrm{H}_{12} \mathrm{O}_2\) ) reacts with dil. \(\mathrm{H}_2 \mathrm{SO}_4\) to form an alcohol [B] and a carboxylic acid [C]. Reaction of compound \([\mathrm{B}]\) with Jones reagent yielded compound \([\mathrm{C}]\). When compound \([\mathrm{C}]\) was heated with \(\mathrm{P}_2 \mathrm{O}_5\) an Anhydride was formed. Compound \([\mathrm{X}]\) is ________.

  1. A \(\mathrm{CH}_3-\mathrm{COO}-\mathrm{C}-\left(\mathrm{CH}_3\right)_3\)
  2. B \(\mathrm{CH}_3-\mathrm{COO}-\left(\mathrm{CH}_2\right)_3-\mathrm{CH}_3\)
  3. C \(\mathrm{CH}_3-\mathrm{COO}-\mathrm{CH}_2-\mathrm{CH}-\left(\mathrm{CH}_3\right)_2\)
  4. D \(\mathrm{C}_2 \mathrm{H}_5-\mathrm{COO}-\left(\mathrm{CH}_2\right)_2-\mathrm{CH}_3\)
Verified Solution

Answer & Solution

Correct Answer

(D) \(\mathrm{C}_2 \mathrm{H}_5-\mathrm{COO}-\left(\mathrm{CH}_2\right)_2-\mathrm{CH}_3\)

Step-by-step Solution

Detailed explanation

The molecular formula \(\mathrm{C}_6 \mathrm{H}_{12} \mathrm{O}_2\) corresponds to an ester. Hydrolysis of an ester \(\mathrm{RCOOR}'\) with dilute \(\mathrm{H}_2 \mathrm{SO}_4\) yields a carboxylic acid \(\mathrm{RCOOH}\) and an alcohol \(\mathrm{R}'\mathrm{OH}\). Given that…