Carboxylic Acids and their Derivatives 2 Question 52
52. A liquid $X$, having a molecular formula $\mathrm{C}{6} \mathrm{H}{12} \mathrm{O}_{2}$ is hydrolysed with water in the presence of an acid to give a carboxylic acid $Y$ and an alcohol $Z$. Oxidation of $Z$ with chromic acid gives $Y$. What are the structures of $X, Y$ and $Z$ ?
(1986, 3M)
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Solution:
- $X$ is an ester and both its acid and alcohol fragments have same number of carbons. Hence, $X$ is :
$$ \begin{aligned} & \underset{X}{\mathrm{CH}{3} \mathrm{CH}{2} \mathrm{COOCH}{2} \mathrm{CH}{2} \mathrm{CH}{3}} \underset{\mathrm{H}{2} \mathrm{O}}{\mathrm{H}^{+}} \underset{Y}{\mathrm{CH}{3} \mathrm{CH}{2} \mathrm{COOH}} \ & +\mathrm{CH}{3} \mathrm{CH}{2} \mathrm{CH}{2} \mathrm{OH} \ & \mathrm{Z} \xrightarrow{[\mathrm{O}]} \mathrm{CH}{3} \mathrm{CH}_{2} \mathrm{COOH} \end{aligned} $$
