Compound 'A ’ was prepared by oxidation of compound 'B ’ with alk… - Vidyadip

Question

Compound $'A\ ’$ was prepared by oxidation of compound $'B\ ’$ with alkaline $\ce{KMnO_4}.$ Compound $'A\ ’$ on reduction with lithium aluminium hydride gets converted back to compound $'B\ ’.$ When compound $'A\ ’$ is heated with compound $B$ in the presence of $\ce{H_2SO_4}$ it produces fruity smell of compound $C$ to which family the compounds $'A\ ’, 'B\ ’$ and $'C\ ’$ belong to?

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Answer

$'A\ '$ is carboxylic acid $\ce{(R-COOH)}, 'B\ '$ is an alcohol $\ce{(R-CH_2OH)}$ and $'C\ '$ is an ester $\ce{(RCH_2-COOR)}$
$\text{R}-\text{CH}_2\text{OH}\xrightarrow{\text{Oxidation (KMn O}_4)}\text{R}-\text{COOH}\\\ \ \ \ \ \ \ \ \ ^\text{(B)}\ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ \ ^\text{(A)}$
$\text{Alcohol (B)}\xleftarrow{\text{LiAlH}_4,\text{reduction}}\text{Carboxylic acid (A)}$

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