In the following sequence of reactions a compound A, (molecular formula \(\mathrm{C_6H_{12}O_2}\)) with a straight chain structure gives a \(\mathrm{C_4}\) carboxylic acid. A is :
\(\mathrm{A}\ \xrightarrow[\mathrm{H_3O^+}]{\mathrm{LiAlH_4}}\ \mathrm{B}\ \xrightarrow{\text{Oxidation}}\ \mathrm{C_4}\text{-carboxylic acid}\)
\(\mathrm{A}\ \xrightarrow[\mathrm{H_3O^+}]{\mathrm{LiAlH_4}}\ \mathrm{B}\ \xrightarrow{\text{Oxidation}}\ \mathrm{C_4}\text{-carboxylic acid}\)
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- \(\mathrm{CH_3-CH_2-COO-CH_2-CH_2-CH_3}\)
- \(\mathrm{CH_3-CH_2-CH_2-COO-CH_2-CH_3}\)
- \(\mathrm{CH_3-CH_2-CH_2-O-CH=CH-CH_2-OH}\)
The Correct Option is C
Solution and Explanation
(1) Propyl propanoate gives 2 propan-1-ol, so a \(\mathrm{C_3}\) acid only: rejected.
(3) Ethyl butanoate \(\mathrm{CH_3CH_2CH_2COOC_2H_5}\) gives butan-1-ol + ethanol; oxidation gives butanoic acid (\(\mathrm{C_4}\)): fits.
(2) is a hydroxy ether and (4) an enol ether alcohol, neither an ester; \(\mathrm{LiAlH_4}\) does not cleave them to give a \(\mathrm{C_4}\) acid: rejected.
Answer: (3) \(\mathrm{CH_3-CH_2-CH_2-COO-CH_2-CH_3}\)
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