An organic compound [A], molecular formula \(\mathrm{C_{10}H_{20}O_2}\) was hydrolyzed with dilute sulphuric acid to give a carboxylic acid [B] and an alcohol [C]. Oxidation of [C] with \(\mathrm{CrO_3 - H_2SO_4}\) produced [B]. Which of the following strucutres are not possible for [A]?
Show Hint
- \(\mathrm{(CH_3)_3-C-COOCH_2C(CH_3)_3}\)
- \(\mathrm{CH_3CH_2CH_2COOCH_2CH_2CH_2CH_3}\)
The Correct Option is B
Solution and Explanation
(1) pivalic acid + neopentyl alcohol (both 5 C, alcohol primary and oxidises to pivalic acid): possible.
(2) butanoic acid + butan-1-ol: formula is \(\mathrm{C_8H_{16}O_2}\), not \(\mathrm{C_{10}H_{20}O_2}\) (4 C + 4 C): not possible.
(3) 2-methylbutanoic acid + 2-methylbutan-1-ol: 5 C + 5 C, \(\mathrm{C_{10}H_{20}O_2}\), alcohol primary and oxidises to 2-methylbutanoic acid: possible.
(4) 3-methylpentanoic acid (6 C) + butan-2-ol (4 C, a secondary alcohol that gives a ketone, not the acid): not possible.
Not possible: options (2) and (4).
Answer: (2) and (4)
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