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An organic compound [A], molecular formula C10H20O2 was hydrolyzed with dilute sulphuric acid to give a carboxylic acid [B] and an alcohol [C]. Oxidation of [C] with CrO3 – H2SO4 produced [B]. Which of the following structure are not possible for [A] ?

1. CH3CH2CH2COOCH2CH2CH3
2. CH3 – CH2 – CH(CH3) – COOCH2 – CH(CH3) – CH2CH3
3. (CH3)3 – C – COOCH2C(CH3)3
4. CH3 – CH2 – CH(CH3) – OCOCH2CH(CH3)CH2CH3

Correct answer: CH3CH2CH2COOCH2CH2CH3

Solution

The structure CH3CH2CH2COOCH2CH2CH3 cannot produce a carboxylic acid and an alcohol upon hydrolysis because it lacks a suitable functional group that would yield a corresponding alcohol upon oxidation, making it incompatible with the requirements of the reaction.

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