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An organic compound [A], molecular formula $C_{10} H_{20} O_{2}$ was hydrolyzed with dilute sulphuric acid to give a carboxylic aicd [B] and an alcohol [C]. Oxidation of [C] with ${CrO}_{3} - H_{2} {SO}_{4}$ produced [B]. Which of the following structures are not possible for [A]?

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${CH}_{3} {CH}_{2} {CH}_{2} {COOCH}_{2} {CH}_{2} {CH}_{2} {CH}_{3}$

${({CH}_{3})}_{3} - C - {COOCH}_{2} C {({CH}_{3})}_{3}$

answer is C.

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Detailed Solution

${CH}_{3} - {CH}_{2} {CH}_{2} - {COOCH}_{2} - {CH}_{2} - {CH}_{2} - {CH}_{3} [C_{8} H_{6} O_{2}] M . F of A is (C_{6} H_{20} O_{2})$

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