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Q.

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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a

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b

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c

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d

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answer is C.

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Detailed Solution

Organic Compound A is an ester because acid hydrolysis produces a mixture of acids and alcohols. Oxidation of alcohol gives acid . Therefore, have the same carbon number. The ester has 8 carbon atoms. Therefore, both carboxylic acid and alcohol must contain 4 carbon atoms each. Dehydration of alcohol C gives but-1-ene. Therefore, C must be a straight chain alcohol. Oxidation of butan-1-ol gives butanoic acid.

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