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Q.

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] ?

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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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