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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−H2SO4produced [B]. Which of the following structures are not possible for [A]?

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a

b

c

CH3CH2CH2COOCH2CH2CH2CH3

d

CH33−C−COOCH2CCH33

answer is C.

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Detailed Solution

CH3−CH2CH2−COOCH2−CH2−CH2−CH3C8H6O2 M.F of A is C6H20O2

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