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An organic compound (A) (molecular formu...

An organic compound (A) (molecular formula `C_(8)H_(16)O_(2))` was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C ). Oxidation of (C ) with chromic acid produced (B). (C ) on dehydration gives but-1-ene. Write equations for the reactions involved.

Text Solution

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(i) Since but-1-ene has been formed as a result of dehydration of alcohol, the alcohol 'C' must contain four carbon atoms.
(ii) Since the alcohol 'C' upon oxidation gives the acid 'B', this means that the acid must also have four carbon atoms.
(iii) Since the acid 'B' and alcohol 'C' have been formed as a result of hydrolysis of compound 'A', this means that the compound 'A' is an ester.
The sequence is given :
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