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.

Explanation

(i) The available data shows that the compound [A] upon hydrolysis give a carboxylic acid [B] and an alcohol [C]. It must be an ester.
(ii) Since the alcohol [C] upon oxidation with chromic acid gave back the carboxylic acid [B]. Both the acid and alcohol must have the same number of carbon atoms (four each).
(iii) The alcohol [C] upon dehydration gave an alkene.
The equations for the reactions are given :
`underset((C_(8)H_(16)O_(2)))underset("Butylbutanoate[A]")(CH_(3)CH_(2)CH_(2)COOCH_(2)CH_(2)CH_(2)CH_(3))overset(H_(2)O"/"H^(+))rarrunderset("Butanoic acid [B]")(CH_(3)CH_(2)CH_(2)COOH)+underset("Butan-1-01[C]")(CH_(3)CH_(2)CH_(2)CH_(2)OH`
`underset("Butanoic acid [B]")underset()(CH_(3)CH_(2)CH_(2)COOH)overset(H_(2)CrO_(4))underset("oxidation")larrunderset("Butan-1-01[C]")underset()(CH_(3)CH_(2)CH_(2)CH_(2)OH)overset("Dehydration")underset(-H_(2)O)rarrunderset("But-1-ene")underset()(CH_(3)CH_(2)CH=CH_(2)`