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 also produced B. On dehydration C gives but-1-ene. Write the equations for the reactions involved.

Explanation

(i) Since, A produces carboxylic acid B and an alcohol C on hydrolysis, hence compound A is an ester.
(ii) Alcohol C on oxidation produces acid B. It means both B and C have same number of carbon atoms, i.e. four each as C on dehydration gives but-2-ene.
`underset("Butyl butanoate (A)")(CH_(3)CH_(2)CH_(2)-oversetoverset(O)(||)(C)-OCH_(2)CH_(2)CH_(2)CH_(3))`
`underset(("Hydrolysis"))overset("Dil."H_(2)SO_(4))rarrundersetunderset(("B"))("Butanoic acid")(CH_(3)CH_(2)CH_(2)COOH)`
`undersetunderset("(C)")("Butan-1-ol")(+CH_(3)CH_(2)CH_(2)CH_(2)OH)undersetunderset(("Oxidation"))("Chromic acid")overset([O])rarrundersetunderset("(B)")("Butanoic acid")(CH_(3)CH_(2)CH_(2)COOH)`
`underset("Dehydration"(-H_(2)O))overset("Conc."H_(2)SO_(4))rarrunderset("But-2-ene")(CH_(3)CH=CHCH_(3))`