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) Since the compound A on hydrolysis with dilute `H_2SO_4` gives an acid (B) and an alcohol (C), it must be an ester.
(ii) Since the oxidation of alcohol (C) gives the acid (B), therefore, both the carboxylic acid (B) and alcohol (C) must contain same number of carbon atoms.
(iii) Further, since ester A contains eight carbon atoms, both carboxylic acid (B) and alcohol (C) must contain four carbon atoms each.
(iv) Since alcohol (C) on dehydration gives but-1-ene, therefore, it must be a straight chain alcohol, i.e., butan-1-ol.
(v) Since (B) is obtained by the oxidation of alcohol (C), therefore, it must be butanoic acid.
(vi) Since ester (A) on hydrolysis gives butan-1-ol and butanoic acid, it must be butyl butanoate.
(vii) The relavant equations for all the reactions involved may be explained as follows: