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

(a) since the given compound on hydrolysis with dil , `H_2 SO_4` gives carboxlic acid (B ) and an alcohol (C ) , it must be an ester .
(b) since the oxidation of alcohol (C ) gives the acid B, therefore both the carboxylic acid B and alcohol C must contain same number of C atoms
(c ) since ester (A ) contain 8 carbon atoms , therefore , both carboxylic acid (B ) and the alcohol (C ) must contain 4 C atoms eac h.
(d ) alcohol (C ) in dehydration gives but -1- ene and therefore c ,must be straight chain alcohol i.e., butan -1-ol .
(e ) (B ) is obtained by the oxidation of (C ) and therefore , B must be butanoic acid .
this also suggests that the ester (A ) must be butyl butanoate , the relevant reaction are :
`underset((M.FC_5 C_8 H_16 ) O_2)underset(" Butyl butanoate "(A ))(CH_3 CH_2 overset(O) overset(||) C-OCH_2 CH_2CH_3 ) underset( "Hydrogen ") overset(d i l H_2 SO_4)to underset( "butanoic acid (B ) ") (CH_3 CH_2CH_2overset(O ) overset(|| )C-OH )+ underset("butanol (C )") (CH_3 CH_2CH_2CH_2OH)`
` underset("Butanoic acid (B )")(CH_3 CH_2 CH_2COOH ) underset("Oxidation ") overset(CrO_3 //CH_3COOH) larr underset( "Butanol(C )")(CH_3CH_2 CH_2 CH_2 OH) overset("Dehydration ") to underset("But-1-ene ") (CH_3 CH_2CH=CH_2)`