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 organic compound (S) with M.F. `C_(8)H_(16)O_(2)` upon hydrolysis with dil. `H_(2)SO_($)` gives carboxylic acid (B) and the alcohol (C), therefore, (A) must be an ester. Further, since oxidation of (C) with chromic acid produces the acid (B), therefore, both the carboxylic acid (B) and the alcohol (C) must contains the same number of carbon atoms.
(ii) Since ester (A) contains eight carbon atoms, therefore, both the carboxylic acid (B) and the alcohol (C) must contain four carbon atoms each.
(iii) Since the alcohol (C) on dehydration gives but-1-ene, therefore, (C) must be a straight chain alcohol, i.e., butna-1-ol.
(iv) if (C) is butan-1-ol, then the acid (B) which it gives on oxidation must be butanoic acid and the ester (A) must be butyl butanoate.
(v) The relevant equation for the all the reactions involved may be explained as follows:
`underset("Butyl butanoate (A) "(M.F.=C_(8)H_(16)O_(2)))(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)(C)-OCH_(2)CH_(2)CH_(2)CH_(3) underset("Hydrolysis")overset("Dil. "H_(2)SO_(4))to underset("Butanoic acid (B)")(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)(C)-OH)+underset("Butan-1-ol (C)")(CH_(3)CH_(2)CH_(2)CH_(2)OH)`
`underset("Butanoic acid (B)")(CH_(3)CH_(2)CH_(2)-overset(O)overset(||)(C)-OH) underset("Oxidation")overset(CrO_(3)//H_(2)SO_(4))larr underset("Butan-1-ol (C)")(CH_(3)CH_(2)CH_(2)CH_(2)OH) underset((-H_(2)O)) overset('Dehydration")tounderset("But-2-ene")(CH_(3)CH=CHCH_(3))`.