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

Following step can be adopted to get the structure A, B and C.
(a) Ester produces a carboxylic acid and alcohol on hydrolysis.
(b) Ester A has 8 carbon atoms, calculate number of C atoms in acid and alcohol.
( c ) Guess the alcohol and acid according to the given reactions.
(d) Now guess the ester.
( e ) Write all the related equations.
Compound C on dehydration gives but-1-ene
`(CH_(3)CH_(2)CH=CH_(2))`, so it must be butan-1-ol.
When subjected to oxidation C gives butanoic acid B. Thus, compound A is
`CH_(3)CH_(2)CH_(2)COOCH_(2)CH_(2)CH_(2)CH_(3)`.
The reactions involved are as follows:
`underset((A))(CH_(3)CH_(2)CH_(2)COOCH_(2)CH_(2)CH_(2)CH_(3)) overset(H_(2)O //H^(+))to `
`underset((B))(CH_(3)CH_(2)CH_(2)COOH) +underset((C )) (CH_(3)CH_(2)CH_(2)CH_(2)OH)`
`underset((C )) (CH_(3)CH_(2)CH_(2)CH_(2)OH) overset(CrO_(3))to underset((B))(CH_(3)CH_(2)CH_(2)COOH)`
`CH_(3)CH_(2)CH_(2) underset((C ))(CH_(2)) OH underset(H_(2)SO_(4)) overset("Conc.")to underset("But-1-ene")(CH_(3)CH_(2)CH=CH_(2))`