Question

An organic compound(A)(molecular formula$C_8H_{16}O_2$)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.

Answer 1

An organic compound A with molecular formula $C_8H_{16}O_2$ gives a carboxylic acid(B)and an alcohol(C)on hydrolysis with dilute sulphuric acid.Thus,compound A must be an ester.Further, alcohol C gives acid B on oxidation with chromic acid.Thus,B and C must contain equal number of carbon atoms.
Since compound A contains a total of 8 carbon atoms,each of B and C contain 4 carbon atoms.
Again,on dehydration,alcohol C gives $but-1-ene$.Therefore,C is of straight chain and hence,it is $butan-1-ol$.

On oxidation,$Butan-1-ol$ gives butanoic acid.

Hence, acid B is butanoic acid.Hence,the ester with molecular formula $C_8H_{16}O_2$2 is butylbutanoate.

All the given reactions can be explained by the following equations.