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Question -

An organic compound (A) (molecular formula C8H16O2)was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and analcohol 



Answer -

(C). Oxidation of (C) with chromic acid produced (B). (C) on dehydration gives but-1-ene.Write equations for the reactions involved.


Answer

An organic compound A with molecular formulaC8H16O2 gives a carboxylic acid (B) and an alcohol (C) onhydrolysis 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 Cmust contain equal number of carbon atoms.

Since compound A contains a total of 8 carbon atoms, eachof 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, acidB is butanoic acid.

Hence, the ester with molecular formula C8H16O2 isbutylbutanoate.

All the given reactions can be explained by the followingequations.

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