Question

An organic compound (A) (molecular formula C₈H₁₆O₂) 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 C₈H₁₆O₂ 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 C₈H₁₆O₂ is butylbutanoate.