An organic compound (A) has molecular formula (C_(5)H_(10)O). It does not reduce Tollen's reagent but forms an orange precipitate with 2, 4-DNP reagent. It forms a carboxylic acid (B) with molecular formula (C_(3)H_(6)O_(2)) when treated with alkaline KMnO_(4), yellow precipitate on treatment with NaOH and I_(2) under vigorous conditions. On oxidation it gives ethanoic acid and propanoic acid. Sodium slat of (B) gave a hydrocarbon (C ) in Kolbe's ElectrolyticReduction. Identify (A), (B) and (C ) and write the reactions involved.

An organic compound (A) has molecular formula (C_(5)H_(10)O). It does

1.	An organic compound (A) has molecular formula (C_(5)H_(10)O). It does not reduce Tollen's reagent but forms an orange precipitate with 2, 4-DNP reagent. It forms a carboxylic acid (B) with molecular formula (C_(3)H_(6)O_(2)) when treated with alkaline KMnO_(4), yellow precipitate on treatment with NaOH and I_(2) under vigorous conditions. On oxidation it gives ethanoic acid and propanoic acid. Sodium slat of (B) gave a hydrocarbon (C ) in Kolbe's ElectrolyticReduction. Identify (A), (B) and (C ) and write the reactions involved.
Answer» Solution :The COMPOUND (A) is `CH_(3)CH_(2)COCH_(2)CH_(3)`. The reactions are EXPLAINED as under: `underset((A))(CH_(3)CH_(2)COCH_(2)CH_(3)) overset([O])to underset("Propanoic acid")(CH_(3)CH_(2)COOH)+underset("ETHANOIC acid")(CH_(3)COOH)` `underset("Sodium propionate")(CH_(3)CH_(2)COONa) underset("Electrolytic reduction")overset("Kolbe.s")to underset((C ))underset("n-Butane")(CH_(3)CH_(2)CH_(2)CH_(3))` Thus A, B, C are `A=CH_(3)CH_(2)COCH_(2)CH_(3)""B=CH_(3)CH_(2)COOH""C=CH_(3)CH_(2)CH_(2)CH_(3)`