Question

An organic compound ‘A’ with molecular formula C₅H₈O₂ is reduced to n-pentane with hydrazine followed by heating with NaOH and Glycol. ‘A’ forms a dioxime with hydroxylamine and gives a positive Iodoform and Tollen’s test. Identify ‘A’ and give its reaction for Iodoform and Tollen’s test.

Answer 1

DBE for the given compound with molecular formula C₅H₈O₂ will be 2 as per the following formula.

DBE (Double bond equivalent) \(= C- \frac{H}{2} + 1 = 5 - \frac{8}{2} +1 = 2\)

Since DBE of the given compound is 2, it will have either two double bonds or one triple bond.

Now, the given compound is reduced to n-pentane with hydrazine followed by heating with NaOH and Glycol, it means it is having carbonyl group.

Also the given compound forms a dioxime with hydroxyl amine, it will have two carbonyl group.

Since the compound gives positive iodoform test and tollen’s test, it must have one keto group and another aldehyde group.

The given compound should have the structure