An organic compound (A) gives violet colour with neutral \(\mathrm{FeCl}_{3}\). It answers Liebermann's test. This compound on catalytic reduction gives (B). The saturated compound (B) on oxidation with \(\mathrm{CrO}_{3}\) gives (C) of molecular formula \(\mathrm{C}_{6} \mathrm{H}_{10} \mathrm{O}\). (C) gives precipitate with 2,4 -dinitrophenylhydrazine. (C) can be obtained by reductive ozonolysis of (D). The other product of reductive ozonolysis, (E), undergoes Cannizzaro reaction with benzaldehyde to give (F) and HCOONa. Answer the following questions. (D) can be obtained by heating the amine oxide formed from

Compound (A) gives violet color with neutral FeCl3, which is a test for phenols. It is also positive for Liebermann's test, which confirms the presence of a phenolic hydroxyl group. Hence, the compound (A) is a phenol derivative.

Phenolic compounds, upon catalytic reduction, lose their hydroxyl group and become saturated hydrocarbons. So, compound (B) is a saturated hydrocarbon derived from compound (A).

Compound (C) has a molecular formula of \(\textnormal{C}_{6}\textnormal{H}_{10}\textnormal{O}\) and gives precipitate with 2,4-dinitrophenylhydrazine, which indicates that the compound (C) is a carbonyl compound. Based on the molecular formula and the presence of carbonyl group, compound (C) can be identified as hexan-3-one.

Compound (D) can be obtained by heating the amine oxide formed. It's given that compound (C) can be obtained by reductive ozonolysis of compound (D). The ozonolysis of an alkene results in the conversion of the double bond into carbonyl groups. Therefore, compound (D) should be an alkene. Since compound (C) can be formed (hexan-3-one), compound (D) should be hex-3-ene. When hex-3-ene undergoes reductive ozonolysis, compounds (C) and (E) are formed.

Compound (E) undergoes the Cannizzaro reaction with benzaldehyde to give compound (F) and HCOONa (sodium formate). The Cannizzaro reaction occurs between two aldehydes, one without an alpha-hydrogen and one with an alpha-hydrogen. In this case, benzaldehyde reacts with compound (E) to produce compound (F) and HCOONa. As benzaldehyde doesn't have an alpha-hydrogen, compound (E) should be an aldehyde with an alpha-hydrogen. Based on the reductive ozonolysis, compound (E) is propanal. Compound (F), produced after the Cannizzaro reaction, would be the reduction product of benzaldehyde. Thus, compound (F) is benzyl alcohol. Now we have found the compounds (A) to (F) as follows: (A) is a phenol derivative (B) is a saturated hydrocarbon derived from (A) (C) is hexan-3-one (D) is hex-3-ene (E) is propanal (F) is benzyl alcohol