Question

An aliphatic unsaturated hydrocarbon (A) when treated with HgSO₄/H₂SO₄ yields a compound (B) having molecular formula C₃H₆O. (B) on oxidation with concentrated HNO₃ gives two compounds (C) and (D). Compound (C) when treated with PCl5 gives compound (E). (E) when reacts with ethanol gives a sweet smelling liquid (F). Compound (F) is also formed when (C) reacts with ethanol in the presence of concentrated H2SO4.

(i) Identify the compound A,B,C,D,E and F.
(ii) Give the chemical equation for the reaction of (C) with chlorine in the presence of red phosphorous and name the reaction.

Answer 1

Compound A is propene, which forms propanol (B) when treated with HgSO4/H2SO4, and upon further oxidation produces acetic acid (C) and formaldehyde (D). Acetic acid turns into acetyl chloride (E) with PCl5, which yields ethyl acetate (F) upon reaction with ethanol. Acetic acid reacts with chlorine in the presence of red phosphorous in a halogenation reaction.

Step-by-step explanation:

The compound A is most likely propene (C₃H₆), an aliphatic unsaturated hydrocarbon. When treated with HgSO₄/H₂SO₄, it will hydrate to form propanol (B), with the molecular formula C₃H₆O. Upon oxidation with concentrated HNO₃, propanol can yield acetic acid (C) and formaldehyde (D).

Acetic acid when treated with PCl5 turns into acetyl chloride (E). This acetyl chloride, upon reaction with ethanol, will form ethyl acetate (F), a sweet-smelling liquid. Ethyl acetate is also formed when acetic acid (C) reacts with ethanol in the presence of concentrated H₂SO₄.

For part (ii) of the question, the chemical equation for the reaction of acetic acid (C) with chlorine in the presence of red phosphorous can be represented as: C₂H₄O₂ + Cl₂ → C₂H₃ClO₂ + HCl. This reaction is known as halogenation.