Question

An aliphatic unsaturated hydrocarbon $\left(A\right)$ when treated with $HgS{O}_4/H_{2}S{O}_4$ yields a compound $\left(B\right)$ having molecular formula $C_3{H}_{6}O$. $\left(B\right)$ on oxidation with concentrated $HN{O}_3$ gives two compounds $\left(C\right)$ and $\left(D\right)$. Compound $\left(C\right)$ when treated with $P{Cl}_5$ gives compound $\left(E\right)$. $\left(E\right)$ when reacts with ethanol gives a sweet smelling liquid $\left(F\right)$. Compound $\left(F\right)$ is also formed when $\left(C\right)$ reacts with ethanol in the presence of concentrated $H_{2}S{O}_4$.
(i) Identify the compound $A,B,C,D,E$ and $F$.
(ii) Give the chemical equation for the reaction of $\left(C\right)$ with chlorine in the presence of red phosphorous and name the reaction.

Answer 1

The hydration of propyne with $HgS{O}_4/H_{2}S{O}_4$ followed by keto enol tautomerism gives propan-2-one. Oxidation with concentrated nitric acid gives a mixture of acetic acid and formic acid. Acetic acid reacts with $PC{l}_5$ to form acetyl chloride.
Acetyl chloride undergoes esterification with ethanol to form ethyl acetate. Ethyl acetate is also formed when acetic acid reacts with ethanol in presence of conc. $H_{2}S{O}_4$.
In Hell Volhard- Zelinsky (HVZ) reaction, acetic acid reacts with $C{l}_2/$ red P to form monochloro acetic acid. Further chlorination gives dichloro acetic acid and trichloro acetic acid.