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An aliphatic unsaturated hydrocarbon (A)...

An aliphatic unsaturated hydrocarbon (A) when treated with `HgSO_(4)//H_(2)SO_(4)` yields a compound (B) having molecular formula `C_(3)H_(6)O`. (B) on oxidation with concentrated `HNO_(3)` gives two compounds ( C ) and (D). Compound (C ) when treated with `PCl_(5)` 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 `H_(2)SO_(4)`.
(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 phosphorus and name the reaction.

Text Solution

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(i) `(A) CH_(3)-C-=CH" "`(Propyne)
`(B) CH_(3)-overset(O)overset(||)C-CH_(3)" "`(Acetone)
`(C ) CH_(3)-COOH" "`(Acetic acid)
`(D) HCOOH" "` (Formic acid)
`(E ) CH_(3)COCl" "` (Acetylchloride)
`(F) CH_(3)COOC_(2)H_(5)" "`(Ethyl acetate)
(ii) `underset([C])underset(("Acetic acid"))(CH_(3)COOH) overset(Cl_(2),P)to underset((1))underset(Cl)underset(|)(CH_(2))COOH overset(Cl_(2),P)to`
`underset((2))(Cl_(2)CHCOOH)overset(Cl_(2),P)tounderset((3))(Cl_(3)C-COOH)`
`(1) rArr` monochloro acetic acid
`(2) rArr` dichloroacetic acid
`(3) rArr` trichloroacetic acid
This reaction is known as Hell Volhard Zelinsky reaction.
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