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Vinyl chloride is hydrolyzed more slowly than ethyl chloride because the ##”C-Cl”## bond in vinyl chloride has some double bond character.
There are two reasons for the slow hydrolysis of vinyl chloride.
(a) The carbon atom in vinyl chloride is ##”sp”^2## hybridized.
The ##”C-Cl”## bond contains more s character from the ##”C”## atom, so the bond is “tighter” and more difficult to break.
(b) The ##”C-Cl”## bond in vinyl chloride has some double bond character.
Vinyl chloride is a hybrid of two resonance structures.
The second structure is a minor contributor but, to the extent that it occurs, it gives some double bond character to the ##”C-Cl”## bond.
In ethyl chloride the ##”C-Cl”## bond is a pure single bond.
Thus, vinyl chloride undergoes hydrolysis more slowly than ethyl chloride.
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