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QUESTION

# Why is vinyl chloride is hydrolysed more slowly than ethyl chloride?

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.

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.