Question

Question #d76ad

Answer 1

Vinyl chloride is hydrolyzed more slowly than ethyl chloride because the `"C-Cl"` bond in vinyl chloride has some double bond character.

Explanation:

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.

(from www.askiitians.com)

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.