Question #d76ad

Question

2892 views around the world

You can reuse this answer
Creative Commons License

Answer 1 · 2015-08-12T19:33:48

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.