Question

Question #28777

Answer 1

This is an electronic effect rather than a steric effect.

Explanation:

Clearly, the shrubbery around the ipso carbon has REDUCED in the case of `H_2C=CHCl` as compared to say `H_3C-CH_2Cl` or even `H_3C-CH_2CH_2Cl`. And thus vinyl chloride might be faciley expected on these grounds to be a reactive substrate.

And so the stability of vinyl chloride should be traced to an electronic effect. As a chemist, as a physical scientist, you should look for data that supports this argument. These should be tabulated somewhere in your organic text, or in your physical chemistry text.

And if it is true that the `C-Cl` bond is stronger for a vinyl chloride, its activity in associative and dissociative mechanisms should be diminished.