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Why is the chlorine atom in vinyl chloride comparatively less reactive?

1. Because the carbon attached to chlorine is sp³-hybridised and therefore more acidic than an sp²-hybridised carbon
2. Because the C–Cl bond acquires some partial double-bond character
3. Because resonance is involved
4. All of the above

Correct answer: Because the C–Cl bond acquires some partial double-bond character

Solution

In vinyl chloride the chlorine lone pair delocalises into the C=C, giving the C-Cl bond partial double-bond character (shorter, stronger, less reactive). The stored 'sp3 carbon' reason is wrong - the carbon is sp2.

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