Why vinyl chloride does not go nucleophilic substitution?
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Vinyl chloride (CH2=CHCl) is unreactive in nucleophilic substitution reaction due to resonance. In vinyl chloride, the lone pair of electrons on chlorine is in resonance with the C-C double bond, because of which there is partial double bond character in C-Cl bond.
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Explanation:
As a result of resonance, the carbon-chloride bond acquires some double bond character. Hence, vinyl chloride does not undergo nucleophillic substitution reactions.
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