compare the reactivity of vinyl halide and alkyl halide towards nucleophilic substitution reaction.
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vinyl halide is more reactive towards nucleophilic reaction because of resonance
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Alkyl halides are more reactive toward nucleophilic substitution reactions when compared to vinyl halides.
- The term Vinyl halides indicate the group , where is a halide.
- Alkyl halides have a general formula, .
- Nucleophilic substitution reactions involve the replacement of the halide with another nucleophile.
- The bond between carbon and the halide must be broken, leaving the carbon with a net positive charge. The easier the bond cleavage, the easier the attack of the incoming nucleophile.
- The carbon must be electron deficient for the attack of nucleophiles.
- In vinyl halides, there is a double bond between the two carbon atoms. As the halide is electron-withdrawing in nature, it attracts the π-electrons of the double bond, resulting in resonance.
- Due to resonance, there will be a partial double bond between chlorine and carbon, which makes the bond cleavage difficult.
- Also, the π-electrons of the double bond decrease the positive charge on the carbon.
- Hence, the vinyl halides are less reactive than alkyl halides towards nucleophilic substitution reactions.
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