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  4. Which of the following is least reactive in a nucleophilic substitution reaction?

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Q. Which of the following is least reactive in a nucleophilic substitution reaction?

AIPMTAIPMT 2004Haloalkanes and Haloarenes

Solution:

Chlorine of vinyl chloride $(CH_2=CHCI)$ is non-reactive (less reactive) towards nucleophile (in nucleophilic substitution reaction) because it shows the following resonating structure due to $+M$ effect of $- Cl$ atom.
In structure II, $Cl$-atom have positive charge and partial double bond character with $C$ of vinyl group,so it is more tightly attracted towards the nucleus and it does not get replaced by nucleophile in $S_N$ reaction.

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