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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?

ManipalManipal 2007Haloalkanes and Haloarenes

Solution:

Chlorine of vinyl chloride $ (C{{H}_{2}}=CHCl) $ 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.
image
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.