A) \[{{(C{{H}_{3}})}_{3}}C-Cl\]
B) \[\text{C}{{\text{H}}_{\text{2}}}=\,\,\text{CHC1}\]
C) \[\text{C}{{\text{H}}_{3}}\,\text{C}{{\text{H}}_{2}}\text{C1}\]
D) \[\text{C}{{\text{H}}_{\text{2}}}=\text{CHC}{{\text{H}}_{\text{2}}}\text{C1}\]
Correct Answer: B
Solution :
Chlorine of vinyl chloride \[(C{{H}_{3}}=CHCl)\] is non-reactive (less reactive) towards nucleophile in nucleophilic substitution reaction because it shows the following resonating structure due to +M effect of \[\text{Cl}\] atom. \[\text{CH2}=\underset{1}{\mathop{\text{CH}}}\,\underset{..}{\mathop{\overset{..}{\mathop{\text{C1}}}\,}}\,:\text{ }\underset{{}}{\overset{{}}{\longleftrightarrow}}\overset{\delta -}{\mathop{\text{C}{{\text{H}}_{\text{2}}}}}\,\underset{\mathbf{|}\,\mathbf{|}}{\mathop{\text{CH}}}\,=\overset{\delta +}{\mathop{\text{C1}}}\,\] In structure II, \[\text{Cl}\]-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 \[{{\text{S}}_{{{N}^{-}}}}\] reaction.
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