A) \[{{(C{{H}_{3}})}_{3}}C-Cl\]
B) \[C{{H}_{2}}=CHCl\]
C) \[C{{H}_{3}}C{{H}_{2}}Cl\]
D) \[C{{H}_{2}}=CHC{{H}_{2}}Cl\]
Correct Answer: B
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. \[C{{H}_{3}}=\underset{1}{\mathop{CH}}\,-\underset{\bullet \,\,\bullet }{\overset{\bullet \,\,\bullet }{\mathop{Cl_{\bullet }^{\bullet }}}}\,\underset{{}}{\overset{{}}{\longleftrightarrow}}\overset{\delta -}{\mathop{C{{H}_{2}}}}\,-\underset{II}{\mathop{CH}}\,=\overset{\delta +}{\mathop{Cl}}\,\] 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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