CMC Medical CMC-Medical VELLORE Solved Paper-2012

  • question_answer
    Which of the following is least reactive in a nucleophilic substitution reaction?

    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. 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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