Manipal Medical Manipal Medical Solved Paper-2010

  • question_answer
    The\[{{S}_{N}}1\]reactivity of the following halides will be in the order
    (i) \[{{(C{{H}_{3}})}_{3}}CBr\]
    (ii) \[{{({{C}_{6}}{{H}_{5}})}_{2}}CHBr\]
    (iii) \[{{({{C}_{6}}{{H}_{5}})}_{2}}C(C{{H}_{3}})Br\]
    (iv) \[{{(C{{H}_{3}})}_{2}}CHBr\]
    (v) \[{{C}_{2}}{{H}_{5}}Br\]

    A)  (ii)> (i) > (iii) > (v) > (iv)

    B)  (i)>(m)>(v)>(ii)>(iv)

    C)  (v)> (i)> (ii) > (iv) > (iii)

    D)  (iii)> (ii)> (i) > (iv) > (v)

    Correct Answer: D

    Solution :

     In\[{{S}_{N}}1\](Unimolecular nucleophilic substitution) reactions, Rate \[\propto \] [substrate] Rate determining step is the formation of carbocation and depends on the stability of carbocation   formed.   The   stability   of carbocations follow the order \[{{({{C}_{6}}{{H}_{5}})}_{2}}{{C}^{+}}(C{{H}_{3}})>{{({{C}_{6}}{{H}_{5}})}_{2}}\overset{+}{\mathop{C}}\,H>{{(C{{H}_{3}})}_{3}}{{C}^{+}}\]         \[{{(C{{H}_{3}})}_{2}}\overset{+}{\mathop{C}}\,H>C{{H}_{3}}CH_{2}^{+}\] Thus, the order of reactivity towards\[{{S}_{N}}1\] reaction is (iii) > (ii) > (i) > (iv) > (v)


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