CEE Kerala Engineering CEE Kerala Engineering Solved Paper-2007

  • 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)  (v)>(iv)>(i)>(ii)>(iii)

    B)  (ii)>(i)>(iii)>(v)>(iv)

    C)  (i)>(iii)>(v)>(ii)>(iv)

    D)  (v)>(i)>(ii)>(iv)>(iii)

    E)  (iii)>(ii)>(i)>(iv)>(v)

    Correct Answer: E

    Solution :

    \[{{S}_{N}}1\] (Unimolecular nucleophilic substitution reactions) \[Rate\propto (substrate)\] Rate of determining step in the formation of carbocation depends on the stability of carbocation formed.  The stability of carbocations follow the order- \[{{({{C}_{6}}{{H}_{5}})}_{2}}{{C}^{+}}(C{{H}_{3}})>{{({{C}_{6}}{{H}_{5}})}_{2}}\overset{+}{\mathop{C}}\,H>\]                         \[{{(C{{H}_{3}})}_{2}}\overset{+}{\mathop{C}}\,H>C{{H}_{3}}CH_{2}^{+}\] \[\because \]Order of\[{{S}_{N}}1\]reactivity is \[{{({{C}_{6}}{{H}_{5}})}_{2}}C(C{{H}_{3}})Br>{{({{C}_{6}}{{H}_{5}})}_{2}}CHBr>\] \[{{(C{{H}_{3}})}_{3}}CBr>{{(C{{H}_{3}})}_{2}}\overset{+}{\mathop{C}}\,HBr>{{C}_{2}}{{H}_{5}}Br\] ie,           \[iii>ii>i>iv>v\]


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