JIPMER Jipmer Medical Solved Paper-2009

  • question_answer
    t-butyl chloride preferably undergo hydrolysis by

    A)  \[{{S}_{N}}\] 1 mechanism

    B)  \[{{S}_{N}}\] 2 mechanism

    C)  Any of (a) and (b)

    D)  None of these

    Correct Answer: A

    Solution :

    Tertiary halide preferentially undergo \[{{S}_{N}}\]1 substitution as they can give stable carbocation. \[\underset{t\text{-}butyl\,chloride}{\mathop{{{H}_{3}}C-\underset{C{{H}_{3}}}{\overset{C{{H}_{3}}}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}\,}}}\,-Cl}}\,\xrightarrow[-Cl]{slow}\underset{\begin{smallmatrix}  3{}^\circ \,carbocation \\  \,\,(most\,stable) \end{smallmatrix}}{\mathop{{{({{H}_{3}}C)}_{3}}{{C}^{+}}}}\,\xrightarrow[fast]{+O{{H}^{-}}}\] \[\underset{t\text{-}butyl\,alcohol}{\mathop{{{({{H}_{3}}C)}_{3}}COH}}\,\]


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