RAJASTHAN PMT Rajasthan - PMT Solved Paper-2008

  • 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 the above

    Correct Answer: A

    Solution :

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


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