Chhattisgarh PMT Chhattisgarh 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. \[\underset{t-butyl\,chloride}{\mathop{{{H}_{3}}C-\underset{C{{H}_{3}}}{\mathop{\underset{|}{\mathop{\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,}}\,}}\,-Cl}}\,\xrightarrow[-Cl]{slow}\underset{(most\,stable)}{\mathop{\underset{{{3}^{o}}\,\,carbocation}{\mathop{{{({{H}_{3}}C)}_{3}}{{C}^{+}}}}\,}}\,\xrightarrow[fast]{+O{{H}^{-}}}\underset{t-butyl\,alcohol}{\mathop{{{({{H}_{3}}C)}_{3}}COH}}\,\]


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