RAJASTHAN ­ PET Rajasthan PET Solved Paper-2005

  • question_answer
    Which of the following alcohol will form the most stable carbonium ion on dehydration?

    A)  \[C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{2}}OH\]

    B)  \[C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,}}\,-OH\]

    C)  \[C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  OH \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{2}}C{{H}_{3}}\]

    D)  \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}OH\]

    Correct Answer: B

    Solution :

     Tertiary alcohol forms the most stable carbonium ion (tertiary carbonium ion) on dehydration \[C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-OH\xrightarrow[{}]{Dehvdration}\underset{\begin{smallmatrix}  tertiary\text{ }carbonium \\  \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,ion \end{smallmatrix}}{\mathop{C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{{{C}^{+}}}}}\,}}\,\] \[\xrightarrow[{}]{{}}\underset{\begin{smallmatrix}  2-methyl \\  propene \end{smallmatrix}}{\mathop{C{{H}_{3}}-\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,=C{{H}_{2}}}}\,\]


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