Uttarakhand PMT Uttarakhand PMT Solved Paper-2011

  • question_answer
    The major product of dehydration of\[{{(C{{H}_{3}})}_{3}}C-C{{H}_{2}}OH\]is

    A)  \[{{(C{{H}_{3}})}_{2}}C=CHC{{H}_{3}}\]

    B)  \[C{{H}_{3}}CH=CHC{{H}_{3}}\]

    C)  \[{{(C{{H}_{3}})}_{2}}CHCH=C{{H}_{2}}\]

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

    Correct Answer: A

    Solution :

     \[C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{2}}OH\xrightarrow[{}]{{}}C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,=CH-C{{H}_{3}}\] \[\underset{\begin{smallmatrix}  1{}^\circ carbonium\text{ }ion \\  \,\,\,(less\text{ }stable) \end{smallmatrix}}{\mathop{C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-\overset{+}{\mathop{C}}\,{{H}_{2}}}}\,\xrightarrow[{}]{1,2-methyl\text{ }shift}\] \[\underset{\begin{smallmatrix}  3{}^\circ carbonium\text{ }ion \\  \,\,\,\,(more\text{ }stable) \end{smallmatrix}}{\mathop{C{{H}_{3}}-\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{2}}-C{{H}_{3}}}}\,\] \[\downarrow -{{H}^{+}}\] \[C{{H}_{3}}-\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,=CH-C{{H}_{3}}\]


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