AIIMS AIIMS Solved Paper-2015

  • question_answer
    \[[L\,\,{{T}^{-1}}{{Q}^{-1}}]\]What is the major product P in the above reaction?

    A) \[[M{{L}^{2}}\,\,{{T}^{-1}}{{Q}^{-2}}]\]

    B) \[\left[ \text{LT}{{\text{Q}}^{-\text{1}}} \right]\]

    C) \[{{O}_{1}}\]

    D) \[{{O}_{2}}\]

    Correct Answer: D

    Solution :

    \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-\underset{\begin{smallmatrix}  | \\  OH \end{smallmatrix}}{\mathop{CH}}\,-CH-C{{H}_{3}}\xrightarrow{{{H}^{+}}}\] \[C{{H}_{3}}C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-\underset{\begin{smallmatrix}  | \\  +\,\,OH \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}}\xrightarrow[-{{H}_{2}}O]{Slow\,\,step}\] \[C{{H}_{3}}C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  \underset{\begin{smallmatrix}  {{2}^{\circ }}\,carbocation \\  (less\,stable) \end{smallmatrix}}{\mathop{C{{H}_{3}}}}\, \end{smallmatrix}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-\underset{{}}{\mathop{\overset{+}{\mathop{C}}\,H}}\,-C{{H}_{3}}\]        \[\xrightarrow{1-2\,methyl\,shift}C{{H}_{3}}C{{H}_{2}}-\underset{+}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,-\underset{\begin{align}   & | \\  & C{{H}_{3}} \\  & {{3}^{\circ }}\,carbocation \\  & (more\,stable) \\ \end{align}}{\mathop{\overset{{}}{\mathop{C}}\,H}}\,-C{{H}_{3}}\]                 \[\xrightarrow[-{{H}^{+}}]{}C{{H}_{3}}.C{{H}_{2}}-\underset{{}}{\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}}\,=\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{\overset{{}}{\mathop{C}}\,H}}\,-C{{H}_{3}}\]                                 \[+C{{H}_{3}}C{{H}_{2}}-\underset{\begin{smallmatrix}  | \\  \underset{(\min or)}{\mathop{C{{H}_{3}}}}\, \end{smallmatrix}}{\overset{\begin{smallmatrix}  \overset{(major)}{\mathop{C{{H}_{3}}}}\, \\  | \end{smallmatrix}}{\mathop{C}}}\,=\underset{{}}{\mathop{\overset{{}}{\mathop{C}}\,H=}}\,C{{H}_{2}}\] When  the  formation  of an  alkene  is accompanied by 1, 2-shift, the reaction is called as retropinacol rearrangement. This rearrangement takes place it into an open chain compound and termed as Wagner rearrangement.


You need to login to perform this action.
You will be redirected in 3 sec spinner