AIIMS AIIMS Solved Paper-2007

  • question_answer
    The decreasing order of the stability of the ions \[C{{H}_{3}}-\underset{(I)}{\mathop{\overset{+}{\mathop{CH}}\,}}\,-C{{H}_{3}}\]          \[C{{H}_{3}}-\underset{(II)}{\mathop{\overset{+}{\mathop{CH}}\,}}\,-OC{{H}_{3}}\] \[C{{H}_{3}}-\underset{(III)}{\mathop{\overset{+}{\mathop{CH}}\,}}\,-COC{{H}_{3}}\]

    A)  \[\text{I}>II>III\]

    B)         \[III>II>I\]                         

    C)  \[II>III>I\]

    D)         \[II>I>III\]

    Correct Answer: D

    Solution :

    \[C{{H}_{3}}-\overset{+}{\mathop{CH}}\,-OC{{H}_{3}}\] is most stable due to resonance \[C{{H}_{3}}-\underset{(II)}{\mathop{\overset{+}{\mathop{CH}}\,-\underset{\centerdot \centerdot }{\overset{\centerdot \centerdot }{\mathop{O}}}\,-}}\,C{{H}_{3}}\overset{{}}{\longleftrightarrow}\]                                     \[C{{H}_{3}}-CH-\underset{\centerdot \centerdot }{\overset{+}{\mathop{O}}}\,-C{{H}_{3}}\] Carbocation \[C{{H}_{3}}-\overset{+}{\mathop{C}}\,H-COC{{H}_{3}}\] is least stable due to electron withdrawing nature of carbonyl group. Carbocation \[C{{H}_{3}}-\overset{+}{\mathop{C}}\,H-C{{H}_{3}}\]is less stable than \[C{{H}_{3}}-\overset{+}{\mathop{C}}\,H-OC{{H}_{3}}\] because it stabilised only by the \[+l\] effect of the two methyl groups. \[C{{H}_{3}}\to -\overset{+}{\mathop{CH}}\,-\leftarrow C{{H}_{3}}\] Therefore, correct order of decreasing stability is \[II>I>III\]


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