NEET NEET SOLVED PAPER 2013

  • question_answer
    The order of stability of the following tatutomeric compound is \[\underset{\text{I}}{\mathop{\text{CH}{{  }_{\text{2}}}\text{=}\overset{\begin{smallmatrix}  \text{OH} \\  \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{-C}{{\text{H}}_{\text{2}}}\text{-CH}{{  }_{\text{2}}}-\overset{\begin{smallmatrix}  \text{OH} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{-C}{{\text{H}}_{3}}}}\,\]\[\underset{\text{II}}{\mathop{\text{CH}{{  }_{3}}\text{=}\overset{\begin{smallmatrix}  \text{OH} \\  \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{-C}{{\text{H}}_{\text{2}}}-\overset{\begin{smallmatrix}  \text{OH} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{-C}{{\text{H}}_{3}}}}\,\]\[\underset{\text{III}}{\mathop{\text{C}{{\text{H}}_{\text{3}}}\text{-}\overset{\begin{smallmatrix}  \text{OH} \\  \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{=CH-}\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{-C}{{\text{H}}_{\text{3}}}}}\,\]

    A) \[I>II>III\]

    B) \[III>II>I\]

    C) \[II>I>III\]

    D) \[II>III>I\]

    Correct Answer: B

    Solution :

    The rolls of \[\text{ }\!\!\beta\!\!\text{ -}\]dicarbonyl compounds are more stable because of conjugation and intermolecular H-bonding. Thus, the order of stability is \[\underset{\text{III}}{\mathop{\underset{\begin{smallmatrix}  \text{(Stabilised}\,\text{by}\,\text{conjugation} \\  \text{and}\,\text{H-bonding)} \end{smallmatrix}}{\mathop{{{\text{H}}_{\text{3}}}\text{C}-\overset{\begin{smallmatrix}  \text{OH} \\  \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,\text{=}\,\text{CH}-\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\text{C}{{\text{H}}_{\text{3}}}}}\,}}\,\]\[\text{}\,\text{C}{{\text{H}}_{\text{3}}}-\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\underset{\text{II}}{\mathop{\text{C}{{\text{H}}_{\text{2}}}}}\,-\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\text{C}{{\text{H}}_{\text{3}}}\]\[\underset{\text{I}}{\mathop{\underset{\begin{smallmatrix}  \text{Less}\,\text{Stable}\,\text{as}\,\text{(=)bond} \\  \text{is}\,\text{not}\,\text{in}\,\text{conjugation}\,\text{with}\,\text{carbonyl}\,\text{group} \end{smallmatrix}}{\mathop{\text{}\,\text{C}{{\text{H}}_{\text{3}}}=\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\text{C}{{\text{H}}_{\text{2}}}-\overset{\begin{smallmatrix}  \text{O} \\  \text{ }\!\!|\!\!\text{  }\!\!|\!\!\text{ } \end{smallmatrix}}{\mathop{\text{C}}}\,-\text{C}{{\text{H}}_{\text{3}}}}}\,}}\,\]


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