Manipal Engineering Manipal Engineering Solved Paper-2008

  • question_answer
    Which reaction intermediate is formed during the condensation reaction between acetaldehyde and formaldehyde?

    A) \[:C{{H}_{2}}CHO\]

    B)                        \[\overset{+}{\mathop{C}}\,{{H}_{2}}CHO\]

    C) \[\overset{+}{\mathop{C}}\,{{H}_{2}}OH\]         

    D)        \[:\bar{C}HCHO\]

    Correct Answer: A

    Solution :

    The \[\alpha \]-hydrogen atoms of acetaldehyde due to \[-E\]effect of\[\rangle C=O\]group is slightly acidic in nature. In crossed aldol condensation between formaldehyde and acetaldehyde, in the first step\[O{{H}^{-}}\]ion (from the base added) abstracts one of these acidic a-hydrogen to form carbaplion or enolate ion which is stabilized by resonance. \[H{{O}^{-}}+H-C{{H}_{2}}-\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-H\overset{Slow}{\mathop{\rightleftharpoons }}\,\] \[{{H}_{2}}O+_{\bullet }^{\bullet }C{{H}_{2}}-\overset{\begin{smallmatrix}  O \\  || \end{smallmatrix}}{\mathop{C}}\,-H\]


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