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Resonance Stabilization when electrons can't donate?

  1. Jun 21, 2011 #1
    A question in ExamKrackers asks us why triphenylmethanol is so acidic. Link to the structure below:

    http://en.wikipedia.org/wiki/Triphenylmethanol

    Explanation:

    I'm not seeing how the lone pairs on the Oxygen could donate into any of the rings though. It can't donate those electrons onto the carbon it's next to or else that carbon would have 5 bonds.

    Can someone explain? Thanks!
     
  2. jcsd
  3. Jun 21, 2011 #2

    SpectraCat

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    Science Advisor

    You are right (again) ... that explanation is simply wrong. In fact, the wikipedia link directly contradicts it, citing precisely the answer you give (i.e. no resonance stabilization since the central C atom is saturated). In fact, the opposite effect (i.e. increased basicity) is expected, since the carbocation formed by elimination of water from the protonated form *IS* highly resonance stabilized.
     
  4. Jun 21, 2011 #3
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