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Basicity of t-butoxide vs ethoxide

  1. Nov 12, 2011 #1
    why is t-butoxide a stronger base than ethoxide?
     
  2. jcsd
  3. Nov 12, 2011 #2

    chemisttree

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    The difference between those two is the two extra methyls on the t-butoxide. Care to guess what methyl groups do to an adjacent charge?
     
  4. Nov 12, 2011 #3
    i honestly don't have a clue. the only thing relevant i can think of is that a more highly substituted carbon atom will form a more stable radical / carbocation. i'm not sure what this might imply in this situation, if anything.

    ..?
     
    Last edited: Nov 12, 2011
  5. Nov 12, 2011 #4

    chemisttree

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    Read up some more on the electronic effects of the methyl group.
     
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