1. Nov 12, 2011 #1

   newyorkcity

   

   why is t-butoxide a stronger base than ethoxide?

    

   newyorkcity, Nov 12, 2011
2. 
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3. Nov 12, 2011 #2

   chemisttree

   

   Science Advisor

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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?

    

   chemisttree, Nov 12, 2011
4. Nov 12, 2011 #3

   newyorkcity

   

   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

   newyorkcity, 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.

    

   chemisttree, Nov 12, 2011

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