Basicity of t-butoxide vs ethoxide

  • #1

Main Question or Discussion Point

why is t-butoxide a stronger base than ethoxide?
 

Answers and Replies

  • #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?
 
  • #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.

..?
 
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  • #4
chemisttree
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Read up some more on the electronic effects of the methyl group.
 

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