Why Is t-Butoxide a Stronger Base Than Ethoxide?

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Discussion Overview

The discussion centers around the comparative basicity of t-butoxide and ethoxide, exploring the reasons behind the strength of t-butoxide as a base. The scope includes theoretical considerations and electronic effects related to molecular structure.

Discussion Character

  • Exploratory, Technical explanation, Conceptual clarification

Main Points Raised

  • One participant notes that the difference in basicity is attributed to the two additional methyl groups on t-butoxide and prompts others to consider the impact of these groups on an adjacent charge.
  • Another participant expresses uncertainty, suggesting that more highly substituted carbon atoms may form more stable radicals or carbocations, but is unsure of its relevance to the discussion on basicity.
  • A later reply encourages further reading on the electronic effects of the methyl group, implying that these effects are significant in understanding the basicity difference.

Areas of Agreement / Disagreement

The discussion does not reach a consensus, as participants express differing levels of understanding and uncertainty regarding the implications of molecular structure on basicity.

Contextual Notes

Limitations include potential missing assumptions about the role of sterics and electronic effects, as well as unresolved connections between stability of intermediates and basicity.

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why is t-butoxide a stronger base than ethoxide?
 
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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?
 
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:
Read up some more on the electronic effects of the methyl group.
 

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