Why Is t-Butoxide a Stronger Base Than Ethoxide?

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t-Butoxide is a stronger base than ethoxide primarily due to the presence of two additional methyl groups. These methyl groups influence the stability of the adjacent charge through electronic effects. The increased steric hindrance and hyperconjugation from the methyl groups stabilize the negative charge on the t-butoxide ion, making it a more effective base. This stabilization is linked to the ability of highly substituted carbon atoms to form more stable radicals or carbocations, which may enhance the basicity of t-butoxide compared to ethoxide. Understanding the electronic effects of methyl groups is crucial in analyzing their impact on 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.

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

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