Why Is t-Butoxide a Stronger Base Than Ethoxide?

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SUMMARY

t-Butoxide is a stronger base than ethoxide primarily due to the presence of two additional methyl groups that stabilize the negative charge through hyperconjugation and inductive effects. The increased steric hindrance from these methyl groups also contributes to the stability of the t-butoxide ion compared to ethoxide. Understanding these electronic effects is crucial for predicting the behavior of these bases in chemical reactions.

PREREQUISITES
  • Understanding of acid-base chemistry
  • Familiarity with organic chemistry concepts such as carbocation stability
  • Knowledge of hyperconjugation and inductive effects
  • Basic grasp of molecular structure and sterics
NEXT STEPS
  • Research the electronic effects of methyl groups in organic compounds
  • Study the stability of carbocations and radicals in organic chemistry
  • Explore the concept of hyperconjugation in greater detail
  • Learn about the comparative basicity of different alkoxide ions
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Chemistry students, organic chemists, and anyone interested in understanding the factors influencing base strength in organic reactions.

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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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