Is tert-butoxide a strong nucleophile?
Understand the Problem
The question is asking whether tert-butoxide can be classified as a strong nucleophile, which involves understanding its reactivity and the basic principles of nucleophilicity in organic chemistry.
Answer
A poor nucleophile
Tert-butoxide is a strong base but a poor nucleophile due to steric hindrance.
Answer for screen readers
Tert-butoxide is a strong base but a poor nucleophile due to steric hindrance.
More Information
Tert-butoxide is often used in elimination reactions (like E2) because its bulkiness makes it effective at deprotonation without serving as a strong nucleophile.
Tips
A common mistake is assuming that strong bases are also strong nucleophiles. Tert-butoxide is hindered by its bulky structure.
Sources
- Illustrated Glossary of Organic Chemistry - Tert-butoxide - chem.ucla.edu
- Reagent Friday: Potassium tert-butoxide - masterorganicchemistry.com
- Why is tert-butoxide often used in elimination reactions? - chemistry.stackexchange.com
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