In alkoxide ions, the negative charge is localized on oxygen, while in phenoxide ions, the charge is delocalized. The delocalization of charge in phenoxide ions contributes to their increased stability compared to the localized charge in alkoxide ions.
How does the localization of negative charge in alkoxide ions differ from the delocalization of charge in phenoxide ions, and what is the significance in their stabilities?
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In alkoxide ions, negative charge is localized on a single oxygen atom. In contrast, in phenoxide ions, negative charge is delocalized over the entire aromatic ring through resonance. The significance lies in the stability of the ions. Phenoxide ions are more stable due to the resonance stabilization, spreading the negative charge across multiple atoms. This makes phenoxide ions less reactive and more resistant to attack by electrophiles. In alkoxide ions, the localized charge makes them more reactive. The delocalization in phenoxide ions contributes to the enhanced stability and unique reactivity patterns observed in phenolic compounds.