Charge delocalization, illustrated by resonance structures I-V, increases the stability of phenoxide ions. The phenol molecule is less stable due to charge separation in its resonance structures, favoring the ionization of phenol.
What role does charge delocalization play in the stability of phenoxide ions, and why is the phenol molecule less stable than the phenoxide ion?
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Charge delocalization in phenoxide ions increases their stability. In phenoxide ions, the negative charge is delocalized over the aromatic ring through resonance, creating a more stable structure. The negative charge is spread across multiple atoms, reducing the energy of the ion and making it less reactive. In contrast, the phenol molecule is less stable than the phenoxide ion because it lacks this charge delocalization. The lone pair on the oxygen is localized, making the oxygen more nucleophilic and the molecule more reactive. Phenol readily donates a proton, forming the more stable phenoxide ion.