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The PHENOXIDE ion is more STABLE than the ethoxide ion because
Athe ethoxide ion is destabilised by hydrogen bonding
Bthe phenoxide ion is smaller in volume
Cthey are equally stable; there is no difference
Dphenoxide resonance delocalises the negative charge
Answer & Solution
Correct answer: D. phenoxide resonance delocalises the negative charge
1. Phenol's conjugate base, the phenoxide $\mathrm{C_6H_5O^-}$, has 4 important resonance structures: one with the negative charge on O, and three with the charge on the ortho/para ring carbons.
2. RESONANCE DELOCALISATION lowers the energy of the phenoxide ion, making it more STABLE.
3. Ethoxide $\mathrm{CH_3CH_2O^-}$ has NO such resonance — the negative charge is LOCALISED entirely on the single O atom.
4. More stable conjugate base means STRONGER parent acid: this is why phenol ($\mathrm{pK_a}\sim 10$) is much more acidic than ethanol ($\mathrm{pK_a}\sim 16$).
5. The electron-DONATING alkyl group in ethoxide ($\mathrm{+I}$ effect) further destabilises the negative charge — a separate factor reinforcing the same conclusion.
6. Options B–D have no chemical basis.
_Source: NCERT Class 12 Chemistry Part 2, Ch 7, §7.4 (Acidity of phenol — resonance argument), p. 15._
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