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Question: Answered & Verified by Expert
The ionization constant of phenol is higher than that of ethanol because :
ChemistryGeneral Organic ChemistryBITSATBITSAT 2014
Options:
  • A Phenoxide ion is bulkier than ethoxide
  • B Phenoxide ion is stronger base than ethoxide
  • C Phenoxide ion is stabilized through delocalization
  • D Phenoxide ion is less stable than ethoxide
Solution:
2120 Upvotes Verified Answer
The correct answer is: Phenoxide ion is stabilized through delocalization
The acidic nature of phenol is due to the formation of stable phenoxide ion in solution

$$

\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{OH}+\mathrm{H}_{2} \mathrm{O} \rightleftharpoons \mathrm{C}_{6} \mathrm{H}_{5} \mathrm{O}_{\text {Phenoxide ion }}^{-}+\mathrm{H}_{3} \mathrm{O}^{+}

$$

The phenoxide ion is stable due to

resonance.




The negative charge is delocalized in the benzene ring which is a stabilizing factor in the phenoxide ion and increase acidity of phenol. wheras no resonance is possible in alkoxide ions $\left(\mathrm{RO}^{-}\right)$ derived from alcohol. The negative charge is localized on oxygen atom. Thus, alcohols are not acidic.

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