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MDCAT Chemistry QUESTION #4347
Question 1
Which of the following best explains why phenol reacts with aqueous $NaOH$, but alcohols do not?
  • Phenol has a lower boiling point than alcohol
  • Alcohols contain a strong O-H bond that cannot be broken by weak bases
  • Phenol forms hydrogen bonding that facilitates ionization
  • Phenol is weakly acidic due to resonance stabilization of phenoxide ion✔️
Correct Answer Explanation
Phenol ($C_6H_5OH$) is acidic ($pK_a \approx 10$) because the phenoxide ion ($C_6H_5O^-$) is stabilized by resonance with the benzene ring. Alcohols are not acidic enough to react with $NaOH$.