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MDCAT Chemistry QUESTION #73
Question 1 (Select all that apply)

Which of the following best explains why phenol reacts with aqueous NaOH, but alcohols do not?

  • Phenol is weakly acidic due to resonance stabilization of phenoxide ion.✔️
  • Phenol form hydrogen bonding that facilitates ionization.
  • Alcohols contain a strong O-H bond that cannot be broken by weak bases.
  • Phenol has a lower boiling point than alcohol.
Correct Answer Explanation

Phenol is about a million times more acidic than alcohol because the resonance stabilization of the phenoxide ion lowers the energy of the product, favoring the reaction with NaOH.