Asked in PMC Practice Test 14 (2021) 2021Moderate

Why is phenol more acidic than alcohol?

Correct answer: C. Both Options A and B are correct

  • A. Due to presence of resonance in phenol
  • B. Due to the absence of resonance in alcohol
  • C. Both Options A and B are correct
  • D. Because in phenol, hydrogen is attached to oxygen

Explanation

The answer is Both Options A and B are correct. Phenol is more acidic than alcohol because of two reasons: The presence of resonance in phenol. The oxygen atom in phenol is bonded to a hydroxyl group (-OH). The electron pair on the oxygen atom is shared with the hydrogen atom, but it can also be delocalized over the benzene ring. This delocalization of electrons makes the phenol molecule more stable, and it also makes the hydrogen atom more acidic. The absence of resonance in alcohol. The oxygen atom in alcohol is bonded to a hydroxyl group, but the electron pair on the oxygen atom is not delocalized. This makes the alcohol molecule less stable, and it also makes the hydrogen atom less acidic.

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About Phenols

Phenols contain a hydroxyl group directly bonded to an aromatic ring, making them more acidic than alcohols because the phenoxide ion is resonance-stabilised. Reactions include ionisation with bases, electrophilic substitution, bromination, nitration and oxidation, with attention to the difference between phenols and aliphatic alcohols.

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