Phenol (hydroxybenzene) behaves as a weak acid. a) Write out the equilibrium equation for its partial dissociation in water. b) Write out the expression for the acid dissociation constant, K₂. d) Draw the conjugate base of phenol and show how it is stabilised by resonance. e) Compare and explain the acidity of phenol (PK = 9.9) with that of: cyclohexanol (PK₁ = 16.0) 3-fluorophenol (p=9.3) 4-acetylphenol (p = 8.1)

Chemistry: Principles and Reactions
8th Edition
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:William L. Masterton, Cecile N. Hurley
Chapter22: Organic Chemistry
Section: Chapter Questions
Problem 60QAP: Write an equation for the reaction of chloroacetic acid (Ka=1.5103) with trimethylamine (Kb=5.9105)...
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Phenol (hydroxybenzene) behaves as a weak acid.
a) Write out the equilibrium equation for its partial dissociation in water.
b) Write out the expression for the acid dissociation constant, Ka.
d) Draw the conjugate base of phenol and show how it is stabilised by resonance.
e) Compare and explain the acidity of phenol (p = 9.9) with that of:
cyclohexanol (pk = 16.0)
3-fluorophenol (pK₁ = 9.3)
4-acetylphenol (pK, = 8.1)
Transcribed Image Text:Phenol (hydroxybenzene) behaves as a weak acid. a) Write out the equilibrium equation for its partial dissociation in water. b) Write out the expression for the acid dissociation constant, Ka. d) Draw the conjugate base of phenol and show how it is stabilised by resonance. e) Compare and explain the acidity of phenol (p = 9.9) with that of: cyclohexanol (pk = 16.0) 3-fluorophenol (pK₁ = 9.3) 4-acetylphenol (pK, = 8.1)
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