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Phenols do not exhibit the same pKa values as other alcohols; they are generally more acidic. Using the knowledge that hydrogen acidity is directly related to stability of the anion formed (the conjugate base), explain why phenol is much more acidic than cyclohexanol.
Draw three second-order resonance structures for phenol.
a. Explain why the second-order resonance contributors are less important than first-order resonance structures, and contribute only a small amount to our overall understanding of phenol.
b. Explain the following statement:The second-order resonance structures help explain why substituents with a lone pair (such as a -OH) activate the ortho and para positions toward electrophilic aromatic substitution (EAS).