Why does cyclohexanol have a pK, of 18 and phenol, despite its similarities in structure, have a pK, of 10? Phenol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Cycohexanol has a resonance-stabilized structure, which increases its stability and reduces the likelihood that it will react to form a conjugate base Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and inhibits its formation Cycohexanol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and favors its formation

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter19: Enolate Anions And Enamines
Section: Chapter Questions
Problem 19.63P
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Why does cyclohexanol have a pK, of 18 and phenol, despite its similarities
in structure, have a pK, of 10?
Phenol has a resonance-stabilized conjugate base, which increases the stability of
the base and favors its formation
Cycohexanol has a resonance-stabilized structure, which increases its stability and
reduces the likelihood that it will react to form a conjugate base
Phenol has a resonance-stabilized conjugate base, which decreases the stability of
the base and inhibits its formation
Cycohexanol has a resonance-stabilized conjugate base, which increases the
stability of the base and favors its formation
Phenol has a resonance-stabilized conjugate base, which decreases the stability of
the base and favors its formation
Transcribed Image Text:Why does cyclohexanol have a pK, of 18 and phenol, despite its similarities in structure, have a pK, of 10? Phenol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Cycohexanol has a resonance-stabilized structure, which increases its stability and reduces the likelihood that it will react to form a conjugate base Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and inhibits its formation Cycohexanol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and favors its formation
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