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Method / Topic: Organic Chemistry
Deprotonation of phenol gives phenoxide, whose negative charge can be delocalized into the aromatic ring through resonance. The cyclohexoxide charge remains largely localized on oxygen. Greater conjugate-base stability makes the parent acid stronger, so phenol has the lower pKa. This conclusion follows from electron flow, functional-group behavior, and the stated experimental conditions. For MCAT organic chemistry, first mark the nucleophile, electrophile, leaving group, and any resonance-stabilized intermediate; then track bonds rather than memorizing a product name. Check stereochemistry, charge, and carbon count before choosing an
, and interpret evidence without overclaiming. Always reconcile the proposed structure with every observation in the
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Correct Answer:
Method / Topic: Organic Chemistry
Deprotonation of phenol gives phenoxide, whose negative charge can be delocalized into the aromatic ring through resonance. The cyclohexoxide charge remains largely localized on oxygen. Greater conjugate-base stability makes the parent acid stronger, so phenol has the lower pKa. This conclusion follows from electron flow, functional-group behavior, and the stated experimental conditions. For MCAT organic chemistry, first mark the nucleophile, electrophile, leaving group, and any resonance-stabilized intermediate; then track bonds rather than memorizing a product name. Check stereochemistry, charge, and carbon count before choosing an
, and interpret evidence without overclaiming. Always reconcile the proposed structure with every observation in the
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