Answer to Question #157969 in Organic Chemistry for sally

Question

Use the concept of charge delocalization by extended π bonding (resonance) to explain why

RCOOH (pKa5) is more acidic than ROH (pKa15).

Answer 1

Delocalization of electrons decreases charge density, increasing stability. An acid with a conjugate base that has delocalized electrons due to resonance is more acidic than an acid with a conjugate base with localized electrons.