Organic ChemistryMain MenuLecture 1: Introduction to Molecular OrbitalsLecture 10: Intermolecular Forces and Intro to ReactivityLecture 11: Alkenes as Nucleophiles ILectures 12 and 13: Alkenes II & IIILecture 14: Benzenes as Nucleophiles ILecture 15 objectives and skillsLecture 2: Molecular Orbitals in Organic StructuresLecture 3: Molecular Orbitals and ResonanceLecture 4: Molecular Orbitals and AromaticityLecture 5: Nomenclature and IR SpectroscopyLecture 6: Stereochemistry ILecture 7: Stereochemistry IILecture 8: Newman and Fisher ProjectionsLecture 9: Conformations and Cyclohexane RingsJulio Terra2fb22914f73f9e5a767bf7fb83987dca0e153e4a
12020-03-01T15:12:21-08:00SOLUTION 10.3c1plain2020-03-01T15:12:21-08:00Carboxylic acids and phenols both have resonance stabilization of their conjugate bases, which makes them stronger acids than aliphatic alcohols. Carboxylate salts have equal distribution of anionic charge across both oxygens. This makes the anion more stabilized (weaker base), thus the acid is the stronger acid as compared to phenol. In phenols, there are more resonance structures, but they are not all equal. The contributor with aromatic ring and localized oxygen anion is the best contributor, so charge is less equally delocalized than in a carboxylic acid. Between the two carboxylic acids, the one with the fluorine has the strongest inductive EWG effects, which helps stabilize the anionic conjugate base (or polarize the acidic OH).
