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Electron-withdrawing groups enhance carboxylic acid acidity, stabilizing the conjugate base, while electron-donating groups decrease acidity. The increasing acidity order of substituents is Ph < I < Br < Cl < F < CN < NO₂ < CF₃.

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Substituents affect carboxylic acid acidity by influencing the stability of the conjugate base. Electron-withdrawing groups increase acidity by stabilizing the conjugate base through inductive and/or resonance effects, while electron-donating groups decrease acidity by destabilizing the conjugate base.

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Carboxylic acids are more acidic than phenols because the carboxylate ion, the conjugate base of carboxylic acids, is more stabilized with two equivalent resonance structures, while the phenoxide ion has non-equivalent resonance structures, leading to less effective delocalization and lower ...

Prataps

Carboxylic acids are among the most acidic organic compounds due to the stabilization of their conjugate base, the carboxylate ion, through two equivalent resonance structures. This contrasts with phenols, where the phenoxide ion has non-equivalent resonance structures, making carboxylic acids ...