Although phenoxide ion has more no. of resonating structures than carb...
Because conjugate base of carboxylic acid has equivalent resonating structures that r more stable over normal resonating structures..
Although phenoxide ion has more no. of resonating structures than carb...
Introduction:
Phenol and carboxylic acids are both organic compounds that contain an acidic hydrogen atom. However, carboxylic acids are generally stronger acids than phenols. This can be explained by understanding the structural and electronic factors that influence the acidity of these compounds.
Electronic Factors:
1. Resonance stabilization: The carboxylate ion is stabilized by resonance, where the negative charge is delocalized over two oxygen atoms. This resonance stabilization makes the carboxylate ion more stable and therefore, more acidic.
On the other hand, the phenoxide ion also has resonance structures, but the negative charge is delocalized only over one oxygen atom. This makes the phenoxide ion less stable compared to the carboxylate ion, resulting in a weaker acid.
2. Inductive effect: The carboxylate ion experiences a greater inductive effect compared to the phenoxide ion. This is because the electronegative oxygen atoms in the carboxylate ion pull electron density away from the carboxylate group, making it more acidic.
In contrast, the phenoxide ion experiences a smaller inductive effect as the oxygen atom is less electronegative than in the carboxylate ion. Therefore, the phenoxide ion is less acidic than the carboxylate ion.
Structural Factors:
1. Hydrogen bonding: Carboxylic acids can form intermolecular hydrogen bonds due to the presence of both the hydrogen atom and the carbonyl group. This enhances the stability of carboxylic acids and makes them more acidic.
Phenols, on the other hand, can only form intramolecular hydrogen bonds due to the presence of a single oxygen atom. This results in weaker hydrogen bonding and hence, weaker acidity compared to carboxylic acids.
Conclusion:
In conclusion, carboxylic acids are stronger acids than phenols due to the combined effects of resonance stabilization, inductive effect, and hydrogen bonding. The resonance stabilization and inductive effect in the carboxylate ion make it more stable and more acidic. Additionally, the ability of carboxylic acids to form intermolecular hydrogen bonds further enhances their acidity. Understanding these factors helps explain why carboxylic acids exhibit stronger acidic properties compared to phenols.