Why ortho carboxylic acid is more acidic than para carboxylic acid?
Explanation of why ortho carboxylic acid is more acidic than para carboxylic acid:
Introduction:
Carboxylic acids are acidic compounds due to the presence of a carboxyl group (-COOH). The strength of the acid is determined by the stability of the conjugate base. The acidity of carboxylic acids is influenced by the position of the carboxyl group in relation to the other substituents on the aromatic ring.
Resonance stabilization:
The carboxyl group can undergo resonance stabilization with the aromatic ring. This resonance effect stabilizes the conjugate base by delocalizing the negative charge over a larger area. The more stable the conjugate base, the more acidic the carboxylic acid.
Effect of position of carboxyl group:
The position of the carboxyl group in relation to the other substituents on the aromatic ring determines the extent of resonance stabilization. Ortho and para positions are more favorable for resonance stabilization than the meta position.
Ortho vs para carboxylic acid:
In ortho carboxylic acid, the carboxyl group is located in the ortho position (1,2) relative to the other substituents on the aromatic ring. In para carboxylic acid, the carboxyl group is located in the para position (1,4) relative to the other substituents on the aromatic ring.
Effects of ortho position:
The ortho position is more favorable for resonance stabilization because it allows for maximum overlap between the p-orbitals of the carboxyl group and the aromatic ring. This results in a more stable conjugate base and a stronger acid.
Effects of para position:
The para position is less favorable for resonance stabilization because it allows for less overlap between the p-orbitals of the carboxyl group and the aromatic ring. This results in a less stable conjugate base and a weaker acid.
Conclusion:
In summary, ortho carboxylic acid is more acidic than para carboxylic acid because the ortho position allows for maximum resonance stabilization of the conjugate base. The para position, on the other hand, allows for less resonance stabilization, resulting in a weaker acid.
Why ortho carboxylic acid is more acidic than para carboxylic acid?
Ortho effect occurs when a group present in the ortho position with respect to carboxylic group creates steric strain resulting in rotation of the carboxylic group and shifting it out of plane of the benzene ring….thus..the carboxylic group can no longer participate in ring resonance and thereby the acidity increases as delocalization of negative charge on the conjugate base of the acid is improved This is called ortho effect