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What is The reason that any group joined at Ortho position always increases the acidity in case of carboxylic acid and amines ??

What is The reason that any group joined at Ortho position always increases the acidity in case of carboxylic acid and amines ??

Grade:12

2 Answers

Harshit Gupta
22 Points
6 years ago
The group at ortho position causes steric inhibition of resonance (SIR effect) which makes the lone pair of functional group localized and hence they are available for donation. Therefore basicity increases. 
Harshit Gupta
22 Points
6 years ago
The group at ortho position (whether it is +I or - I) always increases acidic strength in carboxylic acids because the conjugate base formed (after removing H+) and the group at ortho position get repelled which makes the conjugate base group out of the plane of benzene ring inhibiting the resonace between benzene ring and base group. Now the electrons of the group can only resonate within itself forming the two equivalent resonating structures. We know rhat the molecule  forming equivalent resonating structures are most stable. 
Therefore this carboxylic acid is most acidic due to formation of most stable conjugate base

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