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3,5 - dimethyl 4-amino Benzoic acid OR 2,6 - dimethyl 4-amino Benzoic acid .. Which one is more acidic and also the reason .. Please help me out

3,5 - dimethyl 4-amino Benzoic acid OR 2,6 - dimethyl 4-amino Benzoic acid ..

Which one is more acidic and also the reason ..


Please help me out 

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5 Answers

Swapnil Saxena
102 Points
10 years ago

3,5 dimethyl 4ammino benzoic acid is more acidic as Positive inductive groups r present far away to the COOH gourp resulting in more acidities than 3,6 dimethyl benzoic acid.

Neelay Bharani
4 Points
10 years ago

What about Steric hindrance of resonance taking place due to bulky groups and all ?

G Narayana Raju
51 Points
10 years ago

2,6 - dimethyl 4-amino Benzoic acid  is more acidic .       

due to ortho effect it is more acidic.

ortho effect means:if any group present on ortho position of benzoic acid it always increases acidic nature of acid because this group decreases outer resonance of ring towards acid which increases acidic nature for example orthonitrobenzoic acid is most acidic in any nitro derivative of benzoic acid.orthomethyl benzoic acid is maximum acidic than other isomers.similarly if any group present on ortho position of aniline it decreases basic nature.

Swapnil Saxena
102 Points
10 years ago

Sorry,  just missed the Ortho effect (Steric Inhibition of Resonace). The ortho substitutued for is more acidic irrecpective of the inductive effect it produces. 2,6 dimethyl 4-ammino benzoic acid is more acidic.

Neelay Bharani
4 Points
10 years ago

Thank you , are you certain of the answer ?

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