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Grade 11Organic Chemistry

Why is 2-methylbenzoic acid more acidic than benzoic acid?

Profile image of Janani Ramesh
15 Years agoGrade 11
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2 Answers

Profile image of Sanjeev Malik IIT BHU
15 Years ago

COOH is a bigger group. when there is CH3(it is also bigger than H) at ortho position it causes STERIC HINDRANCE for the resonance between COOH AND benzene. thus although COOH IS META DIRECTING or electron withdrawing but due to hindered reso it takes less electrons towards itself and thus easy for releasing H+. this also overtake the +I effect of ch3 .

Profile image of Sanjeev Malik IIT BHU
15 Years ago

IT IS A VALID RIGHT REASON. this hindrance factor is applied in many cases. it is being given by a teacher itself giving coaching for iit. you can check it in books too.

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