JEE Advanced levelSingle correct optionDifficulty 3 of 3g2209
The pKa values in water are 3.25 for 2,6-dimethylbenzoic acid and 4.37 for 4-methylbenzoic acid. The value of Ka(2,6-dimethyl)/Ka(4-methyl) is closest to
A1.3
B0.076
C130
D13
Answer: D
Ka=10−pKa, so the ratio =104.37−3.25=101.12=13.2. The two ortho methyl groups twist COOH out of the ring plane (steric inhibition of resonance), which makes the acid much stronger even though methyl is a donor.