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JEE Main levelSingle correct optionDifficulty 2 of 3g2143

Given : benzoic acid 4.20, 4-nitrobenzoic acid 3.44, 3-nitrobenzoic acid 3.45, 2-nitrobenzoic acid 2.17. Which is the strongest acid, and why is it stronger than the para isomer?

  1. A4-Nitrobenzoic acid; the nitro group exerts both and effects there
  2. B3-Nitrobenzoic acid; only a effect operates
  3. C2-Nitrobenzoic acid; the ortho group adds the steric ortho effect to its electron-withdrawing effect
  4. DBenzoic acid; it has no electron-withdrawing group

Answer: C

The ortho isomer has 2.17, the lowest. An ortho group twists the out of the ring plane (steric inhibition of resonance), which adds to the strong effect of at close range. The para and meta isomers (3.44, 3.45) lack the steric component.
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