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JEE Main levelSingle correct optionDifficulty 2 of 3nc116

Among aniline, 2-methylaniline, 3-methylaniline and 4-methylaniline, the weakest base in water is

  1. Aaniline
  2. B3-methylaniline
  3. C4-methylaniline
  4. D2-methylaniline

Answer: D

The methyl group at the meta and para positions is electron releasing and increases basicity. An ortho substituent, whatever its electronic nature, lowers the basicity of aniline (ortho effect: steric hindrance to solvation and protonation of the anilinium ion). So 2-methylaniline is even weaker than aniline.
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