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Which is the weakest base in aqueous solution among aniline, 4-methylaniline, 3-methylaniline and 2-nitroaniline?

  1. AAniline
  2. B4-Methylaniline
  3. C2-Nitroaniline
  4. D3-Methylaniline

Answer: C

The nitro group is strongly electron-withdrawing and, in the ortho position, also hinders solvation and protonation of the amino group. The conjugate acid of 2-nitroaniline has against 4.6 for anilinium, so it is far weaker than aniline. The methyl-substituted anilines are not weaker than aniline in this series.
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