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NEET levelSingle correct optionDifficulty 1 of 3nc022

Which statement about the basicity of toluidines and aniline is correct?

  1. A4-nitroaniline and aniline are equally basic
  2. B4-nitroaniline is more basic than aniline
  3. C4-methylaniline is more basic than aniline
  4. D4-methylaniline is less basic than aniline

Answer: C

A methyl group at the para position donates electrons (+I and hyperconjugation), making the lone pair of nitrogen more available, so 4-methylaniline is the stronger base. A nitro group withdraws electrons by -I and -R and lowers the basicity.
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