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JEE Main levelSingle correct optionDifficulty 2 of 3nc153

Aniline does not undergo Friedel-Crafts alkylation or acylation because

  1. Athe basic amino group forms a salt-like complex with , which strongly deactivates the ring
  2. Bthe ring of aniline is deactivated by the -I effect of the amino group
  3. Caniline is oxidised by
  4. Dthe amino group is meta-directing and blocks the ortho and para positions

Answer: A

The nitrogen lone pair coordinates to the Lewis acid AlCl3 to form a positively charged adduct. This nitrogen is strongly electron withdrawing, so the ring is deactivated and the reaction does not proceed.
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