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JEE MainChemistryHydrocarbons

Which of the following sets of aromatic compounds completely fails to undergo Friedel-Crafts alkylation?

Options

  1. AChlorobenzene, acetophenone, benzaldehyde
  2. BToluene, nitrobenzene, benzoic acid
  3. CAnisole, aniline, cyanobenzene
  4. DAniline, nitrobenzene, benzoic acid

Correct answer

D. Aniline, nitrobenzene, benzoic acid

Step-by-step solution

Friedel-Crafts alkylation and acylation reactions do not occur on strongly deactivated benzene rings. Groups like - NO₂ , - COOH , - CHO , - CN , and - COR are strong electron-withdrawing groups that decrease the electron density on the benzene ring to such an extent that the electrophile cannot attack it. Furthermore, aniline has an - NH₂ group which acts as a Lewis base. It reacts with the Lewis acid catalyst (like AlCl₃ ) to form a strongly deactivated complex, thus preventing the Friedel-Crafts reaction. Chloro

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