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Diazonium Salts & ReactionsAmines

Which of these will not undergo azo coupling with benzene diazonium chloride: Aniline, Phenol, Anisole, or Nitrobenzene?

Expert Answer

Nitrobenzene. It has a strong electron-withdrawing group ( −NO2-NO_2 ) which deactivates the ring towards electrophilic substitution (attack by the diazonium cation)

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