Question

Draw out the detailed mechanisms for each step of bromination of acetanilide, aniline, and anisole while including the most stable resonance contributor for each intermediate. Then rank the three in order of activating ability and clearly explain why.

C-CH3 NH2 OCH3 Acetanilide Aniline Anisole

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Br2 FeBr3 оснз + FeBr4 Br-Br-FeBij+ FeBi4 oCH3 HBrFeBr3Ortho attack Para attack NH Br NH Br- Br Br Br-Br (plus other resonance forms) H Br (plus other resonance forms)0% 0% O: H-N-C H-N-C CH2 CH Br-Br:- + HBr H Br Brare orhc para direchng rarp trwareb Ai these roups electreoplilk siubsthrtution of ben zene ing cpS auta orcho N is less elec

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