Reactions
Reactants Reagents Products Help
CC(=C)C Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
CC(=C)CBr Magnify

Note: NBS under radical conditions provides a milder alternative for performing allylic radical bromination


Cc1ccccc1 Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
c1ccc(cc1)CBr Magnify

Note: NBS works for benzylic bromination similar to Br2


CC1CCCCC1 Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
Magnify

Note: NBS is not strong enough to brominate completely non-activated alkanes (no allylic or benzylic positions)


CC[C@H](C)c1ccccc1 Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
CC[C@](C)(c1ccccc1)Br Magnify

Note: Radical bromination proceeds through an achiral (planar) radical intermediate, resulting in the racemization of affected chiral centers
CC[C@@](C)(c1ccccc1)Br Magnify


CCC=C Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
C/C=C/CBr Magnify

Note: Allylic radicals have multiple resonance forms, resulting in multiple possible sites for addition and thus a mixture of multiple possible products
C[C@H](C=C)Br Magnify C[C@@H](C=C)Br Magnify


Cc1ccccc1 Magnify N1(Br)C(=O)CCC1=O
Light, Peroxide
c1ccc(cc1)CBr Magnify

Note: Benzylic carbons can be brominated with NBS and peroxide, or Br2 and light


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