Note: Radical bromination of an alkane, one of the only reactions an alkane will undergo. Note regioselectivity based on relative stability of the radical intermediate at the more highly substituted carbon

Note: Benzylic radicals are unusually stable, resulting in the regioselective preference over the tertiary position

Warning: Allylic radicals are unusually stable like benzylic radicals, but Br₂ is more likely to simply add to the alkene π bond