1. Illustrate using resonance structures how a moderate, to strong, electron-withdrawing group (e.g. -NO2, −COR, etc.) decreases the nucleophilicty of particular sites on an aromatic ring (before the addition of an electrophile).    

2. Explain why bromination is favoured at the 2′-postion, as opposed to the 3′-position, of the aromatic ring.    

3. Provide a full mechanism for the synthesis of 2′-bromo-4’methylacetanilide starting from HOBr and 4′-methylacetanilide. Show all nonzero formal charges, intermediates and important resonance structures.  use arrows to clearly show bonds forming or breaking between atoms