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Illustrate using resonance structures how a moderate, to strong, electron-withdrawing group (e. -NO 2 , COR, etc.
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
