Problem_Set_3 - OCH 3 O Br (b) 3. Complete the following...

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Chem 3580 - Spring 2009 Problem Set #3 1. Taking into account resonance structures, rank the following in the order (most reactive one first) in which they will react in electrophilic aromatic bromination. Write down the major monobrominated product for each. N(CH 3 ) 3 CH 2 N(CH 3 ) 3 N(CH 3 ) 2 NHCOCH 3 2. Taking into account resonance structures, rank the compounds in each set in the order (least reactive first) in which they will react toward nitration. Write down the major mononitrated product for each. OCH 3 Cl OCH 3 Cl OCH 3 (a) O O
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Unformatted text preview: OCH 3 O Br (b) 3. Complete the following reactions by drawing the major product that would be formed. NO 2 NO 2 NO 2 NO 2 NO 2 Br NH 2 NO 2 Cl 2 AlCl 3 Br 2 FeBr 3 HNO 3 H 2 SO 4 Cl 2 AlCl 3 OCH 3 Br CH 3 COOH NO 2 NO 2 Br 2 FeBr 3 HNO 3 H 2 SO 4 Cl 2 AlCl 3 Cl Cl HNO 3 H 2 SO 4 4. Show how you would synthesize each of the following compounds starting from benzene. Make sure to show your retrosynthetic analysis. Cl Cl SO 3 H CH 3 Br NO 2 NO 2 HOOC COOH (a) (b) (c) NO 2 OCH 3 NO 2 (d)...
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