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Problem_Set_3_solutions

Problem_Set_3_solutions - Chem 3580 Spring 2009 Problem...

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Chem 3580 - Spring 2009 Problem Set #3 - Solutions 1. 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 NO 2 NO 2 Cl NO 2 NO 2 Br NO 2 Br NO 2 NH 2 NO 2 Cl m- m- Both NO 2 groups direct meta. All positions that can be brominated are identical NO 2 directs meta and Br directs ortho and para, but the para position is blocked. m- o- NH 2 , a strong activator, directs ortho and para but para is blocked. NO 2 directs meta. o- m- 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 CH 3 COOH Cl NO 2 Cl O 2 N NO 2 Cl Br NO 2 Cl Br + OCH 3 Br NO 2 OCH 3 Br O 2 N + NO 2 Cl NO 2 + OCH 3 is a strong activator, directs ortho and para; Br also directs ortho and para. Mixture of products OCH 3 activator; controls regiochemistry. Para position is blocked. Positions that can be chlorinated are identical No 2 strong deactivator; directs meta. Cl directs ortho and para. Para product is the major one for steric considerations.
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