challenge_solutions_problem_set_8

challenge_solutions_problem_set_8 - Cl Cl O Cl O O O Cl...

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Chem 359 Problem Set 8 Chapter 8: Organic Chemistry: A Biological Approach Key Ideas: 1. Huckel Rule 2. Electrophilic aromatic substitution 3. Aromatic directing groups Suggested Problems : 8.1-8.22, 8.29, 8.32, 8.33, 8.34, 8.37, 8.40, 8.42, 8.43, 8.44, 8.45, 8.49, 8.50, 8.51, 8.53, 8.54, 8.56, 8.57, 8.59, 8.60, 8.61, 8.62, 8.64 Challenge Problems: 1. Determine whether the following compounds are aromatic, anti-aromatic, or neither. N N N H N NH 2 N N H NH 2 O N N N H N N H NH N S N H H N N N H NH 2 O not planar 5 electrons N H H N H H H
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2. Synthesize the following compounds from benzene. NH 2 Br O HO NO 2 Br NO 2 Br NO 2 MeCl, AlCl 3 HNO 3 , H 2 SO 4 FeBr 3 , Br 2 O HO KMnO 4 H 2 , Pd OH OH O Br OH OH Br Cl O AlCl 3 OH OH Br O O OH O H 1. mCPBA 2. NaOH FeBr 3 , Br 2 O Cl AlCl 3 O Cl AlCl 3 1. mCPBA 2. NaOH
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Unformatted text preview: Cl Cl O Cl O O O Cl AlCl 3 Cl 2 , AlCl 3 MeCl, AlCl 3 H 2 , Pd Sorry I had to change this problem in order to show you a cool trick. Friedel-Crafts alkylation would not have worked because a carbocation rearrangement would have occurred during the alkylation process. HO 3 S O HO 3 S HO 3 S O O Cl Cl HO 3 S SO 3 , H 2 SO 4 MeCl, AlCl 3 AlCl 3 AlCl 3 HO 3 S Cl O O 2 N NH 2 HN O O 2 N O 2 N HNO 3 , H 2 SO 4 AlCl 3 Cl mCPBA NH 2 HN O AlCl 3 Cl Cl Cl NH 2 HN O HN O NO 2 HN O HNO 3 , H 2 SO 4 H 2 , Pd You dont know how to make amides So I guess you will have to buy that compound....
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This note was uploaded on 09/19/2008 for the course CHEM 3590 taught by Professor Ganem during the Fall '08 term at Cornell University (Engineering School).

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challenge_solutions_problem_set_8 - Cl Cl O Cl O O O Cl...

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