PS7_soln - particular sequence in these problems Br COOH NO 2 Cl NO 2 O O OH Br Start with toluene(provides para directing abilty 1 HNO 3 H 2 SO

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Name ____________________________ 1 P r o b l e m S e t 7 D u e D e c e m b e r 1 st Problems worth understanding Ch 14. 25, 27, 33, 40, 44, 57 Ch 15. 30, 34, 37, 41, 44 (NMR problems for practice) Ch 16. 30, 31, 35, 36, 42, 44, 49, 50, 59, 65, 70 1. Provide the major products for the following reactions. OCH 2 CH 3 OMe O OMe O OH Br O MeO O MeO Br SO 3 H SO 3 H OCH 2 CH 3 Cl OCH 2 CH 3 Cl Br Br Br OH Br OH Br SO 3 H 2 SO 4 Cl 2 , FeCl 3 CH 3 Cl, AlCl 3 + NBS, CCl 4 + CH 3 Cl, AlCl 3 EDG EWG Diels Alder Diels Alder EDG EWG Major Steric Hindrance Major Major + + + + Major
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Name ____________________________ 2 2. Please circle the compounds that are aromatic based upon Hückels rules. Also indicate how they fulfill Hückels rules. Cyclic, conjugated, planar and 4n + 2 electrons in p orbitals. Individual p orbitals can be filled or empty as long as the total electron count of the π system is 4n + 2. S - - - + + N - N H .. .. .. .. .. ..
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Name ____________________________ 3 3. Provide a reasonable synthesis for the following compounds, starting from either benzene or toluene, utilizing all reaction you know to date. It is important that you realize that the electrophilic aromatic substitutions have to be done in a
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Unformatted text preview: particular sequence in these problems. Br COOH NO 2 Cl NO 2 O O OH Br Start with toluene (provides para directing abilty) 1. HNO 3, H 2 SO 4 (meta directing abilty ) 2. Br 2, FeBr 3 3. KMnO 4 Start with benzene 1. CH 3 CH 2 COCl, AlCl 3 provides meta-directing abilty 2. Cl 2 , FeCl 3 3. H 2 , Pd/C reduction results in alkyl group that provides ortho-directing ability 4. HNO 3 , H 2 SO 4 Make each of these compounds seperately and add them together in the presence of a hindered base Start with Benzene 1. CH 3 CH 2 COCl, AlCl 3 2. H 2 , Pd/C 3. NBS, CCl 4 4. Na + -OCH(CH 3 ) 2 Name ____________________________ 4 4. Give a complete arrow pushing mechanism fro the following reactions. OH OH O OH Br H 3 O + HBr Hint: 5 steps and the last step involoves keto-enol tautomerization Hint: 4 steps and the third step involves a hydride shift...
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This note was uploaded on 05/03/2009 for the course CHEM 242A taught by Professor Staff during the Spring '06 term at University of Arizona- Tucson.

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PS7_soln - particular sequence in these problems Br COOH NO 2 Cl NO 2 O O OH Br Start with toluene(provides para directing abilty 1 HNO 3 H 2 SO

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