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EXAM22008 - OH OH Cl OH O OH Br Br 5(12 pts 3 pts ea...

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CHEMISTRY 2261 October 8, 2008 EXAM 2 NAME (PRINT)____________________________________________ 1 2 3 4 5 6 7 8 TOTAL LIST number 1. (15 pts) Indicate (circle) high priority groups and assign ( Z ) or ( E ) configuration to the following compounds. You will not get credit for your ( Z ) or ( E ) choice unless you assign correct priorities. HS O example (a) (b) Cl F ( E ) F NH 2 Cl CO 2 H NC H 2 N F F N H O (c) (d) (e) O H Br Cl 2. (8 pts) Draw structures corresponding to the following IUPAC names. 3-isobutyl-5,6-dimethyl-3-cyclohexenol 4- sec -butyl-3-ethyl-2-cyclobutenol
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2 3. (25 pts, 5 pts ea) Provide the alkene and reaction conditions for each of the following transformations. a) b) d) c) e) Cl OH Cl OH OMe Br OH
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3 4. (12 pts, 2 pts ea) Indicate reagents and conditions for the following transformations.
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Unformatted text preview: OH OH Cl OH O OH Br Br 5. (12 pts, 3 pts ea) Provide a single alkene which can be converted to all of the indicated products and give reagents and conditions for each transformation. (a) (b) (c) (d) OH OH OH 4 6. (15 pts, 3 pts ea) Give the major product of each of the following addition reactions. a) b) d) c) HBr HBr Cl 2 H 2 O peroxide R O O OH e) H 2 O H + 5 7. (10 pts) Provide a mechanism for the following reaction. HO H 3 O + O 8. (3 pts) Draw the most stable isomer of the alkene heptene (C 7 H 14 ). most stable isomer of heptene (C 7 H 14 )...
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