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FINAL EXAM KEY

FINAL EXAM KEY - CHEMISTRY 2261 FINAL EXAM NAME(PRINT 1 2 3...

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CHEMISTRY 2261 December 14, 2007 FINAL EXAM NAME (PRINT)____________________________________________ 1 2 3 4 5 6 7 8 TOTAL 9 LIST number Answer Key 1. (8 pts, 4 pts ea) Provide the required diene and dienophile for each of the following Diels-Alder reactions. a) b) MeO 2 C OMe OMe MeO 2 C O OMe MeO OMe OMe CO 2 Me CO 2 Me O OMe MeO 2. (15 pts, 3 pts ea) Indicate reagents and conditions for the following transformations. CN OH OMe CN OMe OH CO 2 H 1. NBS, h Q 2. NaCN 1. HBr, peroxide 2. NaCN 1. 2. MeO , MeOH 1. 2. MeOH, H + R O O OH R O O OH 1. BH 3 2. HOOH, NaOH 3. H 2 CrO 4
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2 3. (10 pts) Suggest an efficient reaction sequence for the preparation of the following compound from the indicated starting materials and any other necessary reagents. from and Br O HO HO O NaOH HO R O OH O MgBr O R O OH O Mg then H + 4. (8 pts) Provide a mechanism for the following reaction. HO H 2 SO 4 ' H + OH 2 + + + H B
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3 5. (10 pts, 2 pts ea) Assuming planar structures, characterize the following compounds as aromatic, antiaromatic, or nonaromatic.
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