FINAL2007 - antiaromatic nonaromatic aromatic antiaromatic...

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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 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 2. (15 pts, 3 pts ea) Indicate reagents and conditions for the following transformations. CN OH OMe CN OMe OH CO 2 H
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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 4. (8 pts) Provide a mechanism for the following reaction. OH H 2 SO 4 !
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3 5. (10 pts, 2 pts ea) Assuming planar structures, characterize the following compounds as aromatic, antiaromatic, or nonaromatic. aromatic antiaromatic nonaromatic aromatic
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Unformatted text preview: antiaromatic nonaromatic aromatic antiaromatic nonaromatic aromatic antiaromatic nonaromatic aromatic antiaromatic nonaromatic choose one O O O N O 6. (8 pts) Which isomer of C 10 H 8 O shown below is the strongest acid? Provide an explanation in terms of resonance stabilization of the conjugate base. OH OH 7. (6 pts, 3 pts ea) Give the major product(s) of each of the following reactions. a) HBr + b) HI + O O 4 8. ( 20 pts, 2pts ea) Indicate reagents and conditions for each of the following transformations (each is one step). O Br O 2 N H 2 N Br CO 2 H 5 9. ( 15 pts, 3 pts ea) Indicate reagents and conditions for each of the following transformations (more than one step may be necessary). a) c) b) d) e) CN MgBr OH CN...
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