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FINAL2009KEY - CHEMISTRY 2261 FINAL EXAM December 9 2009...

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CHEMISTRY 2261 December 9, 2009 FINAL EXAM NAME (PRINT)____________________________________________ 1 2 3 4 5 6 7 TOTAL LIST number 1. (6 pts, 3 pts ea) Give the major product(s) of each of the following reactions. a) HBr + b) HI + O O OH O Br + + I Me 2. (12 pts, 3 pts ea) Indicate reagents and conditions for the following transformations (more than one step may be necessary). CN OH Br OMe Br OH OH 1. NBS, h ! 2. MeO 1. 2. NaCN then H + R O O OH Br 2 , H 2 O 1. 2. HBr R O O OH
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2 3. (12 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 OH BrMg O Br Br 2 , FeBr 3 Mg combine, then H + quench R O O OH AlCl 3 Br NBS, h ! Br MgBr is another possibility 4. (8 pts) Provide a mechanism for the following reaction. OH 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. aromatic antiaromatic nonaromatic aromatic antiaromatic nonaromatic aromatic antiaromatic nonaromatic aromatic
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