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EXAM42007 - CHEMISTRY 2261 EXAM 4 NAME(PRINT 1 2 3 4 5 6 7...

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CHEMISTRY 2261 November 28, 2007 EXAM 4 NAME (PRINT)____________________________________________ 1 2 3 4 5 6 7 8 9 10 11 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 2. (20 pts, 4 pts ea) Indicate reagents and conditions for the following transformations. N 3 OMe O NC NC CN
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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 CN 4. (8 pts, 4 pts ea) Suggest an efficient reaction sequence for each of the indicated transformations: a) b) OH
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3 5. (20 pts, 4 pts ea) Give the major product(s) (indicating stereochemistry where appropriate) of each of the following reactions. a) c) b) d) e) 1. Br 2 , h ! 2. 1. 2. HCl NaSPh 1. 2. BH 3 HOOH, NaOH Br 1. 2. Me 2 CuLi H + (quench) SnBu 3 Pd(PPh 3 ) 4 Et 3 N R O O OH O 3. POCl 3 , pyridine 0 °C 3. H 2 CrO 4
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4 6. (8 pts) Provide a mechanism for the following reaction. OH HO O H + 7. (12 pts, 3 pts ea) Predict the major alkene product formed from each of the following reactions.
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