EXAM42007KEY

EXAM42007KEY - CHEMISTRY 2261 EXAM 4 November 28, 2006 LIST...

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CHEMISTRY 2261 November 28, 2006 EXAM 4 NAME (PRINT)____________________________________________ 1 2 3 4 5 6 7 8 9 10 11 TOTAL LIST number Answer Key 1. (6 pts, 3 pts ea) Give the major product(s) of each of the following reactions. 2. (20 pts, 4 pts ea) Indicate reagents and conditions for the following transformations. N 3 OMe O NC NC CN 1. 2. MeMgBr (then H 2 O) 3. PBr 3 , pyridine 4. NaCN R O O OH 1. 2. MeMgBr (then H 2 O) 3. TsCl, pyridine 4. NaCN R O O OH 1. NBS, h ! (or # ) 2. NaCN 2. MeONa (then H 2 O) (or 2. MeOH, H + ) R O O OH 1. 3. PCC (or H 2 CrO 4 ) 1. Br 2 2. NaNH 2 (2 eq) 3. 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 Br NaCN OH PBr 3 , pyridine O BrMg react, then H + quench R O OH O Br Mg NBS h ! or # 4. (8 pts, 4 pts ea) Suggest an efficient reaction sequence for each of the indicated transformations: a) 1. NBS 2. MeMgBr 1. R O O OH also possible: 2. MeMgBr 3. TsCl, pyridine 4. tBuO b) OH 1. Br 2 , h ! or # 2. BH 3 3. HOOH, NaOH
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3 5. (20 pts, 4 pts ea)
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This note was uploaded on 06/09/2011 for the course CHEM 2261 taught by Professor Crowe during the Spring '08 term at LSU.

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EXAM42007KEY - CHEMISTRY 2261 EXAM 4 November 28, 2006 LIST...

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