Answers%20to%20PS7 - Cr O O O Me Ph HO Cr O O O Me Ph O Cr...

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Chem 242 Spring 2007 Answers to Problem Set 7 Question 1. Predict the major product of the following reactions. a) b) c) OH Ph 1. CrO 3 , pyridine 2. Ph 2 CuLi 3. EtMgBr 1. HOCH 2 CH 2 OH, H + 2. mCPBA 3. 1M HCl H Me Me Me O H Me O 1. Ph 3 PCH 2 2. maleic anhydride, heat H Me Me O OH Ph Me Et Ph O O O O CH 3 H H endo product
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Chem 242 Spring 2007 Question 2. Provide a complete mechanism for the reaction sequence in Question 1, part b (shown below). b) 1. HOCH 2 CH 2 OH, H + 2. mCPBA 3. dilute HCl H Me Me O H Me Me O O H Me Me O H + H Me Me O H HO OH H Me Me HO O OH H H Me Me H 2 O O OH H Me Me O OH H Me Me O O H H Me Me O O -H + (product from step 1) mCPBA (epoxidation) H Me Me O O O (product from step 2) H + H Me Me O O H H Me Me O OH H 2 O H Me Me H 2 O O OH H Me Me HO O OH H H Me Me O H H Me Me O O O O O O O -H +
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Chem 242 Spring 2007 Question 3. Provide a complete mechanism for the reaction sequence in Question 1, part c (shown below). c) OH Ph 1. CrO 3 , pyridine 2. Ph 2 CuLi 3. EtMgBr Me OH Ph Me Et Ph Me Ph OH
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Unformatted text preview: Cr O O O Me Ph HO Cr O O O Me Ph O Cr OH O O H N Me Ph O Ph Cu Ph Li Me Ph O Ph workup Me Ph O Ph (product of step 1) (product of step 2) Me Ph Ph Et MgBr O Et workup Me Ph Ph OH Et Chem 242 Spring 2007 Question 4. Provide reagents that will accomplish the following transformations as efficiently as possible. Multiple steps may be needed. a) b) c) Me Me Me O O Me Me Me Me Me OH HO O HN Me Me Me Me Br Me Me Me Me O Me Me c) 1. O 3 2. SMe 2 (reductive workup) 3. NaBH 4 or LiAlH 4 aniline, NaBH 4 1. BH 3 2. H 2 O 2 , NaOH 3. K 2 Cr 2 O 7 , H 2 SO 4 4. CF 3 CO 3 H 1. Mg 2. isobutyraldehyde 3. K 2 Cr 2 O 7 , H 2 SO 4...
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This note was uploaded on 03/24/2008 for the course CEM 242 taught by Professor Forgot during the Fall '07 term at Michigan State University.

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Answers%20to%20PS7 - Cr O O O Me Ph HO Cr O O O Me Ph O Cr...

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