FinalA-2005 - Stoltz Ch 41c Final Exam S 2005 1 Chem 41c...

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Stoltz Ch 41c Final Exam S 2005 1 Chem 41c Final Exam Stoltz, Spring 2005, June 6, 2005 The exam begins when you turn to page 2. You have 4 hours to complete the exam. This is a closed note and closed book exam with no collaboration. You may use the periodic table on the last page of this packet. You may not use any other materials. The exam has a total of 180 points and counts for 40% of your course grade. Good luck. There are XX pages in this exam packet. Name: _________________________________________
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Stoltz Ch 41c Final Exam S 2005 2
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Stoltz Ch 41c Final Exam S 2005 3 1. Predict the major non-volatile products (if any) of the following reactions or sequences. Clearly mark your answers by placing a box around the compound that you believe to be the major product. (5 points each). a. O O 1. NaOH, MeOH, H 2 O 2. DMSO, CH 2 Cl 2 , -78 °C 3. Et 3 N, -78°C 23 °C 4. NaHCO 3 work-up O Cl Cl O O O O (±)- (±)- hint: one racemic non volitile product is formed b. H 3 C H 3 C Pd D H Cl Ph 3 P 80 °C H 3 C H 3 C Pd D H Cl Ph 3 P or D c. O O OMe 1. NaH 2. n -BuLi 3. 4. H 3 O + (workup) Br O O OMe
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Stoltz Ch 41c Final Exam S 2005 4 d. Br MeO OMe CO 2 H 1. 2. Et 2 NH O Cl Br MeO OMe O NEt 2 e. Br (PPh 3 ) 4 Pd 80 °C SnBu 3 CO 2 Me CO 2 Me f. NaBH 4 EtOH, CH 2 Cl 2 23 °C, 1 h O OH OH 2 major products
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Stoltz Ch 41c Final Exam S 2005 5 g. HNO 3 , H 2 SO 4 NO 2 NO 2 NO 2 NO 2 NO 2 NO 2 and/or major minor h.
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