Final Exam Answer key S2009

Final Exam Answer - Stoltz Ch 41c Final Exam S 2009 1 Chem 41c Final Exam Stoltz Spring 2009 June 8 2009 The exam begins when you turn to page 2

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Stoltz Ch 41c Final Exam S 2009 1 Chem 41c Final Exam Stoltz, Spring 2009, June 8, 2009 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 170 points and counts for 40% of your course grade. Good luck. There are 16 pages in this exam packet. The Exam is due by Friday June 12, 2009 by 5 PM. Name: _________________________________________
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Stoltz Ch 41c Final Exam S 2009 2
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Stoltz Ch 41c Final Exam S 2009 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. 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 b. Br (PPh 3 ) 2 Pd Pd Br Ph 3 P Ph 3 P 80 °C c. O 1. LDA, THF, -78 °C 2. 3. mild H 3 O + work-up O H O OH draw all four possible stereoisomers O OH O OH O OH d. Br (PPh 3 ) 4 Pd 80 °C SnBu 3 CO 2 Me CO 2 Me e.
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Stoltz Ch 41c Final Exam S 2009 4 O OH HO SO 3 H (catalyst) excess O O in C 6 H 6 , 80 °C using a Dean-Stark apparatus f. O N O O 1. LDA, THF, -78 °C 2. Br O N O O 5 point bonus: what is the structure of LDA? N Li g. OH O 1. LiAlD 4 , Et 2 O 2. H 3 O + , H 2 O OH D D h. O O Br O Cl N H N N CH 2 Cl 2 , 0 °C O O Br O N i.
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Stoltz Ch 41c Final Exam S 2009 5 Me N O O OMe Me 1. THF 0 °C 2. H 3 O + , H 2 O MgBr O OMe j. CO 2 H HCl (0.1 equiv) MeOH, 45 °C O OMe
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Stoltz Ch 41c Final Exam S 2009 6 2. Provide reagents for the following transformations. They may be multistep processes, but should not be longer than 5 steps. (5 points each) a.
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This note was uploaded on 01/03/2012 for the course CH 41c taught by Professor List during the Fall '10 term at Caltech.

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Final Exam Answer - Stoltz Ch 41c Final Exam S 2009 1 Chem 41c Final Exam Stoltz Spring 2009 June 8 2009 The exam begins when you turn to page 2

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