FinalA-2007

FinalA-2007 - Stoltz Ch 41c Final Exam S 2007 1 Chem 41c...

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Unformatted text preview: Stoltz Ch 41c Final Exam S 2007 1 Chem 41c Final Exam Stoltz, Spring 2007, June 4, 2007 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 200 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 8, 2006 by 5 PM. Name: _________________________________________ Stoltz Ch 41c Final Exam S 2007 2 Stoltz Ch 41c Final Exam S 2007 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, -78C 23 C 4. NaHCO 3 work-up O Cl Cl O O O O ()- ()- hint: one racemic non volitile product is formed b. Pd H D Cl Ph 3 P 80 C Pd H D Cl Ph 3 P or H c. O O OMe 1. NaH 2. n-BuLi 3. 4. H 3 O + (workup) Br O O OMe Stoltz Ch 41c Final Exam S 2007 4 d. O 1. MeLi 2. H 3 O + OH Me e. O OH cat. H 2 SO 4 MeOH, reflux O OMe f. O CO 2 Me NH 1. 2. H 3 O + + O CO 2 Me Stoltz Ch 41c Final Exam S 2007 5 g. Br O Cl N H Et 3 N CH 2 Cl 2 , 0 C Br O N Bu 3 Sn SnBu 3 h. O H N CHO F Me 2 NH, AcOH NaBH 3 CN O H N F N i. 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 j. O O 1. MeMgBr (excess) 2. H 3 O + OH Stoltz Ch 41c Final Exam S 2007 6 2. Provide reagents for the following transformations. They may be multistep processes, but should not be longer than 5 steps. longer than 5 steps....
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FinalA-2007 - Stoltz Ch 41c Final Exam S 2007 1 Chem 41c...

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