FinalA-2006

FinalA-2006 - Stoltz Ch 41c Final Exam S 2006 1 Chem 41c...

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Unformatted text preview: Stoltz Ch 41c Final Exam S 2006 1 Chem 41c Final Exam Stoltz, Spring 2006, June 5, 2006 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 17 pages in this exam packet. The Exam is due by Friday June 9, 2006 by 5 PM. Name: _________________________________________ Stoltz Ch 41c Final Exam S 2006 2 Stoltz Ch 41c Final Exam S 2006 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 CO 2 Me NH 1. 2. H 3 O + + O CO 2 Me 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 1. MeLi 2. H 3 O + OH Me Stoltz Ch 41c Final Exam S 2006 4 d. O 1. Et 2 CuLi 2. H 3 O + O Et e. Br (PPh 3 ) 4 Pd 80 °C SnBu 3 CO 2 Me CO 2 Me f. MeO O OMe H H 1. LiAlH 4 , THF; Then H 3 O + /H 2 O 2. (COCl) 2 , DMSO, CH 2 Cl 2 ; Then Et 3 N MeO O H H H PNAS, 2004 , 101 , 12073-12078 Stoltz Ch 41c Final Exam S 2006 5 g. Cl I Pd(PPh 3 ) 4 (5 mol%) K 2 CO 3 (2 equiv) DMF, 80 °C + Cl h. H 2 N NO 2 NO 2 NaNO 2 , HCl Then, CuCl Cl NO 2 NO 2 Can. J. Chem. 2005 , 83 , 213-219 i. O N O O 1. LDA, THF, -78 °C 2. Br O N O O Ph 5 point bonus: what is the structure of LDA? N Li Ph j. O O 1. MeMgBr (excess) 2. H 3 O + OH Stoltz Ch 41c Final Exam S 2006 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. 1. H 3 O + Cl – 2. Raney Nickel HS SH H H O O H H H O H O O O O (maybe Clemmenson...not Wolf Kischner) b. O N O Me 1. DIBAL, THF 2. H 3 O + O H c. O Cl O N H N Et 3 N, CH 2 Cl 2 maybe DMAP d. O O O O 1. HCl (cat.) THF / H 2 O 2. NaBH 4 MeOH 3. H 3 O + O O Stoltz Ch 41c Final Exam S 2006 7 3. Design a synthesis of tetracarboxylic acid 1 starting from maleic anhydride ( 2 ) and any other materials containing 4 carbons or less. (15 points)containing 4 carbons or less....
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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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FinalA-2006 - Stoltz Ch 41c Final Exam S 2006 1 Chem 41c...

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