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PS6Fa09 - the right Show the products of all the reaction...

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1 Advanced Organic Chemistry: Synthesis Name:_____________________________ CHEM 311/511 Problem Set #6 Due: Tuesday, November 17, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete ten of the fourteen boxes and graduate students must complete all fourteen. (10 pts.) a) H H R' R OAc AcO O N B O H Ph Ph Me 1) 2) Ac 2 O, Et 3 N, DMAP, CH 2 Cl 2 , BH 3 -THF THF, 0 o C b) TBSO TBSO O NEt 2 1) t-BuLi, Et 2 O 2) I-Cl c) Br OH 1) t-BuLi (2.5 eq) 2) H O O O d) B H 1) 2) Br , Pd(PPh 3 ) 4 NaOH OH OH O
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2 e) O Br Br TBSO RO O Br TBSO RO O P O O (F 3 CH 2 CO) 2 OMe KHMDS f) 1) t-BuLi, -78 o C 2) O O O O O O OH O O O OCH 3 O g) I Br Br O Br O SiMe 3 Bu 3 Sn Pd(PPh 3 ) 4 h) O O NC CO 2 Et MeO OMe O O NC MeO OMe
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3 2. Syntheses questions. Provide a series of reaction steps to transform the molecule on the left to the product on
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Unformatted text preview: the right. Show the products of all the reaction steps. Undergraduates choose two questions and graduate students do all three. (5 pts.) a) O CN b) O O c) I O 4 3. Mechanism question. Provide a reasonable mechanism for the following reaction. Label the type of reaction occurring in each step of the mechanism. Determine the oxidation state and the number of valence electrons on the transition metal in the intermediate complexes. (5 pts.) I Br (HO) 2 B Pd(PPh 3 ) 2 Cl 2 (3 mol%) , CO, K 2 CO 3 Br O...
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