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

Info iconThis preview shows pages 1–4. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
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
Background image of page 2
3 2. Syntheses questions. Provide a series of reaction steps to transform the molecule on the left to the product on
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Background image of page 4
This is the end of the preview. Sign up to access the rest of the document.

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...
View Full Document

Page1 / 4

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

This preview shows document pages 1 - 4. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online