PS1Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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Advanced Organic Chemistry: Synthesis Name:_____ Taylor Swift ___________ CHEM 311/511 Problem Set #1 Due: Friday, September 11, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. (7 pts.) a) MeO 2 C OMe Me 1) LDA 2) Me-I, HMPA CO 2 Me OMe Me Me E. J. Corey et al. JACS 1979, 101, 1608. b) OMe O OMe O KOt-Bu/t-BuOH CH 3 -I (>2 eq.) G. Stork et al. JACS 1963, 85, 3419. c) N O O Ph O 1) LiN(SiMe 3 ) 2 2) I K. Yamada et al. JOC 1996, 61, 5326 N O O Ph O d) Ph N H Boc O H N H CO 2 H H N CO 2 H CH 3 CN, 0 o C, 12 h H N CO Ph Boc-HN B. List et al. Org. Syn. 2009, 86, 11-17 2. Provide the alkylation reagents and the structures of intermediates A and B in the following scheme. Additionally, graduate students must show the mechanism of the LiAlH 4 reduction and hydrolysis reaction (a classic reaction in the repertoire of synthetic organic chemists). Undergraduates who are feeling particularly brash can earn bonus points for the mechanism. (6 pts.)
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PS1Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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