PS1Fa09 - Advanced Organic Chemistry Synthesis Name CHEM...

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Unformatted text preview: Advanced Organic Chemistry: Synthesis Name:_____________________________ 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 b) OMe O OMe O c) N O O Ph O 1) LiN(SiMe 3 ) 2 2) I d) O H N H CO 2 H CH 3 CN, 0 o C, 12 h H N CO 2 H Ph Boc-HN 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.) O OEt O OEt Cl 1) LiAlH 4 2) HCl, H 2 O O Cl A alkylation reaction alkylation reaction alkylation reaction B intramolecular alkylation reaction O 3. Natural product synthesis requires an ability to recognize key bond disconnections that can create the 3....
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PS1Fa09 - Advanced Organic Chemistry Synthesis Name CHEM...

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