PS3Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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1 Advanced Organic Chemistry: Synthesis Name:_ Elizabeth Blackburn ________ CHEM 311/511 Problem Set #3 Due: Thursday October 1, 2009 1. Provide the necessary information, products or reagents, to complete the following reactions. Undergraduates must complete four of the five boxes and graduate students must complete all five. (6 pts.) a) b) Ph O + (EtO) 2 P O CN NaH, THF Ph CN E. J. Corey et al. JOC 1975, 40, 127. O MgBr 1) , CuI 2) BrCH 2 CO 2 Et O EtO 2 C OH HO p-TsOH EtO 2 C O O O O TsO 1) LiAlH 4 , Et 2 O 2) TsCl, pyridine K. C. Nicolaou et al. Chem. Commun. 1979, 1119. c) N O OEt O O OEt 1) LDA (2.5 eq.), TMEDA 2) N O O O OEt N. Narasimhan et al. JOC 1983, 48, 3945. (47%) 2. Mechanism questions. Choose one question (both undergraduates and graduate students). Two bonus points will be awarded for a second correct answer. (6 pts.) a) Vinyltriphenylphosphonium halides are Wittig reagents that have been successfully applied in cyclization reactions such as the ones shown below. Suggest a mechanism for these cyclization reactions.
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This note was uploaded on 02/22/2011 for the course CHEM 311 taught by Professor Johnson during the Spring '11 term at SUNY Geneseo.

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PS3Fa09ans - Advanced Organic Chemistry: Synthesis CHEM...

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