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UD CHEM 634 - CHEM634 EXAM

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Chem 634Professor FoxExam 3May 21, 20043 hoursYour Name___________________a1. Provide reagents for the following transformations. Mechanistic detailsare not required, but be sure to indicate relative stereochemistrywhere necessary (six parts; 3 pts each). More than one step may be required.bChem 634 Exam 3 Your Name___________________May 21, 2004HHHHOHMeOOOOc1. (continued)dChem 634 Exam 3 Your Name___________________May 21, 2004HOOOe1. (continued)fChem 634 Exam 3 Your Name___________________May 21, 2004Ph HOPhOHOMeEtOEtMeS Rab2. Predict if each of the following reactions would proceed as written. If you feel that the reactionwould proceed, simply write “will proceed as written”.If you feel that the reaction would not proceed as written, provide a brief but detailed explanation, and indicate the structure of the product(s) that would be formed instead of (or in addition to) the product that is drawn (3 points each). Chem 634 Exam 3 Your Name___________________May 21, 2004OMeFe(CO)5OOMehν1)Ph SOOPhCHOPh–2) MsCl3) Na/Hgc2. (continued). dChem 634 Exam 3 Your Name___________________May 21, 2004H2N-NHTs, NaBH3CNOCO2MeCO2MeMeNaOMeOMeCO2Mee2. (continued). fChem 634 Exam 3 Your Name___________________May 21, 20041) mCPBAMe EtSPhEt MeOH2) P(OMe)3, MeOHHHHHOLiAlH4HHHHHO3. Provide a detailed arrow pushing mechanism (15 pts)Chem 634 Exam 3 Your Name___________________May 21, 2004NNHTs1) BuLi2) H+4. Provide a detailed arrow pushing mechanism (15 pts)Chem 634 Exam 3 Your Name___________________May 21, 2004OOPhOOClAlMe2OOPhOCp2Ti2 equiv5. Consider the following reactionChem 634 Exam 3 Your Name___________________May 21, 2004NEtO1) LiHMDSNHEtOLiHMDS = TMS2NLi2) H+a) Provide an arrow pushing mechanism (5 pts)b) Propose a transition state model for the transformation (7 pts)c) Based on your answer to (b), what does the relativestereochemistry of the product tell you about the stereochemistry ofthe enolization. In otherwords, do you form the E or Z enolate.Explain your answer (7 pts)Chem 634 Exam 3 Your Name___________________May 21, 20045. Propose a synthesis using any acyclic materialsNCH3MeO2COH3C(15


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UD CHEM 634 - CHEM634 EXAM

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