Chem 634Professor FoxExam 1March 9, 20041 hour 15 minYour Name___________________O OCH31) BuLi, TMEDA2) TMSCla1. Show the products of the following transformations. Mechanistic detailsare not required, but be sure to indicate relative stereochemistrywhere necessary (four parts; 5 points each)ONHPhOCH3H3C2 equiv Bu2CuLibChem 634 Exam 1 Your Name___________________March 9, 2004(CO)4FeNa21) EtI, Ph3P2) PhCH2BrPh2(But)SiOEtOMeMeMgBrc1. (continued)dChem 634 Exam 1 Your Name___________________March 9, 2004a2. The reactions below would not proceed as indicated. 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 (5 points each). bChem 634 Exam 1 Your Name___________________March 9, 2004OOOmCPBAPh MeEt I Et2CuLi•LiCNTHFPh MeEt Etc2. (continued). dChem 634 Exam 1 Your Name___________________March 9, 2004PhCO2HPh OHMeMe1) MeLi2) H+CO2MeBrCO2MeCH3CH31) LDA2)Chem 634 Exam 1 Your Name___________________March 9, 20043. This question has two parts, both of which deal with the reaction below:3a. Provide an arrow pushing mechanism for the reaction above. For this part of theproblem, it is not necessary to explain the stereochemical aspects of the reaction. Justpush the arrows and show how the final product is formed. (20 points)OCO2EtEtMeMgBrMeEtOOOOEtMeChem 634 Exam 1 Your Name___________________March 9, 20043b. Provide a detailed model with explains all of the stereochemical aspects(stereocenters and alkene stereochemistry). (20 points)OCO2Et CO2EtR MgBrOHRnote the stereochemistry of the following transformation when detailing your mechanism. You mayconsider this to be general for the reactions of Grignard reagents with β -ketoestersthen H+OCO2EtEtMeMgBrMeEtOOOOEtMePhMePhMeHO2C MeMeOH4. Outline a multistep synthesis (20 points)Chem 634 Exam 1 Your Name___________________March 9,
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