Chem 634 Professor Fox Exam 1 March 9 2004 1 hour 15 min Your Name Chem 634 Exam 1 March 9 2004 1 Your Name Show the products of the following transformations Mechanistic details are not required but be sure to indicate relative stereochemistry where necessary four parts 5 points each O a OCH3 1 BuLi TMEDA 2 TMSCl H3C 2 equiv Bu2CuLi b CH3 O O NHPh Chem 634 Exam 1 March 9 2004 1 Your Name continued c 1 EtI Ph3P CO 4FeNa2 2 PhCH2Br O d Ph2 But SiO MeMgBr Et Me Chem 634 Exam 1 March 9 2004 Your Name 2 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 a O O mCPBA Et b Ph I O Et Et 2CuLi LiCN Me THF Ph Et Me Chem 634 Exam 1 March 9 2004 2 Your Name continued c PhCO2H 1 MeLi Me Ph 2 H Me OH d CO2 Me CH3 1 LDA 2 CO2 Me Br CH3 Chem 634 Exam 1 March 9 2004 Your Name 3 This question has two parts both of which deal with the reaction below O O O Et CO2Et Me MgBr O Me Et O Me Et 3a Provide an arrow pushing mechanism for the reaction above For this part of the problem it is not necessary to explain the stereochemical aspects of the reaction Just push the arrows and show how the final product is formed 20 points Chem 634 Exam 1 March 9 2004 Your Name 3b Provide a detailed model with explains all of the stereochemical aspects stereocenters and alkene stereochemistry 20 points O O O Et CO2Et Me MgBr O Me Et O Me Et note the stereochemistry of the following transformation when detailing your mechanism You may consider this to be general for the reactions of Grignard reagents with ketoesters O OH R MgBr R CO2Et then H CO2Et Chem 634 Exam 1 March 9 2004 Your Name 4 Outline a multistep synthesis 20 points HO2C Ph OH Ph Me Me Me Me
View Full Document
Unlocking...