Chem 634 Professor Fox Exam 2 May 4 2004 1 hour 15 min Your Name Chem 634 Exam 2 May 4 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 a 1 Me2 CuMgBr 2 b H H Br2 O Chem 634 Exam 2 May 4 2004 1 Your Name continued c 1 cat VO acac 2 tBuOOH OH 2 TMSN3 Ti OiPr 4 1 Bu2 BOTf d O EtN iPr 2 2 PhCHO Chem 634 Exam 2 May 4 2004 Your Name 2 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 5 points each a O P O 2 F3C CO2Me KHMDS 18 C 6 CO2Me O H b O O OH I2 KI NaHCO3 O H I Chem 634 Exam 2 May 4 2004 2 Your Name continued H c O d NaIO4 CH3 CN H2O rt Ph H O RuCl 3 NH2 O Ph NaH H2N OH Chem 634 Exam 2 May 4 2004 Your Name 3 The reaction below gives only one of the five products below cat Ru CH2 H H H H H H H H H H H a b Circle the correct structure Provide a detailed arrow pushing mechanism for its formation 20 pts Ru CH2 PCy3 Cl2Ru CH2 PCy3 using the abbreviation Ru is sufficient for this problem Chem 634 Exam 2 May 4 2004 Your Name 4 Provide a detailed arrow pushing mechanism 20 points OMe Me OH OH PdCl2 CO MeOH O H H Me O O H OMe Chem 634 Exam 2 May 4 2004 5 Outline a multistep synthesis using any materials with 6 carbons or less 20 points H Your Name
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