Chem 634 Exam 1 Fall 2005 Prof Fox Open book open notes Models are permitted No electronic devices Name Name 1 Provide reagents for the following transformations More than one step may be required Mechanistic details are not needed 5 points each a H H OH O H H O b c O OH NEt2 TMS Br Name 2 Provide a structure for the R group that would give the diastereoselectivity shown 5 points K RO BH 3 O Me RO Et Me OH Et 3 Draw 3 dimensional representations of the structures below 5 points each e g H H H H H a H H H H H b H H H H H H Name 4 Provide a mechanism for the formation of B from A O MeMgBr Me H3O 10 points Me Me OMe O A B 15 points 5 Propose a multistep synthesis of C from B Me Me Me Me O B Me OH HO C Name 6 Circle the correct product Provide a mechanistic rationale Br H Pd 0 or 12 points or Et3 N D H D H H D Name 7 Consider the reaction below 1 AlCl3 OAc Et O R Me 2 H3O a Provide an arrow pushing mechanism Hint OAc Me O Me Et S OH 6 points AlCl3 Me O Me b Provide a transition state model that explains the stereospecificity of the reaction 10 points Name 8 Provide an arrow pushing mechanism O O 1 AlCl3 OAc O Ph 17 points OH O 2 H3O Ph O
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