Chem 634Exam 1Fall 2005Prof. FoxOpen book, open notesModels are permittedNo electronic devicesName______________________________1. Provide reagents for the following transformations. More than one step may be required. Mechanistic details are not needed.aHHOHHOHbOHOONEt2cBrTMSName______________________________(5 points each)Name______________________________(5 points)(5 points each)3. Draw 3-dimensional representations of the structures belowe.g.HHHHHHaHH HHHHHbHHH2. Provide a structure for the R -group that would give the diastereoselectivity shownROMe EtO ROMe EtOHBH3K+5. Propose a multistep synthesis of C from B.4. Provide a mechanism for the formation of B from AMeOOMeMeMgBrH3O+MeMeOABMeMeOBOHMeMeMeHOCName______________________________(10 points)(15 points)6. Circle the correct product. Provide a mechanistic rationale.D HHBr Pd(0)Et3ND HHDororName______________________________(12 points)Name______________________________(6 points)(10 points)7. Consider the reaction belowEt OOAcMea. Provide an arrow pushing mechanism.Hint:1) AlCl3Et OH2) H3O+Me OMeOAcAlCl3Me OMeb. Provide a transition state model that explains the stereospecificity of the reaction(R)(S)8. Provide an arrow pushing mechanism.O OOOAcPhOH OOPh1) AlCl32) H3O+Name______________________________(17
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