2006 Organic Chemistry CHE230-001 EXAM 3 Page 2 of 7 1. (10 pts.)HCl++CHHClH+Cl a. Explain why addition of HCl does not occur by this mechanism (above). _____________________________________________ _____________________________________________ 2. OHSOOHNa+OSOO+Na+only productoptically pureABCHH a. (5 pts.) What is the mechanism of this reaction? Just give a name. _________________________ b. (5 pts.) Draw a chiral optically pure elimination product of 2A. c. (5 pts.) Draw an achiral elimination product of 2A. b. c.2006 Organic Chemistry CHE230-001 EXAM 3 Page 3 of 7 3. 3AHHOH (10 pts) Suggest a hydrocarbon starting material (only containing hydrogen and carbon atoms) and suggest reaction conditions to make a racemic mixture of trans-2-methylcyclohexanol. Draw your reaction below. Use the reaction arrow provided. As a head start. 1)your reactant3Ayour reagents 4. (10 pts.) Draw a mechanism for the following transformation. Number the carbon atoms to help you keep track of the reaction. What must the last intermediate be? What must the first intermediate be? Use the back of this page if you need more space. HOHH3O(+)Cl(-)H2OOHHO+opticallypureracemic1:12006 Organic Chemistry CHE230-001 EXAM 3 Page 4 of 7 5. (10 pts.) Draw an energy-versus-reaction progress diagram for an exothermic E2 reaction. Ereaction progress 6. (10 pts.) Below draw the polymer produced when isobutylene polymerizes under acid catalysis. You can include 3 or 4 monomer units in the polymer. (isobutylene)2006 Organic Chemistry CHE230-001 EXAM 3 Page 5 of 7 7. (10 pts.) Predict the product. It has six 13C NMR signals. OH(+)H3COH 8. (15 pts) BrBr?abc a. Give reagents a. ________________________________________________________________________ b. Give reagents b. ________________________________________________________________________ c. Draw starting molecule c. ________________________________________________________________________ 9. Explain why hydrogenation (alkenes to alkanes) is exothermic.
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