MT2_Wi05 - NU, Winter 2005, MT2 Chem 210-2 2 1. (20 pts)...

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NU, Winter 2005, MT2 Chem 210-2 2 1. (20 pts) For a, gives the IUPAC name of the structure shown, noting the correct stereochemistry in the name. For b-e, complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate any stereochemistry when relevant. If there is no reaction, say so. a) Br O 2 N b) c) O O HO HO OH OH d) e) HN O O HN O O O O
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NU, Winter 2005, MT2 Chem 210-2 3 2. (20 pts) Draw the π molecular orbitals of 1,3,5-hexatrienyl dianion, complete with all the lobes and order them on the energy scales below. Fill the electron into the molecular orbital levels and show the HOMO and the LUMO of this molecule. Relative to 1,3,5-hextriene, how stable do you expect 1,3,5- hextrienyl dianion to be? Use this information and any necessary diagram to determine if the thermal [6 + 6] reaction between cis , cis , cis -1,3,5-hexatriene and cis , cis , cis -1,3,5-hexatriene can occur. What about the thermal [6 + 4] reaction between cis , cis , cis -1,3,5-hexatriene and furan? You can buy the structure of any of these molecules from the instructor for 1 pt each if you don’t know what they are.
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This note was uploaded on 06/12/2008 for the course CHEM 210-2 taught by Professor Coddens during the Winter '08 term at Northwestern.

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MT2_Wi05 - NU, Winter 2005, MT2 Chem 210-2 2 1. (20 pts)...

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