MT2_Wi03 - NU, Winter 2003 Midterm 2 Nguyen 2 1. (20 pts)...

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NU, Winter 2003 2 1. (20 pts) Complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. a) + OH OH Br Br b) c) O heat a compound containing 10 C atoms d) O O O O O O e) 1) MeO(O)C-CC-C(O)OMe 2) O 3 excess 3) Me 2 S excess 4) NaBH4, excess 5) mild acidic work up f
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NU, Winter 2003 3 2. (16 pts) Use the polygon rule, order the π molecular orbitals of planar 1,3,5,7-cyclononatetraenyl cation and planar 1,3-cyclobutadienyl dianion and order them on the energy scales below. Fill the electron into the molecular orbital levels and show the HOMO and the LUMO of both of these molecules. Use this information and any necessary diagram to determine if each of these molecule is aromatic, antiaromatic, or neither. (You can buy the structures of any (or all) of these molecules from the instructor for 3 pts each if you don’t know what they are.) planar 1,3,5,7-cyclononatetraenyl cation planar 1,3-cyclobutadienyl dianion E E
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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_Wi03 - NU, Winter 2003 Midterm 2 Nguyen 2 1. (20 pts)...

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