OQ2_Wi03 - NU Winter 2003 Quiz 2 2 1(16 pts Complete each...

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NU, Winter 2003, Quiz 2 2 1. (16 pts) Complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. Your answers should be consistent with any stereochemistry that the reaction may produce/require. i. Br 1) MeSH, NaH 2) MeI ii. 1) excess HI, heat 2) 2 NaCCH 3) Lindlar’s cat., H 2 4) CH 2 I 2 , Zn, CuCl O iii. iv. O F F Br 2. a. (8 pts) Propose mechanisms for the following reaction using the curved arrow formalism. Provide all proton transfer steps. HOTs (a strong acid), cat. THF (solvent), heat
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3 b. (10 pts) Draw the π molecular orbitals of 1,3,5,7-octatetraene 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. You can buy the structure of this molecule from the instructor for 1 pt if you don’t know what it is. 1,3,5,7-octatetraene
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OQ2_Wi03 - NU Winter 2003 Quiz 2 2 1(16 pts Complete each...

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