Week_7_PurpleBook2007

Week_7_PurpleBook2007 - 177 Frontier Molecular Orbitals of...

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Frontier Molecular Orbitals of Polyenes 1. Draw a simple representation of both the HOMO and LUMO for the following: 2. Draw resonance structures for the following ion: LUMO: Now construct the complete π molecular orbitals. Identify the HOMO, and show how the HOMO accurately represents what is seen in the resonance structures. HOMO: Week 7 177
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CO 2 Me CO 2 Me CO 2 Me CO 2 Me O HO O HO O O OMe O O Cycloadditions 1. Fill in the other reactant required for each of the following cycloadditions. Then indicate whether the reaction should take place under thermal (heat) or photochemical (light) conditions. Finally, show a curved- arrow mechanism for the indicated cyclization. OMe Ph Ph + + + Week 7 178
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CH 3 H CH 3 CH 3 CH 3 CH 3 CH 3 CH 3 7.03 CH 3 H Electrocyclic Reactions Chem S-20 1. Predict the product (include stereochemistry!) Indicate if the cyclization is CON or DISrotatory. h ν h ν (How?) but does NOT form: H H (Why not?) 2. Consider the following reaction: Week 7 179
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CH 3 D D CH 3 CO 2 OH O CH 2 CO 2 OH O 2 C Sigmatropic Rearrangements O CO 2 1. Predict the stereochemistry of the deuterated stereocenter in the following rearrangement: 2. The following transformation is carried out by an enzyme known as chorismate mutase .I t i sac ru c
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Putting It Together: FMO 1. Ozone, O 3 , is known to react with alkenes. The initial reaction between ozone and an alkene is in fact a concerted cycloaddition. a) Draw a complete Lewis structure for ozone, showing all lone pairs, formal charges, and resonance. b) Draw out all of the π -molecular orbitals of ozone. Indicate which is the HOMO and which is the LUMO. c) Show that ozone can react in a concerted, suprafacial fashion with an alkene by drawing out the symmetry- allowed transition states for both of the following interactions: A :O z on eHOMO+a l ke n eLUMO B : Ozone LUMO + alkene HOMO
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This note was uploaded on 05/01/2008 for the course CHEM 51 taught by Professor Gribble during the Spring '08 term at Dartmouth.

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Week_7_PurpleBook2007 - 177 Frontier Molecular Orbitals of...

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