Lecture 8 - Lecture 8 Organic Chemistry I Prof. Jonathan L....

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Organic Chemistry I 310/318M Pre-Health Professionals Unique numbers: 54410, 54435, 54440, 54445, and 54655 Prof. Jonathan L. Sessler Lecture 8 Note: Homework 2 will be due on the 24th, not this Wednesday. Note: Prof. Sessler’s office hours will end at 2:30 pm today. Note: Recitation after class today is in Wel 2.308. Note: There is also TIPS tutoring from 7-9 pm tonight.
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Complex Multi-atom π Systems Last Time we did simple π -bonds. Now for something a bit more challenging… Note: This material is not treated in Chapter 1 of your text. So, pay careful attention to this lecture and notes, please!
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Rules for More Complex Orbital Systems (These are Also Applicable to Simpler Systems) 1. Draw Lewis dot structure(s); count total number of electrons accounting, as needed, for net molecular charge. 2. Assign hybridization to each non-hydrogen atom. Use the following for atoms with 4 or more valence electrons (C + and B, with 3 valence electrons are usually sp 2 hybridized): i. Single bonds to all bound atoms: sp 3 ii. More than a single bond to at least one bound atom: sp 2 iii. More than a double bond to at least one bound atom: sp
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3. Using the hybrid orbitals but not left over p z and/or p y orbitals, if any, figure out (lowest energy) σ system. Put in 2e - per atom-atom σ interaction; these are represent single bonds. Note: It is generally good to label these interactions and, to the extent your artistic talents allow, show the three dimensional shape of each non- hydrogen atom component. 4. Determine the number of lone pair electrons. Lone pairs that exist as lone pairs in all resonance contributors are “real lone pairs”; draw them in as part of the σ skeleton. 5. “Sometimes lone pairs” (i.e., those that exist as lone pairs in only some of the resonance contributors) belong to the π system. “Save” these electrons to fill into the π “energy ladder” discussed on the next slide.
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6. Add any leftover p z and p y orbitals that can interact in and out of phase to generate the π orbital “energy ladder” of orbitals.
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This note was uploaded on 09/17/2008 for the course CH 310M taught by Professor Iverson during the Spring '05 term at University of Texas at Austin.

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Lecture 8 - Lecture 8 Organic Chemistry I Prof. Jonathan L....

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