Lecture 6 - Electrophilic Addition 1,2 vs...

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1 Reading for Monday ± Chapter 16: 16.12-16.14 ± We will not be covering 16.15 Mon. 6:00-7:30 pm MAL 3092 Tues. 2:30-4:00 PM MAL 2007 Wed. 5:00-6:30 PM MAL 2001 Thurs. 9:30-10:50 AM MAL 1003 Sat. 11:00 AM-1:00 PM MAL 2007 CHEM 626 PLUS Sessions First ARIS Quiz ± Available Now ± Due at 11:59 pm on Sunday, Feb. 6 ± Two attempts; Score will be average of the two attempts. Chapter 16 Conjugation, Resonance and Dienes Conjugated Dienes (16.6) Rotation occurs around the C-C bond that joins the double bonds Two conformations: s- cis ; s- trans (s reflects the fact that the rotation is about a formally single bond) Do not confuse these with isomers! Stability of Conjugated Dienes (16.9) Electron delocalization stabilizes conjugated dienes
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2 Stability of Conjugated Dienes (16.9) The more stable a molecule, the less potential (chemical) energy it contains
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Unformatted text preview: Electrophilic Addition: 1,2- vs. 1,4-Addition (16.10) • Protonation of 1,3-dienes by H-X generates an allylic carbocation • 2 products for symmetrical dienes: 1,2- and 1,4-addition products • 4 possible products for unsymmetrical dienes Kinetic vs. Thermodynamic Products (16.11) • Relative amounts of 1,2- and 1,4-addition products strongly depend on reaction conditions Kinetic vs. Thermodynamic Products • Figure 16.7 The Diels-Alder Reaction (16.12) • Documented in 1928 by: Otto Diels and Kurt Alder • Shared the 1950 Nobel Prize in Chem. The Diels-Alder Reaction (16.12) • Concerted cycloaddition reaction between a 1,3-diene and a dienophile (usually an alkene) • Product is a 6-membered ring...
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This note was uploaded on 10/24/2011 for the course CHEMISTRY 623 taught by Professor Benson during the Spring '11 term at Kansas.

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Lecture 6 - Electrophilic Addition 1,2 vs...

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