Lecture 7 - enhance dienophile reactivity Reaction is...

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1 Reading for Wednesday ± Chapter 17: 17.1-17.5 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 Second ARIS Quiz ± Available Wednesday ± Due at 11:59 pm, Sunday, Feb. 13 ± Two attempts; Score will be average of the two attempts. Chapter 16 Conjugation, Resonance and Dienes 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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2 Specific Rules Governing the Diels- Alder Reaction (16.13) Electron withdrawing groups (EWGs)
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Unformatted text preview: enhance dienophile reactivity Reaction is stereospecific Diene must have s-cis conformation Cyclic dienes: endo product favored over exo product Endo vs. Exo Products (16.13) Endo product: Z group is closer to the bridge containing the newly formed double bond Exo product: Z group is closer to the other bridge (CH 2 bridge in the case of cyclopentadiene) Exo- vs. Endo- (Figure 16.11) Retrosynthetic Analysis of a Diels-Alder Product (16.14A) Locate 6-membered ring containing C=C Push electrons around ring, starting with the -bond; break and make the appropriate bonds. Retain the stereochemistry of substituents on C=C in the dienophile...
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Lecture 7 - enhance dienophile reactivity Reaction is...

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