Chapter 6: CONJUGATED ALKADIENES

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Reactions of isolated dienes are just like those of alkenes. Reactivity of the dienophile is increased if 1 or more electron-withdrawing groups are present. In order to participate in a Diels-Alder reaction, the diene must be in an s-cis conformation.

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Nội dung Text: Chapter 6: CONJUGATED ALKADIENES

ORGANIC CHEMISTRY Dr Nam T. S. Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 8647256 ext. 5681 Email: ptsnam@hcmut.edu.vn 1
Chapter 6: CONJUGATED ALKADIENES A non-polar molecule 2
Reactions of isolated dienes are just like those of alkenes 3
4
NOMENCLATURE OF ALKADIENES 5
6
PREPARATION OF 1,3-ALKADIENE Dehydrogenations Eliminations of unsaturated alcohols & alkyl halides 7
ELECTROPHILIC ADDITION REACTIONS 8
9
Reaction mechanism: 10
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DIELS-ALDER REACTIONS 13
Reactivity of the dienophile is increased if 1 or more electron-withdrawing groups are present Partial positive charge 14
Stereochemistry Racemic mixture 15
In order to participate in a Diels-Alder reaction, the diene must be in an s-cis conformation C1 & C4 are too far apart to react with the dienophile 16
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Polymerizations 18