BÀI GIẢNG ORGANIC CHEMISTRY chapter6

Phan Faculty of Chemical Engineering HCMC University of Technology Office: room 211, B2 Building Phone: 38647256 ext... Chapter 6: CONJUGATED ALKADIENES A non-polar molecule... Reaction

ORGANIC CHEMISTRY

Dr Nam T S Phan Faculty of Chemical Engineering

HCMC University of Technology

Office: room 211, B2 Building Phone: 38647256 ext 5681 Email: ptsnam@hcmut.edu.vn

Chapter 6: CONJUGATED

ALKADIENES

A non-polar molecule

Reactions of isolated dienes are just like

those of alkenes

4

NOMENCLATURE OF

ALKADIENES

6

PREPARATION OF 1,3-ALKADIENE Dehydrogenations

Eliminations of unsaturated alcohols & alkyl halides

ELECTROPHILIC ADDITION

REACTIONS

9

Reaction mechanism:

11

DIELS-ALDER REACTIONS

Reactivity of the dienophile is increased if 1 or more electron-withdrawing groups are present

Partial positive charge

Stereochemistry

Racemic mixture

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

17

Polymerizations