ORGANIC CHEMISTRY

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
11
12
13
Exercise
Complete following reactions
(ignore stereoisomerism):

14
Exercise
Complete following reactions
(ignore stereoisomerism):

15
Exercise
The following diene react with Br2 in CH2Cl2
forming 8 products with various amounts.
Determine the structure of the 8 products.
(hint: stereoisomers):

16
DIELS-ALDER REACTIONS

17
 Reactivity of the dienophile is increased if 1 or
more electron-withdrawing groups are present

Partial positive charge 18

 Disregarding stereoisomers

1 product

1 product

1 product 2 products

19
20
Stereochemistry

Racemic
mixture

21
+ enantiomer

22
+ enantiomer
 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

23
24
Exercise
Compare reactivity of following compound
in Diels-Alder reaction with a dienophile:

25
Exercise
Complete following reactions
(ignore stereoisomerism):

26
Exercise
Complete following reactions and
determine all stereoisomers of major products:

27
28
Polymerizations

29