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Alkadienes HO
Alkadienes HO
Alkadienes HO
Nomenclature:
IUPAC system:
- use the suffix -diene to denote the
presence of two C=C bonds.
- The first C=C bond is always part of the
parent chain and takes precedence over
other substituents it is assigned the
lowest possible number.
Three Types Of Alkadienes:
Cumulenes or cumulated dienes
- dienes that have C=C bonds on adjacent carbons
(1,2-dienes).
- not an important class of compounds; generally
difficult to prepare.
- isomerize to more stable dienes.
Isolated dienes
- have C=C bonds that are separated by two or
more C-C bonds.
- The double bonds in these compounds react
independently of each other they undergo
reactions typical of alkenes but two moles of
the reagent are required to produce a
saturated product.
Conjugated dienes
- also known as 1,3-dienes
- are dienes in which the C=C are separated by
only 1 C-C bond.
- most commercially important conjugated
dienes: butadiene and 2-methyl-1,3-butadiene
or isoprene
Consider butadiene:
example:
- Conjugated Dienes: the reaction of one mole of
reagent per mole of diene always produces two
products.
example:
2. Free Radical Addition of Conjugated Dienes
example:
reaction mechanism:
(3), (4), (3), (4) ...... then termination
3. Polymerization essentially 1,4-addition
4. Ozonolysis
- All C=C bonds are attacked by ozone at
the same time ozonolysis is a useful tool for
structure elucidation. From the fragments
obtained, the positions of the C=C bonds in the
original diene molecule can be inferred.
- example:
Analysis of Alkadienes: