Diene: A diene is an unsaturated hydrocarbon containing two double bonds between carbon

atoms. Dienes are of three types:

Isolated diene: these are the dienes in which the double bonds are separated by more than
one single bond.

Conjugated diene: these are the dienes in which the double bonds are separated by one
single bond.

Cumulated diene: these are the dienes in which the double bonds are adjacent to each other.

Preparation of conjugated diene

Diels- Alder reaction: The Diels-Alder reaction is an important organic chemical reaction
where the reactants include a substituted alkene and a conjugated diene. This substituted
alkene is commonly referred to as a dienophile. This reaction gives rise to a substituted
derivative of cyclohexene. This reaction was discovered by the German chemists Otto Diels
and Kurt Alder in the year 1928, for which they received the Nobel Prize in Chemistry in
the year 1950. The Diels-Alder reaction can be used to form six-membered rings since there
is a simultaneous construction of two new carbon-carbon bonds.

Reactions of conjugated dienes

Addition of hydrogen halides • Dienes are treated with hydrogen halides to undergoes 1,2
and 1,4 addition.

Addition of halogens: Dienes are treated with halogen to undergoes 1,2 and 1,4 addition.
Addition of water: 1,3 butadiene reacts with water in the presence of H2SO4 to give a
mixture of 1,2 and 1,4 addition products.

Addition of hydrogen: • Dienes are treated with hydrogen hydrogen to undergoes 1,2 and
1,4 addition.
Polymerization: 1,3 butadiene polymerizes in the presence of peroxide to give polybutadiene

Free radical addition of conjugated diene: Dienes also undergoes free radical chain
reaction to form 1,4 addition product.
Allylic rearrangement • Allylic compounds are those which have a functional group on a
carbon atom α to an olefinic bond. Allylic compounds undergo acid or base catalyzed
migration to form new compound.

Stability of conjugated diene: Conjugated dienes are more stable than isolated dienes,
because conjugated diene shows resonance stabilization effect but isolated dienes does not
shows resonance stabilization.