Alkenes: Oxidation

Ozonolysis

Dihydroxylation with
OsO4
 Alkenes: Oxidation
Hydroboration oxidation
 Alkenes: Oxidation
Cold, alkaline KMnO4

acidic KMnO4
Polymerization of Alkenes
• Polymers are large molecules that
contain a large number of repeating
units of a small molecule (monomer).
• Biopolymers are typically
synthesized by organisms.
• Synthetic Polymers are made in
organic laboratories.
 Polymerization of Alkenes
Alkenes can be used as a monomeric unit
to form chain-growth polymers

styrene

polystyrene

n
Polymerization of Alkenes
 Polymerization of Alkenes
For the polymerization, electrophilic addition
reactions can be used.

BF3
F3B

In the initiation step an electrophile

(BF3) adds to the alkene to form a
carbocation intermediate.
 Polymerization of Alkenes
Subsequent propagation steps grow
the polymer until all monomers are
consumed.

+
F3B F3B
 Polymerization of Alkenes
Termination can also be accomplished
by adding a nucleophile.

Nu
F3B

n
Nu

F3B
n
 Polymerization of Alkenes
An alternative way to initiate polymerization is
starting with a radical initiator.

D
RO OR 2 RO
(hn)
radicals

The radical adds onto the alkene to form a new

radical. Propagation is accomplished via
subsequent radical additions.
R
R R
RO
RO
β-ELIMINATION REACTION

PREPARATION OF
ALKENES
Preparation of Alkenes
• β-Elimination Reactions
• Dehydrogenation of alkanes
• Dehydration of alcohols
• Dehydrohalogenation of alkyl halides
Dehydrogenation of
Alkanes
Dehydration of Alcohols
Zaitsev’s Rule
Dehydrohalogenation of
RX
ADDITION & DIELS-ALDER REACTIONS

CONJUGATED DIENES
Reaction of Conjugated
Dienes
• undergo two-step electrophilic
addition reactios just as do
simple alkenes
• 1,2 & 1,4-addition
Reaction of Conjugated
Dienes

CH2 CH CH CH3 CH2 CH CH CH3

Less Substituted Double Bond More Substituted Double Bond
(Secondary carbocation) (Primary carbocation)
Diels-Alder Reaction:
Cycloaddition
+
ADDITION, OXYDATION, & ACIDITY OF TERMINAL
ALKYNES

REACTION OF
ALKYNES
Reactivity of Alkynes
Hydrohalogenation
Hydrohalogenation
Halogenation
Hydration
 Hydration of Alkyne &
Tautomerism

Draw the ENOL tautomers of the following

ketones:
Catalytic Reduction
Oxidation
 Acidity of Terminal
Alkynes
HC CH + NH2 HC C + H3N
Acidity of Terminal
Alkynes
-FIN-