Reactions of Alkenes

By: Isman Kurniawan

Monday, July 21, 14

Electrophilic Addition
to Alkenes

Mechanism

Monday, July 21, 14

Addition of Hydrogen
Halides to Alkenes

Markovnikovs rule
Mechanism

Monday, July 21, 14

Addition of Hydrogen
Halides to Alkenes

Markovnikovs rule

Monday, July 21, 14

Addition of Hydrogen
Halides to Alkenes
Markovnikovs rule
The addition of proton acid to double bond
of an alkene result in a product with the acid
proton bonded to the carbon atom that
already hold the greater number of hydrogen
atoms.

Monday, July 21, 14

Exercise
Predict the major products of the following
reactions.

Monday, July 21, 14

Addition of Hydrogen
Halides to Alkenes
Free radical addition: Anti-Markovnikov
addition

Mechanism

Monday, July 21, 14

Addition of Hydrogen
Halides to Alkenes

Mechanism

Monday, July 21, 14

Addition of Hydrogen
Halides to Alkenes

Free radical addition: Anti-Markovnikov

addition

Monday, July 21, 14

Exercise
Predict the major products of the following
reactions, and propose mechanism to
support your predictions.

Monday, July 21, 14

Addition of Water:
Hydration of Alkenes
Mechanism

Monday, July 21, 14

Addition of Water:
Hydration of Alkenes
Mechanism

Monday, July 21, 14

Addition of Water:
Hydration of Alkenes
Rearrangement

Monday, July 21, 14

Exercise
Predict the products of the following
hydration reactions.

Monday, July 21, 14

Addition of Halogens
to Alkenes

Mechanism

Monday, July 21, 14

Formation of
Halohydrins
Halohydrin : an alcohol with halogen on the
adjacent carbon atom

Mechanism

Monday, July 21, 14

Formation of
Halohydrins

Mechanism

Monday, July 21, 14

Exercise
Predict the major product(s) for each

reaction. Include stereochemistry where

appropriate

Monday, July 21, 14

Catalytic Hydrogenation
of Alkenes
Mechanism using heterogeneous catalyst

Monday, July 21, 14

Epoxidation of Alkenes
Epoxide : three-membered cyclic.
An alkene is converted to an epoxide by a
peroxyacid

Monday, July 21, 14

Epoxidation of Alkenes
Mechanism

Monday, July 21, 14

Epoxidation of Alkenes
Consequence of concerted reaction

Monday, July 21, 14

Exercise
Predict the products, including

stereochemistry where appropriate, for the

m-chloroperoxybenzoic acid epoxidations
of the following alkenes

Monday, July 21, 14

Acid-Catalyzed Opening
of Epoxides
Mechanism

Monday, July 21, 14

Acid-Catalyzed Opening
of Epoxides
Mechanism

Monday, July 21, 14

Syn Hydroxylation of
Alkenes
Mechanism of Permanganate hydroxylation

Monday, July 21, 14

Exercise
Predict the major products of the following
reactions, including stereochemistry.

Monday, July 21, 14

Oxidative Cleavage of
Alkenes
Cleavage by permanganate
condition: the solution is warm or acidic
or too concentrated

Monday, July 21, 14

Oxidative Cleavage of
Alkenes
Ozonolysis

Monday, July 21, 14

Exercise
Give structures of the alkenes that would

give the following products upon ozonolysis

reduction

Monday, July 21, 14

Oxidative Cleavage of
Alkenes
Comparison of permanganate cleavage and
ozonolysis

Monday, July 21, 14