Reactions of alkenes

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Table of Contents

Reactions of alkenes - catalytic hydrogenation

Mechanism of alkene hydrogenation

Mechanism of alkene hydrogenation

Heats of hydrogenation

Alkene stability

Reactions of alkenes

Electrophilic addition

Addition of hydrogen halides

Addition of hydrogen halides

Markovnikov’s rule

Markovnikov’s rule

Markovnikov addition - a regiospecific reaction

HBr - the peroxide effect

Addition of sulfuric acid

Hydration

The mechanism of the addition

An example

Orientation

Orientation

A more general “rule”

A more general “rule”

Carbocation rearrangements

Addition of halogens

Mechanism of X2 addition

Mechanism of X2 addition

Stereoselective reactions

syn and anti addition

Bromine addition - an anti addition

How can we explain the anti addition?

anti addition

Anti addition but...

The bromonium ion

The bromonium ion

Halohydrin formation

Halohydrin formation

Oxymercuration

Oxymercuration

Dimerization

Free radical addition reactions

ionic vs radical addition

Hydroboration

Hydroboration

Hydroboration

Hydroboration - the mechanism

Hydroboration - the mechanism

Hydroboration - the mechanism

Hydroxylation

Ozonolysis

Ozonolysis

KMnO4 oxidation

Problems

CHEM 16X Home Page | Faculté Saint-Jean | University of Alberta | Chemistry Department

This page is maintained by Dr. Ed Blackburn (Ed.Blackburn@UAlberta.CA), course instructor.

Updated July 3, 2000