Lesson Structure

1.0       Objective

1.1       Introduction

1.2       Electrophilic addition

1.2.1    Halogen addition reaction

1.2.2    Hydrohalogenation

1.2.2.1 Anti-Markovnikov addition

1.2.3    Oxymercuration reaction

1.2.3.1 Regioselectivity and stereochemistry of oxymercuration

1.3       Nucleophilic addition

1.3.1    Cyanoethylation

1.3.2    Hydro-cyano-addition

1.3.4    Epoxidation of α,β-unsaturated carbonyls

1.4       Free radical addition

1.4.1    Stereochemistry of Free radical addition of HBr

1.4.2    Free Radical Addition of Halomethanes

1.4.3    Other Free Radical Additions of Alkenes

1.5       Addition to cyclopropane ring

1.5.1    Structure and bonding in the cyclopropane ring

1.5.2    Addition reactions of cyclopropane ring

1.5.3    Mechanism of electrophilic addition to cyclopropane

1.5.4    Nucleophilic addition to cyclopropane

1.5.5    Addition of Free radicals to cyclopropane

1.6       Hydrogenation of double and triple bonds

1.7       Hydrogenation of aromatic rings

1.8       Hydroboration and related reactions

1.8.1    Properties of Borane

1.8.2    Concerted mechanism of hydroboration

1.8.3    Steric-effects also explain regiochemistry and stereochemistry of hydroboration

1.9       Michael addition

1.10     The Sharpless asymmetric epoxidation

1.10.1  Selectivity of Sharpless epoxidation

1.10.2  Mechanism of Sharpless epoxidation

1.10.3  Application of Sharpless epoxidation

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