Molecular Orbitals and Organic Chemical Reactions, Student Edition

1 Molecular Orbital Theory.

1.1 The Atomic Orbitals of a Hydrogen Atom. 

1.2 Molecules made from Hydrogen Atoms.

1.3 C—H and C—C Bonds.

1.4 Conjugation—Hückel Theory.

1.5 Aromaticity.

1.6 Strained σ Bonds—Cyclopropanes and Cyclobutanes.

1.7 Heteronuclear Bonds, C—M, C—X and C=O.

1.8 The Tau Bond Model.

1.9 Spectroscopic Methods.

1.10 Exercises.

2 The Structures of Organic Molecules. 

2.1 The Effects of π Conjugation.

2.2 σ Conjugation—Hyperconjugation.

2.3 The Configurations and Conformations of Molecules.

2.4 Other Noncovalent Interactions.

2.5 Exercises.

3 Chemical Reactions—How Far and How Fast.

3.1 Factors Affecting the Position of an Equilibrium.

3.2 The Principle of Hard and Soft Acids and Bases (HSAB).

3.3 Transition Structures.

3.4 The Perturbation Theory of Reactivity.

3.5 The Salem-Klopman Equation.

3.6 Hard and Soft Nucleophiles and Electrophiles.

3.7 Other Factors Affecting Chemical Reactivity.

4 Ionic Reactions—Reactivity.

4.1 Single Electron Transfer (SET) in Ionic Reactions.

4.2 Nucleophilicity.

4.3 Ambident Nucleophiles.

4.4 Electrophilicity.

4.5 Ambident Electrophiles.

4.6 Carbenes.

4.7 Exercises.

5 Ionic Reactions—Stereochemistry.

5.1 The Stereochemistry of the Fundamental Organic Reactions.

5.2 Diastereoselectivity.

5.3 Exercises.

6 Thermal Pericyclic Reactions.

6.1 The Four Classes of Pericyclic Reactions.

6.2 Evidence for the Concertedness of Bond Making and Breaking.

6.3 Symmetry-Allowed and Symmetry-Forbidden Reactions.

6.4 Explanations for the Woodward-Hoffmann Rules.

6.5 Secondary Effects.

6.6 Exercises.

7 Radical Reactions.

7.1 Nucleophilic and Electrophilic Radicals.

7.2 The Abstraction of Hydrogen and Halogen Atoms.

7.3 The Addition of Radicals to π Bonds

7.4 Synthetic Applications of the Chemoselectivity of Radicals.

7.5 Stereochemistry in some Radical Reactions.

7.6 Ambident Radicals.

7.7 Radical Coupling.

7.8 Exercises.

8 Photochemical Reactions.

8.1 Photochemical Reactions in General.

8.2 Photochemical Ionic Reactions.

8.3 Photochemical Pericyclic Reactions and Related Stepwise Reactions.

8.4 Photochemically Induced Radical Reactions.

8.5 Chemiluminescence.

8.6 Exercises.

References.

Index.