Molecular Orbitals and Organic Chemical Reactions. Student Edition

  • ID: 2175168
  • Book
  • 378 Pages
  • John Wiley and Sons Ltd
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Molecular orbital theory is used by chemists to describe the arrangement of electrons in chemical structures. It is also a theory capable of giving some insight into the forces involved in the making and breaking of chemical bonds the chemical reactions that are often the focus of an organic chemist s interest. Organic chemists with a serious interest in understanding and explaining their work usually express their ideas in molecular orbital terms, so much so that it is now an essential component of every organic chemist s skills to have some acquaintance with molecular orbital theory.

Molecular Orbitals and Organic Chemical Reactions is both a simplified account of molecular orbital theory and a review of its applications in organic chemistry; it provides a basic introduction to the subject and a wealth of illustrative examples. In this book molecular orbital theory is presented in a much simplified, and entirely non–mathematical language, accessible to every organic chemist, whether student or research worker, whether mathematically competent or not. Topics covered include:

  • Molecular Orbital Theory
  • Molecular Orbitals and the Structures of Organic Molecules
  • Chemical Reactions How Far and How Fast
  • Ionic Reactions Reactivity
  • Ionic Reactions Stereochemistry
  • Pericyclic Reactions
  • Radical Reactions
  • Photochemical Reactions

Molecular Orbitals and Organic Chemical Reactions: Student Edition serves in a sense as a second edition of the author′s influential earlier book Frontier Orbitals and Organic Chemical Reactions, but has been completely rewritten, greatly enlarging the chapters on molecular orbital theory itself, and on the effect of orbital interactions on the structures of organic molecules. There is more on the theoretical basis for the principle of hard and soft acids and bases, and a whole chapter on the stereochemistry of the fundamental organic reactions. Correlation diagrams have been added to the discussion of pericyclic chemistry, and a great deal more in that, the largest chapter. A number of new topics, both omissions from the earlier book and work that has taken place in the intervening years, are included, and there are more words of caution in discussing frontier orbital theory itself.

Molecular Orbitals and Organic Chemical Reactions: Student Edition is an invaluable textbook on this important subject for students of organic, physical organic and computational chemistry.

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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 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 Conjugation.

2.2 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 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.



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"Fleming uses nonquantitative molecular orbital theory to explain many common phenomena in organic chemistry. As such, this is a very powerful tool for students of advanced organic chemistry. Much of what is taken simply on faith or with some hand waving in sophomore organic chemistry can be readily explained with molecular orbital theory, which is usually considered too advanced for students at that level. Though this book could be used as theprimary textbook for a course solely on molecular orbitals in organic chemistry, it will more likely be used as a reference source for an advanced organic chemistry course for upper–level undergraduates or graduate students." (CHOICE, August 2010)

"The new ′Fleming′ is a must for every lecturer and every student of chemistry a fantastic book. In this new form the textbook will last for another 30 years and remain as fresh as did its predecessor!" (Angewandte Chemie International Edition March 2010)

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