March's Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 7ed

Author : Michael B. Smith
Price : Rs 949.00
ISBN 13 : 9788126556588
ISBN 10 : 8126556587
Pages : 2076
Type : Paperbound



The new, revised and updated edition clearly explains the theories and examples of organic chemistry, providing the most comprehensive resource about organic chemistry available. Readers are guided on planning and execution of multi-step synthetic reactions, with detailed descriptions of all the reactions. The first five chapters deal with the structure of organic compounds and discuss important organic chemistry bonds, fundamental principles of conformation, and stereochemistry of organic molecules and reactive intermediates in organic chemistry. Chapters 6 to 9 are concerned with general principles of mechanism in organic chemistry, including acids and bases, photochemistry, sonochemistry and microwave irradiation and finally the relationship between structure and reactivity. The last 10 chapters cover the nature and the scope of organic reactions and their mechanisms.



Common Abbreviations

Biographical Statement


Part I Introduction

1. Localized Chemical Bonding

1.A. Covalent Bonding

1.B. Multiple Valence

1.C. Hybridization

1.D. Multiple Bonds  

1.E. Photoelectron Spectroscopy

1.F. Electronic Structures of Molecules

1.G. Electronegativity

1.H. Dipole Moment

1.I. Inductive and Field Effects

1.J. Bond Distances

1.K. Bond Angles

1.L. Bond Energies


2. Delocalized Chemical Bonding

2.A. Molecular Orbitals

2.B. Bond Energies and Distances in Compounds Containing Delocalized Bonds

2.C. Molecules that have Delocalized Bonds

2.D. Cross-Conjugation

2.E. The Rules of Resonance

2.F. The Resonance Effect

2.G. Steric Inhibition of Resonance and the Influences of Strain

2.H. pp-dp Bonding. Ylids

2.I. Aromaticity

2.J. Alternant and Nonalternant Hydrocarbons

2.K. Aromatic Systems with Electron Numbers other than Six

2.L. Other Aromatic Compounds

2.M. Hyperconjugation

2.N. Tautomerism


3. Bonding Weaker Than Covalent

3.A. Hydrogen Bonding

3.B. p-p Interactions

3.C. Addition Compounds

3.D. Catenanes and Rotaxanes

3.E. Cucurbit[n]Uril-Based Gyroscane


4. Stereochemistry and Conformation

4.A. Optical Activity and Chirality

4.B. What Kinds of Molecules Display Optical Activity?

4.C. The Fischer Projection

4.D. Absolute Configuration

4.E. The Cause of Optical Activity

4.F. Molecules with more than One Stereogenic Center

4.G. Asymmetric Synthesis

4.H. Methods of Resolution

4.I. Optical Purity

4.J. cis--trans Isomerism

4.K. Out-In Isomerism

4.L. Enantiotopic and Diastereotopic Atoms, Groups and Faces

4.M. Stereospecific and Stereoselective Syntheses

4.N. Conformational Analysis

4.O. Molecular Mechanics

4.P. Strain


5. Carbocations, Carbanions, Free Radicals, Carbenes and Nitrenes

5.A. Carbocations

5.B. Carbanions

5.C. Free Radicals

5.D. Carbenes

5.E. Nitrenes


6. Mechanisms and Methods of Determining them

6.A. Types of Mechanism

6.B. Types of Reaction

6.C. Thermodynamic Requirements for Reaction

6.D. Kinetic Requirements for Reaction

6.E. The Baldwin Rules for Ring Closure

6.F. Kinetic and Thermodynamic Control

6.G. The Hammond Postulate

6.H. Microscopic Reversibility

6.I. Marcus Theory

6.J. Methods of Determining Mechanisms


7. Irradiation Processes in Organic Chemistry

7.A. Photochemistry

7.B. Sonochemistry

7.C. Microwave Chemistry


8. Acids and Bases

8.A. Brønsted Theory

8.B. The Mechanism of Proton-Transfer Reactions

8.C. Measurements of Solvent Acidity

8.D. Acid and Base Catalysis

8.E. Lewis Acids and Bases

8.F. The Effects of Structure on the Strengths of Acids and Bases

8.G. The Effects of the Medium on Acid and Base Strength


9. Effects of Structure and Medium on Reactivity

9.A. Resonance and Field Effects

9.B. Steric Effects

9.C. Quantitative Treatments of the Effect of Structure on Reactivity

9.D. Effect of Medium on Reactivity and Rate


Part II Introduction

10. Aliphatic Substitution, Nucleophilic and Organometallic

10.A. Mechanisms

10.B. SET Mechanisms

10.C. The Neighboring-Group Mechanism

10.D. The SNi Mechanism

10.E. Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements

10.F. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism

10.G. Reactivity

10.H. Reactions  


11. Aromatic Substitution, Electrophilic

11.A. Mechanisms

11.B. Orientation and Reactivity

11.C. Quantitative Treatments of Reactivity in the Substrate

11.D.A Quantitative Treatment of Reactivity of the Electrophile: The Selectivity Relationship

11.E. The Effect of the Leaving Group

11.F. Reactions


12. Aliphatic, Alkenyl and Alkynyl Substitution, Electrophilic and Organometallic

12.A. Mechanisms

12.B. Reactivity

12.C. Reactions


13. Aromatic Substitution: Nucleophilic and Organometallic

13.A. Mechanisms

13.B. Reactivity

13.C. Reactions


14. Substitution Reactions: Radical

14.A. Mechanisms

14.B. Reactivity

14.C. Reactions


15. Addition to Carbon-Carbon Multiple Bonds

15.A. Mechanisms

15.B. Orientation and Reactivity

15.C. Reactions


16. Addition to Carbon-Hetero Multiple Bonds

16.A. Mechanism and Reactivity

16.B. Reactions


17. Eliminations

17.A. Mechanisms and Orientation

17.B. Regiochemistry of the Double Bond

17.C. Stereochemistry of the Double Bond

17.D. Reactivity

17.E. Mechanisms and Orientation in Pyrolytic Eliminations

17.F. Reactions


18. Rearrangements

18.A. Mechanisms

18.B. Longer Nucleophilic Rearrangements

18.C. Free Radical Rearrangements

18.D. Carbene Rearrangements

18.E. Electrophilic Rearrangements

18.F. Reactions


19. Oxidations and Reductions

19.A. Mechanisms

19.B. Reactions

Appendix A: The Literature of Organic Chemistry

Appendix B: Classification of Reactions by Type of Compounds Synthesized



Author Index

Subject Index

Libraries -- chemistry, biochemistry, engineering, medical, health sciences (nutrition)


Synthetic Organic Chemists or medicinal chemists in Academia, Industry (pharmaceuticals, food, agrochemicals, biotech), or government (NIH, NRL, etc)


Graduate Students of organic chemistry, medicine, pharmaceuticals, polymers


Michael B. Smith is a professor in the Department of Chemistry at the University of Connecticut, Storrs, Connecticut.