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MICHAEL B. SMITH, PhD, is Professor in the Department of Chemistry at the University of Connecticut. He is a coauthor of the fifth and sixth editions of March's Advanced Organic Chemistry and the author of Volumes 6 –12 of the Compendium of Organic Synthetic Methods (Wiley) as well as several other monographs.
PREFACE
BIOGRAPHICAL STATEMENT
PART 1
CHAPTER 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
1K. BOND ANGLES
1.L. BOND ENERGIES
CHAPTER TWO 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. pπ-dπ BONDING. YLIDS
2.I. AROMATICITY
2.I.i. Six-Membered Rings
2.I.ii. Five, Seven, and Eight-Membered Rings
2.I.iii. Other Systems Containing Aromatic Sextets
2.J. ALTERNANT AND NONALTERNANT HYDROCARBONS
2.K. AROMATIC SYSTEMS WITH ELECTRON NUMBERS OTHER THAN SIX
2.K.i. Systems of Two Electrons
2.K.ii. Systems of Four Electrons: Antiaromaticity
2.K.iii. Systems of Eight Electrons
2.K.iv. Systems of Ten Electrons
2.K.v. Systems of More than Ten Electrons: 4n + 2 Electrons
2.K.vi. Systems of More Than Ten Electrons: 4n Electrons
2.L. OTHER AROMATIC COMPOUNDS
2.M. HYPERCONJUGATION
2.N. TAUTOMERISM
2.N.i. Keto-Enol Tautomerism
2.N.ii. Other Proton-Shift Tautomerism
2.N.iii. Valence Tautomerism
3 BONDING WEAKER THAN COVALENT
3.A. HYDROGEN BONDING
3.B. ?-? INTERACTIONS
3.C. ADDITION COMPOUNDS
3.C.i. Electron Donor-Acceptor (EDA) Complexes
3.C.ii. Crown Ether Complexes and Cryptates
3.C.iii. Inclusion Compounds
3.C.iv. Cyclodextrins
3.D. Catenanes and Rotaxanes
3.E. Cucurbit[n]uril-Based Gyroscane
4 STEREOCHEMISTRY AND CONFORMATION
4.A. OPTICAL ACTIVITY AND CHIRALITY
4.B. Dependence of Rotation on Conditions of Measurement
4.C. What Kinds of Molecules Display Optical Activity?
4.D. THE FISCHER PROJECTION
4.E. ABSOLUTE CONFIGURATION
4.E.i. THE CAHN-INGOLD-PRELOG SYSTEM
4.E.ii. METHODS OF DETERMINING CONFIGURATION
4.F. THE CAUSE OF OPTICAL ACTIVITY
4.G. MOLECULES WITH MORE THAN ONE STEREOGENIC CENTER
4.H. ASYMMETRIC SYNTHESIS
4.I. METHODS OF RESOLUTION
4.J. OPTICAL PURITY
4.K. CIS-TRANS ISOMERISM
4.K.i. Cis-Trans Isomerism Resulting from Double Bonds
4.K.ii. Cis-Trans Isomerism of Monocyclic Compounds
4.K.iii. Cis-Trans Isomerism of Fused and Bridged Ring Systems
4.L. OUT-IN ISOMERISM
4.M. ENANTIOTOPIC AND DIASTEREOTOPIC ATOMS, GROUPS, AND FACES
4.N. STEREOSPECIFIC AND STEREOSELECTIVE SYNTHESES
4.O. CONFORMATIONAL ANALYSIS
4.O.i. Conformation in Open-Chain Systems
4.O.ii. Conformation in Six-Membered Rings
4.O.iii. Conformation in Six-Membered Rings Containing Heteroatoms
4.O.iv. Conformation in Other Rings
4.P. MOLECULAR MECHANICS
4.Q. STRAIN
4.Q.i. Strain in Small Rings
4.Q.ii. Strain in Other Rings
4.Q.iii. Unsaturated Rings
4.Q.iv. Strain Due to Unavoidable Crowding
5 CARBOCATIONS, CARBANIONS, FREE RADICALS, CARBENES, AND NITRENES
5.A. CARBOCATIONS
5.A.i. Nomenclature
5.A.ii. Stability and Structure of Carbocations
5.A.iii. THE GENERATION AND FATE OF CARBOCATIONS
5.B. CARBANIONS
5.B.i. Stability and Structure
5.B.ii. THE STRUCTURE OF ORGANOMETALLIC COMPOUNDS
5.B.iii. THE GENERATION AND FATE OF CARBANIONS
5.C. FREE RADICALS
5.C.i. Stability and Structure
5.C.ii. THE GENERATION AND FATE OF FREE RADICALS
5.C.iii. RADICAL IONS
5.D. CARBENES
5.D.i. Stability and Structure
5.D.ii. THE GENERATION AND FATE OF 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
6.J.i. Identification of Products
6.J.ii. Determination of the Presence of an Intermediate
6.J.iii. The Study of Catalysis
6.J.iv. Isotopic Labeling
6.J.v. Stereochemical Evidence
6.J.vi. Kinetic Evidence
6.J.vii. Isotope Effects
7 IRRADIATION PROCESSES IN ORGANIC CHEMISTRY
7.A. PHOTOCHEMISTRY
7.A.i. Excited States and the Ground State
7.A.ii. Singlet and Triplet States: "Forbidden" Transitions
7.A.iii. Types of Excitation
7.A.iv. Nomenclature and Properties of Excited States
7.A.v. Photolytic Cleavage
7.A.vi. The Fate of the Excited Molecule: Physical Processes
7.A.vii. The Fate of the Excited Molecule: Chemical Processes
7.A.viii. The Determination of Photochemical Mechanisms
7.B. SONOCHEMISTRY
7.C. MICROWAVE CHEMISTRY
8 ACIDS AND BASES
8.A. BR?NSTED THEORY
8.A.i. Bronsted Acids
8.A.ii. Bronsted Bases
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.E.i. Hard And Soft 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
9.D.i. HIGH PRESSURE
9.D.ii. WATER AND OTHER NON-ORGANIC SOLVENTS
9.D.iii. IONIC SOLVENTS
9.D.iv. SOLVENTLESS REACTIONS
PART 2
9.E. IUPAC NOMENCLATURE FOR TRANSFORMATIONS
9.E.i. Substitutions
9.E.ii. Additions
9.F. IUPAC SYSTEM FOR SYMBOLIC REPRESENTATION OF MECHANISMS
9.G. ORGANIC SYNTHESES REFERENCES
10 ALIPHATIC SUBSTITUTION, NUCLEOPHILIC AND ORGANOMETALLIC
10.A. MECHANISMS
10.A.i. The SN2 Mechanism
10.A.ii. The SN1 Mechanism
10.A.iii. Ion Pairs in the SN1 Mechanism
10.A.iv. Mixed SN1 and SN2 Mechanisms
10.B. SET Mechanisms
10.C. The Neighboring-Group Mechanism
10.C.i. Neighboring-Group Participation by π and ? Bonds: Nonclassical Carbocations
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.G.i. The Effect of Substrate Structure
10.G.ii. The Effect of the Attacking Nucleophile
10.G.iii. The Effect of the Leaving Group
10.G.iv. The Effect of the Reaction Medium
10.G.v. Phase-Transfer Catalysis
10.G.vi. Influencing Reactivity by External Means
10.G.vii. Ambident (Bidentant) Nucleophiles: Regioselectivity
10.G.viii. Ambident Substrates
10.H. REACTIONS
10.H.i. OXYGEN NUCLEOPHILES
10.H.ii. SULFUR NUCLEOPHILES
10.H.iii. NITROGEN NUCLEOPHILES
10.H.iv. HALOGEN NUCLEOPHILES
10.H.v. CARBON NUCLEOPHILES
11 AROMATIC SUBSTITUTION, ELECTROPHILIC
11.A. MECHANISMS
11.A.i. The Arenium Ion Mechanism
11.A.ii. The SE1 Mechanism
11.B. ORIENTATION AND REACTIVITY
11.B.i. Orientation and Reactivity in Monosubstituted Benzene Rings
11.B.ii. The Ortho/Para Ratio
11.B.iii. Ipso Attack
11.B.iv. Orientation in Benzene Rings With More Than One Substituent
11.B.v. Orientation in Other Ring Systems
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
11.F.i. Hydrogen as the Leaving Group in Simple Substitution Reactions
11.F.ii. HYDROGEN AS THE LEAVING GROUP IN REARRANGEMENT REACTIONS
11.F.iii. OTHER LEAVING GROUPS
12. ALIPHATIC, ALKENYL, AND ALKYNYL SUBSTITUTION, ELECTROPHILIC AND ORGANOMETALLIC
12.A. MECHANISMS
12.A.i. Bimolecular Mechanisms. SE2 and SEi
12.A.ii. THE SE1 MECHANISM
12.A.iii. Electrophilic Substitution Accompanied by Double-Bond Shifts
12.A.iv. Other Mechanisms
12.B. REACTIVITY
12.C. REACTIONS
12.C.i. Hydrogen as Leaving Group
12.C.ii. METALS AS LEAVING GROUPS
12.C.iii. HALOGEN AS LEAVING GROUP
12.C.iv. CARBON LEAVING GROUPS
12.C.v. ELECTROPHILIC SUBSTITUTION AT NITROGEN
13. AROMATIC SUBSTITUTION, NUCLEOPHILIC AND ORGANOMETALLIC
13.A. MECHANISMS
13.A.i. The SNAr Mechanism
13.A.ii. The SN1 Mechanism
13.A.iii. The Benzyne Mechanism
13.A.iv. The SRN1 Mechanism
13.A.v. Other Mechanisms
13.B. REACTIVITY
13.B.i. The Effect of Substrate Structure
13.B.ii. The Effect of the Leaving Group
13.B.iii. The Effect of the Attacking Nucleophile
13.C. REACTIONS
13.C.i. ALL LEAVING GROUPS EXCEPT HYDROGEN AND N2+
13.C.ii. HYDROGEN AS LEAVING GROUP
13.C.iii. NITROGEN AS LEAVING GROUP
13.C.iv. REARRANGEMENTS
14 SUBSTITUTION REACTIONS, RADICAL
14.A. MECHANISMS
14.A.i. Radical Mechanisms in General
14.A.ii. Free-Radical Substitution Mechanisms
14.A.iii. Mechanisms at an Aromatic Substrate
14.A.iv. Neighboring-Group Assistance in Free-Radical Reactions
14.B. REACTIVITY
14.B.i. Reactivity for Aliphatic Substrates
14.B.ii. Reactivity at a Bridgehead
14.B.iii. Reactivity in Aromatic Substrates
14.B.iv. Reactivity in the Attacking Radical
14.B.v. The Effect of Solvent on Reactivity
14.C. REACTIONS
14.C.i. HYDROGEN AS LEAVING GROUP
14.C.ii. N2 AS LEAVING GROUP
14.C.iii. METALS AS LEAVING GROUPS
14.C.iv. HALOGEN AS LEAVING GROUP
14.C.v. SULFUR AS LEAVING GROUP
14.C.vi. CARBON AS LEAVING GROUP
15 ADDITION TO CARBON-CARBON MULTIPLE BONDS
15.A. MECHANISMS
15.A.i Electrophilic Addition
15.A.ii. Nucleophilic Addition
15.A.iii. Free-Radical Addition
15.A.iv. Cyclic Mechanisms
15.B. ORIENTATION AND REACTIVITY
15.B.i. Reactivity
15.B.ii. Orientation
15.B.iii. Stereochemical Orientation
15.B.iv. Addition to Cyclopropane Rings
15.C. REACTIONS
15.C.i. Isomerization Of Double And Triple Bonds
15.C.ii. Reactions In Which Hydrogen Adds To One Side
15.C.ii. Reactions In Which Hydrogen Adds To Neither Side
15.C.iii. Cycloaddition Reactions
C16 ADDITION TO CARBON-HETERO MULTIPLE BONDS
16.A. MECHANISM AND REACTIVITY
16.A.i. Nucleophilic Substitution at an Aliphatic Trigonal Carbon. The Tetrahedral Mechanism
16.B. REACTIONS
16.B.i. Reactions In Which Hydrogen Or A Metallic Ion Adds To The Heteroatom
16.B.ii. Acyl Substitution Reactions
16.B.iii. Reactions In Which Carbon Adds To The Heteroatom
16.B.iv. Addition To Isocyanides
16.B.v. Nucleophilic Substitution At A Sulfonyl Sulfur Atom
CHAPTER 17 ELIMINATIONS
17.A. MECHANISMS AND ORIENTATION
17.A.i. The E2 Mechanism
17.A.ii. The E1 Mechanism
17.A.iii. The E1cB Mechanism
17.A.iv. The E1-E2-E1cB Spectrum
17.A.v. The E2C Mechanism
17.B. Regiochemistry of the Double Bond
17.C. Stereochemistry of the Double Bond
17.D. REACTIVITY
17.D.i. Effect of Substrate Structure
17.D.ii. Effect of the Attacking Base
17.D.iii. Effect of the Leaving Group
17.D.iv. Effect of the Medium
17.E. MECHANISMS AND ORIENTATION IN PYROLYTIC ELIMINATIONS
17.E.i. Mechanisms
17.E.ii. Orientation in Pyrolytic Eliminations
17.E.iii. 1,4 Conjugate Eliminations
17.F. REACTIONS
17.F.i. Reactions In Which C=C And C?C Bonds Are Formed
17.F.ii. Fragmentations
17.F.iii. Reactions In Which C?N Or C=N Bonds Are Formed
17.F.iv. Reactions In Which C=O Bonds Are Formed
17.F.v. Reactions In Which N=N Bonds Are Formed
17.F.vi. Extrusion Reactions
CHAPTER 18 REARRANGEMENTS
18.A. MECHANISMS
18.A.i. Nucleophilic Rearrangements
18.A.ii. The Actual Nature of the Migration
18.A.iii. Migratory Aptitudes
18.A.iv. Memory Effects
18.B. Longer Nucleophilic Rearrangements
18.C. Free-Radical Rearrangements
18.D. Carbene Rearrangements
18.E. Electrophilic Rearrangements
18.F. REACTIONS
18.F.i. 1,2-Rearrangements
18.F.ii. Non-1,2 Rearrangements
CHAPTER 19 OXIDATIONS AND REDUCTIONS
19.A. MECHANISMS
19.B. REACTIONS
19.B.i. Oxidations
19.B.ii. Reductions
APPENDIX A THE LITERATURE OF ORGANIC CHEMISTRY
A. PRIMARY SOURCES
A.i. Journals
A.ii. Patents
B. SECONDARY SOURCES
B.i. Listings of Titles
B.ii. Abstracts
B.iii. Beilstein
B.iv. Tables of Information
C. REVIEWS
C.i. Annual Reviews
C.ii. Awareness Services
C.iii. General Treatises
C.iv. Monographs and Treatises on Specific Areas
C.v. Textbooks
C.vi. Other Books
D. LITERATURE SEARCHING
D.i. Literature Searching Using Printed Materials
D.ii. Literature Searching Online
D.iii. Sci-Finder - the CAS database
D.iv. Science Citation Index
D.v. How to Locate Journal Articles
D.vi. REAXYS
APPENDIX B
CLASSIFICATION OF REACTIONS BY TYPE OF COMPOUNDS SYNTHESIZED
AUTHOR INDEX
INDEX
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