New Reaction Sections Correlation: 8th Edition → 9th Editions
New Features of the 9th Edition
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. 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
3. Bonding Weaker Than Covalent
3.a. Hydrogen Bonding
3.b. π-π Interactions
3.c. Addition Compounds
3.C.i. Electron Donor-Acceptor 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. Optical Purity
4.g. The Cause of Optical Activity
4.h. Molecules with more than One Stereogenic Center
4.i. Asymmetric Synthesis
4.j. Methods of Resolution
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 Grignard Reagents and Organolithium Reagents
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 2155.d. Carbenes
5.D.i. Stability and Structure
5.D.ii. The Generation and Fate of Carbenes
5.D.iii. N- Heterocyclic 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
6.k. Catalyst Development
7. Irradiation Processes and Techniques that Influence Reactions 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
7.d. Flow Chemistry
7.e. Mechanochemistry
8. Acids and Bases
8.a. Brønsted Theory
8.A.i. Brønsted Acids
8.A.ii. Brønsted 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-Soft Acids-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.e. High Pressure
9.f. Water and other Nonorganic Solvents
9.g. Ionic Liquid Solvents
9.h. Solventless Reactions

Part II Introduction
10. Aliphatic Substitution: Nucleophilic and Organometallic
10.A. Mechanisms
10.A.i. The S N 2 Mechanism
10.A.ii. The S N 1 Mechanism
10.A.iii. Ion Pairs in the S N 1 Mechanism
10.A.iv. Mixed S N 1 and S N 2 Mechanisms
10.B. Set Mechanisms
10.C. The Neighboring- Group Mechanism
10.C.i. Neighboring- Group Participation by π and σ Bonds: Nonclassical Carbocations
10.D. The S N I 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
11. Aromatic Substitution: Electrophilic
11.A. Mechanisms
11.A.i. The Arenium Ion 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
12. Aliphatic, Alkenyl, and Alkynyl Substitution: Electrophilic and Organometallic
12.A. Mechanisms
12.A.i. Bimolecular Mechanisms: S E 2 and S E I
12.A.ii. The S E 1 Mechanism
12.A.iii. Electrophilic Substitution Accompanied by Double- Bond Shifts
12.A.iv. Other Mechanisms
12.B. Reactivity
12.C. Reactions
13. Aromatic Substitution: Nucleophilic and Organometallic
13.A. Mechanisms
13.A.i. The S N Ar Mechanism
13.A.ii. The S N 1 Mechanism
13.A.iii. The Benzyne Mechanism
13.A.iv. The S RN 1 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
14. Radical Reactions
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
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.A.v. Addition to Conjugated Systems
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
16. Addition to Carbon-Heteroatom Multiple Bonds
16.A. Mechanism and Reactivity
16.A.i. Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism
16.B. Reactions
17. Elimination Reactions
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. Influence of the Leaving Group
17.D.iv. Influence of the Medium
17.E. Mechanisms and Orientation in Pyrolytic Eliminations
17.E.i. Mechanisms
17.E.ii. Orientation in Pyrolytic Eliminations
17.F. Reactions
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
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
Indexes