Front Cover -- Advanced Organic Chemistry -- Copyright Page -- Contents -- Foreword -- Preface to the English Edition -- Preface to the German Edition -- Acknowledgments -- Chapter 1. Radical Substitution Reactions at the Saturated C Atom -- 1.1 Bonding and Preferred Geometries in C Radicals, Carbenium Ions and Carbanions -- 1.2 Stability of Radicals -- 1.3 Relative Rates of Analogous Radical Reactions -- 1.4 Radical Substitution Reactions: Chain Reactions -- 1.5 Radical Initiators -- 1.6 Radical Chemistry of Alkylmercury(II) Hydrides -- 1.7 Radical Halogenation of Hydrocarbons -- 1.8 Autoxidations -- 1.9 Defunctionalizations via Radical Substitution Reactions -- References -- Chapter 2. Nucleophilic Substitution Reactions at the Saturated C Atom -- 2.1 Nucleophiles and Electrophiles -- Leaving Groups -- 2.2 Good and Poor Nucleophiles -- 2.3 Leaving Groups and the Quality of Leaving Groups -- 2.4 SN2 Reactions: Kinetic and Stereochemical Analysis-Substituent Effects on Reactivity -- 2.5 SN1 Reactions: Kinetic and Stereochemical Analysis -- Substituent Effects on Reactivity -- 2.6 When Do SN Reactions at Saturated C Atoms Take Place According to the SN1 Mechanism and When Do They Take Place According to the SN2 Mechanism? -- 2.7 Unimolecular SN Reactions That Do Not Take Place via Simple Carbenium Ion Intermediates: Neighboring Group Participation -- 2.8 Preparatively Useful SN2 Reactions: Alkylations -- References -- Chapter 3. Additions to the Olefinic C=C Double Bond -- 3.1 The Concept of cis and trans Addition -- 3.2 Vocabulary of Stereochemistry and Stereoselective Synthesis I -- 3.3 Additions That Take Place Diastereoselectivity as cis Additions -- 3.4 Enantioselective cis Additions to C=C Double Bonds -- 3.5 Additions That Take Place Diastereoselectively as trans Additions (Additions via Onium Intermediates).

3.6 Additions That Take Place or Can Take Place without Stereocontrol Depending on the Mechanism -- References -- Chapter 4. β-Eliminations -- 4.1 Concepts of Elimination Reactions -- 4.2 b-Eliminations of H/Het via Cyclic Transition States -- 4.3 b-Eliminations of H/Het via Acyclic Transition States: The Mechanistic Alternatives -- 4.4 E2 Eliminations of H/Het and the E2/SN2 Competition -- 4.5 E1 Elimination of H/Het from Rtert-X and the E1/SN1 Competition -- 4.6 E1cb Eliminations -- 4.7 β-Eliminations of Het1/Het2 -- References -- Chapter 5. Substitution Reactions on Aromatic Compounds -- 5.1 Electrophilic Aromatic Substitutions via Wheland Complexes ("Ar-SE Reactions") -- 5.2 Ar-SE Reactions via Wheland Complexes: Individual Reactions -- 5.3 Electrophilic Substitution Reactions on Metallated Aromatic Compounds -- 5.4 Nucleophilic Substitution Reactions in Aryldiazonium Salts -- 5.5 Nucleophilic Substitution Reactions via Meisenheimer Complexes -- 5.6 Nucleophilic Aromatic Substitution via Arynes, cine Substitution -- References -- Chapter 6. Nucleophilic Substitution Reactions on the Carboxyl Carbon (Except through Enolates) -- 6.1 C=O-Containing Substrates and Their Reactions with Nucleophiles -- 6.2 Mechanisms, Rate Laws, and Rate of Nucleophilic Substitution Reactions at the Carboxyl Carbon -- 6.3 Activation of Carboxylic Acids and of Carboxylic Acid Derivatives -- 6.4 Selected SN Reactions of Heteroatom Nucleophiles on the Carboxyl Carbon -- 6.5 SN Reactions of Hydride Donors, Organometallics, and Heteroatom-Stabilized "Carbanions" on the Carboxyl Carbon -- References -- Chapter 7. Additions of Heteroatom Nucleophiles to Heterocumulenes. Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Follow-up Reactions -- 7.1 Additions of Heteroatom Nucleophiles to Heterocumulenes.

7.2 Additions of Heteroatom Nucleophiles to Carbonyl Compounds -- 7.3 Addition of Heteroatom Nucleophiles to Carbonyl Compounds in Combination with Subsequent SN1 Reactions: Acetalizations -- 7.4 Addition of Nitrogen Nucleophiles to Carbonyl Compounds in Combination with Subsequent E1 Eliminations: Condensation Reactions of Nitrogen Nucleophiles with Carbonyl Compounds -- References -- Chapter 8. Addition of Hydride Donors and Organometallic Compounds to Carbonyl Compounds -- 8.1 Suitable Hydride Donors and Organometallic Compounds and a Survey of the Structure of Organometallic Compounds -- 8.2 Chemoselectivity of the Addition of Hydride Donors to Carbonyl Compounds -- 8.3 Diastereoselectivity of the Addition of Hydride Donors to Carbonyl Compounds -- 8.4 Enantioselective Addition of Hydride Donors to Carbonyl Compounds -- 8.5 Addition of Organometallic Compounds to Carbonyl Compounds -- 8.6 1,4 -Additions of Organometallic Compounds to α,β-Unsaturated Ketones -- References -- Chapter 9. Reaction of Ylides with Saturated or α,β-Unsaturated Carbonyl Compounds -- 9.1 Ylides/Ylenes -- 9.2 Reactions of S Ylides with Saturated Carbonyl Compounds or with Michael Acceptors: Three-Membered Ring Formation -- 9.3 Condensation of P Ylides with Carbonyl Compounds: Wittig Reaction -- 9.4 Horner-Wadsworth-Emmons Reaction -- References -- Chapter 10. Chemistry of the Alkaline Earth Metal Enolates -- 10.1 Basic Considerations -- 10.2 Alkylation of Quantitatively Prepared Enolates and Aza-Enolates -- Chain-Elongating Syntheses of Carbonyl Compounds and Carboxylic Acid Derivatives -- 10.3 Hydroxyalkylation of Enolates with Carbonyl Compounds ("Aldol Addition"): Synthesis of β-Hydroxyketones and β-Hydroxyesters -- 10.4 Condensation of Enolates with Carbonyl Compounds: Synthesis of Michael Acceptors -- 10.5 Acylation of Enolates -- 10.6 Michael Additions of Enolates.

References -- Chapter 11. Rearrangements -- 11.1 Nomenclature of Sigmatropic Shifts -- 11.2 Molecular Origins for the Occurrence of [1,2]-Rearrangements -- 11.3 [1,2]-Rearrangements in Species with a Valence Electron Sextet -- 11.4 [1,2]-Rearrangements without the Occurrence of a Sextet Intermediate -- 11.5 Claisen Rearrangement -- References -- Chapter 12. Thermal Cycloadditions -- 12.1 Driving Force and Feasibility of One-Step [2+4 ]- and [2+2]-Cycloadditions -- 12.2 Transition State Structures of Selected One-Step [2+4 ]- and [2+2]-Cycloadditions -- 12.3 Diels-Alder Reactions -- 12.4 [2+2]-Cycloadditions with Dichloroketene -- 12.5 1,3-Dipolar Cycloadditions -- References -- Chapter 13. Transition Metal-Mediated Alkenylations, Arylations, and Alkynylations -- 13.1 Alkenylation and Arylation of Copper-Bound Organyl Groups -- 13.2 Alkenylation and Arylation of Grignard Compounds -- 13.3 Palladium-Catalyzed Alkenylation and Arylation of Organometallic Compounds -- 13.4 Alkynylation of Copper Acetylides -- 13.5 Heck Reactions -- References -- Chapter 14. Oxidations and Reductions -- 14.1 Oxidation States of Organic Chemical Compounds, Oxidation Numbers in Organic Chemical Compounds, and Organic Chemical Redox Reactions -- 14.2 Cross-References to Redox Reactions Already Discussed in Chapters 1-13 -- 14.3 Oxidations -- 14.4 Reductions -- References -- Index.