Book description
Advanced Organic Chemistry: Reactions and Mechanisms covers the four types of reactions -- substitution, addition, elimination and rearrangement; the three types of reagents -- nucleophiles, electrophiles and radicals; and the two effects -- electroni
Table of contents
- Cover
- Title Page
- Contents
- Preface
- 1. Concept of Acids and Bases
- 2. Delocalized Chemical Bonding and Electronic Effects
-
3. Aliphatic Nucleophilic Substitution Reactions
- 3.1 Introduction
- 3.2 Mechanism of SN2 Reaction
- 3.3 Nucleophile in SN2 Reaction
- 3.4 Leaving Group in SN2 Reaction
- 3.5 Intermolecular versus Intramolecular Reactions
- 3.6 Mechanism of SN1 Reaction
- 3.7 Leaving Group in SN1 Reaction
- 3.8 Nucleophile in SN1 Reaction
- 3.9 Carbocation Rearrangements
- 3.10 Stereochemistry of SN2 and SN1 Reactions
- 3.11 Role of Solvent in SN2 and SN1 Reactions
- 3.12 Solvation Effect
- 3.13 Effect of Solvent on Rate of Reaction
- 3.14 Benzylic, Allylic, Vinylic and Aryl Halides
- 3.15 Competition between SN2 and SN1 Reactions
- 3.16 Mixed SN1 and SN2 Mechanism
- 3.17 Neighbouring Group Participation
- 3.18 Summary
- Problems
-
4. Elimination Reactions
- 4.1 Introduction
- 4.2 α-Elimination
- 4.3 E1 and E2 Mechanisms
- 4.4 Orientation of Double Bond
- 4.5 Role of Leaving Group
- 4.6 E2 Eliminations from Cyclohexanes
- 4.7 Regioselectivity of E2 Eliminations
- 4.8 E2 Elimination from Vinyl Halides: How to Make Alkynes
- 4.9 Anion-stabilizing Groups Allow E1cB
- 4.10 E1cB Rate Equation
- 4.11 E1cB Eliminations in Context
- 4.12 E1–E2–E1cB Spectrum
- 4.13 Pyrolytic or Thermal Eliminations
- 4.14 Summary
- Problems
-
5. Addition Reactions
- 5.1 Introduction
- 5.2 Electrophilic Addition of HX and X2 to Alkenes
- 5.3 Mechanism of Electrophilic Addition
- 5.4 Acid-catalyzed Hydrolysis of Vinyl Ethers
- 5.5 Other Electrophilic Addition Reactions to Alkenes
- 5.6 Electrophilic Addition to Alkynes
- 5.7 Nucleophilic Addition to Alkenes and Alkynes
- 5.8 Radical Addition to Alkenes
- 5.9 Diels–Alder Reaction
- 5.10 Summary
- Problems
- 6. Free Radical Reactions
-
7. Molecular Rearrangements
- 7.1 Introduction
- 7.2 Cationic Rearrangements
- 7.3 Wagner–Meerwein Rearrangement
- 7.4 Pinacol Rearrangement
- 7.5 Semipinacol Rearrangements
- 7.6 Demjanov Rearrangement
- 7.7 Baeyer–Villiger Oxidation
- 7.8 Fries Rearrangement
- 7.9 Dienone–Phenol Rearrangement
- 7.10 Rearrangement to Electron-deficient Nitrogen
- 7.11 Hofmann, Curtius, Schmidt and Lossen Rearrangements
- 7.12 Wolff Rearrangement
- 7.13 Electrophilic Rearrangements
- 7.14 Summary
- Problems
-
8. Aromatic Substitution
- 8.1 Introduction
- 8.2 Electrophilic Aromatic Substitution (SE Ar)
- 8.3 Reactivity and Orientation in Electrophilic Aromatic Substitution
- 8.4 Groups Donating Electrons by Mesomeric Effect
- 8.5 Groups Withdrawing Electrons by Mesomeric Effect
- 8.6 Groups Withdrawing Electrons by Inductive Effect
- 8.7 Groups Donating Electrons by Inductive Effect
- 8.8 Ortho/Para Ratios
- 8.9 Effects of Multiple Substitution
- 8.10 Hammett Equation
- 8.11 Nucleophilic Aromatic Substitution
- 8.12 Ipso Substitution
- 8.13 Summary
- Problems
-
9. Stereochemistry
- 9.1 Introduction
-
9.2 Simple Molecules: Hybridization, Conformation and Configuration
- 9.2.1 Hybridization: Methane
- 9.2.2 Hybridization: Ethene and Alkenes
- 9.2.3 Hybridization: Ethyne
- 9.2.4 Bonding and Anti-bonding Orbitals
- 9.2.5 Conformations: Ethane
- 9.2.6 Conformation of Propane and n-butane
- 9.2.7 Cyclohexane: Chair Conformation
- 9.2.8 Cyclohexane: Boat Corformation
- 9.2.9 Inversion of Cyclohexane
- 9.2.10 Monosubstituted Cyclohexanes
- 9.2.11 Disubstituted Cyclohexanes
- 9.3 Chiral Molecules
- 9.4 Homochiral Molecules
- 9.5 Caged Compounds with Two Stereogenic Bridgehead Carbons
- 9.6 Epimers and Nomenclature of Bicyclic Compounds
- 9.7 Separation of Enantiomers: Resolution
- 9.8 Summary
- Problems
- 10. Buckminsterfullerene (Soccer Ball, Bucky Ball)
- 11. Pericyclic Reactions
- 12. Aromaticity
- Glossary
- Notes
- Acknowledgements
- Copyright
Product information
- Title: Advanced Organic Chemistry
- Author(s):
- Release date: October 2004
- Publisher(s): Pearson India
- ISBN: 9788131785324
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