Alicyclic Chemistry

Description

It describes the synthesis and properties of cycloalkanes compounds such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane and cycloheptatriene. It further covers the chemistry of ring compounds. The book also covers the reaction mechanisms of non-benzenoid aromatic compounds including annulenes, metallocenes and azulenes. It further contains discussions on tropone, tropolones, fluxional molecules, catenanes and rotaxanes. End-of-chapter exercises such as multiple-choice questions and short answer-questions help students in self-learning. This textbook is useful for undergraduate and postgraduate students in organic chemistry. Cover Half Title Alicyclic Chemistry Copyright Preface to First Edition Preface to Secon Edition Contents About the Authors 1. Introduction 2. Nomenclature of Cycloalkanes 2.1 Monocyclic Compounds 2.2 Bicyclic Compounds 3. Synthesis of Cycloalkanes 3.1 Synthesis of Cycloalkanes 4. Properties of Cycloalkanes 4.1 Physical properties 4.2 Infrared Spectra 4.3 Ultraviolet Spectra 4.4 Nuclear Magnetic Reasonaee Spectra 4.5 Chemical properties of cycloalkanes 4.5.1 Baeyers Strain Theory 4.5.2 Limitations of Baeyer’s Strain Theory 4.5.3 Sachse-Mohr Theory of Strainless Rings 4.5.4 Relative Stabilities of Cycloalkanes 4.5.5 Heats of Combustion 4.5.6 Chemistry of Cycloalkanes 5. Chemistry of Small Rings 5.1 Cyclopropanes 5.1.1 Stability of Cyclopropanes 5.1.2 Cis-trans Isomeresm in Disubstituted Cyclopropane 5.1.3 Cyclopropanols 5.1.4 Cyclopropene 5.2 Cyclobutanes 5.2.1 Properties 6. Chemistry of Common Ring Compounds 6.1 Cyclopentanes 6.2 Cyclohexanes 6.3 Cycloheptane 6.4 Cycloheptatriene 7. Chemistry of Medium Sized and Larger Rings 7.1 Cyclooctane and its Derivatives 7.2 Civetone 7.3 Muscone 8. Conformations of Cycloalkanes 8.1 Conformations of Cyclopropane 8.2 Conformations of Cyclobutane 8.3 Conformations of Cyclopentane 8.4 Conformations of Cyclohexane 8.4.1 Axial and Equatorial Bonds in Cyclohexane 8.4.2 Conformations of Monosubstituted Cyclohexane 8.4.3 Conformations of Disubstituted Cyclohexanes 8.4.4 Cyclohexene 8.4.5 Cyclohexanone 8.4.6 Cyclohexane Structures having Boat Conformations 8.5 Conformations of Cycloheptane 8.6 Conformations of Cyclooctane 8.6.1 Conformation of Cyclodecane 8.6.2 Conformations of Fused Six-membered Rings 8.7 Cycloalkenes 8.7.1 Stereochemistry of Cycloalkenes 9. Cycloalkanes Containing an Heteroatom (Heterocyclic Compounds) 9.1 Introduction 9.1.1 Importance of Heterocyclic Compounds 9.1.2 Nomenclature 9.2 Three-membered heterocyclic compounds 9.2.1 Oxiranes (Epoxides) 9.2.1.1 Preparation 9.2.1.2 Properties 9.2.2 Aziridines 9.2.2.1 Synthesis 9.2.2.2 Properties 9.2.3 Thiiranes 9.2.3.1 Synthesis 9.2.3.2 Properties 9.3 Four Membered Heterocyclic Compounds 9.3.1 Oxetanes 9.3.1.1 Synthesis 9.3.1.2 Properties 9.3.2 Azetidines 9.3.2.1 Properties 9.3.2.2 Proporties 9.3.3 Thietane 9.3.3.1 Synthesis 9.3.3.2 Properties 9.4 Five Membered Heterocyclic Compounds 9.4.1 Introduction 9.4.2 Furan 9.4.2.1 Synthesis 9.4.2.2 Properties 9.4.3 Pyrrole 9.4.3.1 Synthesis 9.4.3.2 Properties 9.4.4 Thiophen 9.4.4.1 Synthesis 9.4.4.2 Properties 9.5 Condensed Five-Membered Heterocycles 9.5.1 Indole 9.5.1.1 Synthesis 9.5.1.2 Properties 9.6 Six Membered Heterocyclic Compounds 9.6.1 Pyridine 9.6.1.1 Introduction 9.6.1.2 Synthesis 9.6.1.3 Properties 9.6.2 Pyridine N-Oxide 9.6.3 Condensed Six-membered Heterocycles 9.6.3.1 Quinoline 9.6.3.2 Synthesis 9.6.3.3 Properties 9.6.4 Isoquinoline 9.6.4.1 Synthesis 9.6.4.2 Properties 10. Non-Benzenoid Aromatics 10.1 Introduction 10.2 Aromatic, Antiaromatic and Non-aromatic Compounds 10.2.1 Cyclobutadiene 10.2.2 Cyclopentadienyl Anion 10.3 Types of Aromatic compounds 10.3.1 Benzenoid Aromatic Compounds 10.3.2 Non-benzenoid Aromatic Compounds 10.3.3 Annulenes 10.3.4 [18] Annulene 10.3.5 Metallocenes 10.3.6 Azulenes 10.3.7 Synthesis of Azulenes 11. Bridged Rings 11.1 Introduction 11.2 Bicyclo[1,1,0]Butane 11.3 Bicyclo[1,1,1]Pentane and Bicyclo[2,1,1]Hexane 11.4 Bicyclo[2,1,0]Pentane 11.5 Bicyclo[2,2,0]Hexane 11.6 Bicyclo [2,2,0]Hexadiene 11.7 Bicyclo[2,2,1]Heptane 11.8 Adamantane 11.9 Twistane 12. The Cage Molecules 12.1 Introduction 12.2 Cubane 12.3 Prismane 13. Tropones and Tropolones 14. Fluxional Molecules 14.1 Bullvalene 15. Catenanes, Rotaxanes and Knots 15.1 Introduction 15.2 Nomenclature of catenanes and Rotaxanes 15.3 Catenanes 15.4 Rotaxanes Multiple Choice Questions Index