This textbook is intended for undergraduate and postgraduate students in organic chemistry.
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.
Author(s): V.K. Ahluwalia, Renu Aggarwal
Edition: 2
Publisher: Springer-Ane Books
Year: 2023
Language: English
Pages: 227
City: New Delhi
Preface to First Edition
Preface to Second Edition
Contents
About the Authors
1
Introduction
2
Nomenclature of Cycloalkanes
2.1 Monocyclic Compounds
2.2 Bicyclic Compounds
3
Synthesis of Cycloalkanes
1.3 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
9.1.3 Nomenclature
9.2 Three-membered heterocyclic compounds
9.2.1 Oxiranes (Epoxides)
9.2.3 Aziridines
9.2.4 Thiiranes
9.3 Four Membered Heterocyclic Compounds
9.3.1 Oxetanes
9.3.2 Azetidines
9.3.3 Thietane
9.4 Five Membered Heterocyclic Compounds
9.4.1 Introduction
9.4.2 Furan
9.4.3 Pyrrole
9.4.4 Thiophen
9.5 Condensed Five-Membered Heterocycles
9.5.1 Indole
9.6 Six Membered Heterocyclic Compounds
9.6.1 Pyridine
9.6.2 Pyridine N-Oxide
9.6.3 Condensed Six-membered Heterocycles
9.6.4 Isoquinoline
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
