Last edition Elsevier Written in a concise and student-friendly way, this textbook focuses on the underlying principles of organic chemistry and provides the tools for understanding the nature of organic reactions.
Last Edition
ISBN 13: 9783110565126
Imprint: Walter de Gruyter Co
Language: English
Authors: John M. McIntosh
Pub Date: 03/2018
Pages: 321
Illus: Illustrated
Weight: 635.00 grams
Size: h 170 x 240 mm
Product Type: Softcover
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| grn 3497 |
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- • The author utilizes an integrated approach for organic chemistry, uniting in a logical manner the main reaction types and their mechanisms, compound classes and their typical reactions, organic spectroscopy and principles of structure elucidation.
- • The author utilizes an integrated approach for organic chemistry, uniting in a logical manner the main reaction types and their mechanisms, compound classes and their typical reactions, organic spectroscopy and principles of structure elucidation.
- Prof. em. John M. McIntosh, University of Windsor, Canada.
- • Cover • Title Page • Copyright • Preface • Contents
- • Part I: Fundamentals
- • 1 Introduction • 1.1 What Is Organic Chemistry? • 1.2 Bonding • 1.2.1 Ionic Bonds • 1.2.2 Covalent Bonds • 1.2.3 Molecular Orbitals • 1.2.4 Hybridization • 1.3 Three-Dimensional Properties of Carbon • 1.4 Polar Covalent Bonds • 1.5 Bonding Between Carbon Atoms • 1.6 Summary • 1.7 Problems
- • 2 The Simplest Organic Molecules – The Hydrocarbons
- • 2.1 Definitions • 2.2 Positional (or Constitutional) Isomers • 2.3 Writing Formulae • 2.4 Index of Hydrogen Deficiency • 2.5 Naming Organic Compounds • 2.6 Functional Group Concept • 2.7 Additional Definitions • 2.8 Problems
- • 3 The Shapes of Organic Molecules – Stereochemistry 1
- • 3.1 Introduction • 3.2 The Structure of Some Simple Alkanes • 3.3 Newman Projections and Conformations • 3.4 Stabilities of Conformational Isomers • 3.5 Stereoisomers • 3.6 Stereochemical Designations – The Cahn–Ingold–Prelog System • 3.7 The Sequence Rules • 3.8 Alicyclic Compounds • 3.9 Cyclohexane • 3.10 Monosubstituted Cyclohexanes • 3.11 Disubstituted Cyclohexanes • 3.12 Problems
- • 4 Reactions – Basic Principles (or Where, Why, What, How Fast, and How Far)
- • 4.1 Introduction • 4.2 Acids, Bases, and Moving Electrons • 4.3 Reversibility • 4.4 Chemical Thermodynamics (How Large is Keq) • 4.5 Kinetics (How Fast) • 4.6 Kinetic Versus Thermodynamic Control • 4.7 Molecularity of Reactions • 4.8 Nucleophiles and Electrophiles • 4.9 Inductive and Steric Effects • 4.10 Resonance Effects • 4.11 How Important is Resonance? • 4.12 Reaction Types • 4.13 Summing Up • 4.14 Problems
- • 5 Reactions of Alkanes, Alkenes, and Alkynes
- • 5.1 Introduction • 5.2 Reactions of Alkanes • 5.2.1 Oxidation • 5.2.2 Halogenation • 5.3 Electrophilic Addition to Alkenes: Our First Mechanism • 5.4 Carbocation Stabilities (Markownikov’s Rule) • 5.5 Catalysis • 5.6 Stereochemistry • 5.7 Functional Group Characterization • 5.8 Solvent Effects (Regiochemistry) • 5.9 Resonance Effects on Electrophilic Addition Reactions • 5.10 Other Reactions of Alkenes • 5.10.1 Hydroboration • 5.10.2 Hydrogenation • 5.10.3 Oxidation • 5.11 Reactions of Alkynes • 5.11.1 Hydrogenation • 5.11.2 Hydration • 5.12 Summary • 5.13 Problems
- • 6 More Stereochemistry and Another Reaction Type – Nucleophilic Substitution
- • 6.1 Introduction • 6.2 Optical Isomerism (or Chemistry with Mirrors) • 6.3 Polarimetry • 6.4 Nomenclature – The R and S System • 6.5 Fischer Projections • 6.6 Assigning Configurations from Fisher Projections • 6.7 Compounds With More Than One Chiral Center • 6.8 Meso Forms • 6.9 Resolution and Racemization • 6.10 Why Is All This Stereochemistry Important? (Subtitle:What Am I Doing Here?) • 6.11 Nucleophilic Substitution • 6.12 The Carbocation Route – SN1 Reactions • 6.13 The Concerted Route – SN2 Reactions • 6.14 Stereochemistry Again • 6.15 Which Mechanism Operates? – The Basic Factors • 6.15.1 The Carbon Center • 6.15.2 The Leaving Group • 6.15.3 The Nucleophile • 6.15.4 Solvent Effects • 6.16 Putting It All Together • 6.17 The Scope of Nucleophilic Substitution • 6.18 Reversibility and Catalysis • 6.19 Problems
- • 7 Alcohols and Ethers, Amines, and Alkyl Halides. Introduction to Carbonyl Compounds (Aldehydes, Ketones)
- • 7.1 Introduction • 7.2 Alcohols and Ethers – Chemical and Physical Properties • 7.3 Preparation of Alcohols and Ethers • 7.4 Reactions of Alcohols • 7.5 Reactions of Ethers • 7.6 Preparations of Alkyl Halides • 7.7 Amines • 7.8 Introduction to Carbonyl Groups • 7.9 The Carbonyl Group – Nucleophilic Addition • 7.10 Aldehydes and Ketones – Structure and Physical Properties • 7.11 Preparations of Aldehydes and Ketones • 7.12 Reactions of Aldehydes and Ketones • 7.12.1 General Considerations • 7.12.2 Catalysis • 7.12.3 Ketals and Acetals • 7.12.4 Protecting Groups • 7.12.5 Other Nucleophilic Addition Reactions • 7.13 The Grignard Reaction – Introduction • 7.13.1 The Grignard Reagent • 7.13.2 The Grignard Reaction • 7.13.3 Acetylide Ions as Grignard Reagents • 7.14 Reductions with Metal Hydrides • 7.15 Other Reactions of Aldehydes and Ketones • 7.15.1 Oxidation • 7.15.2 The Iodoform Test • 7.16 Introduction to Multistage Syntheses • 7.17 Problems
- • 8 More Carbonyl Chemistry – Acids and Their Derivatives
- • 8.1 Introduction • 8.2 Carboxylic Acids, Esters, Chlorides, Anhydrides, Amides (and Nitriles) • 8.3 Physical and Chemical Properties of Carboxylic Acids • 8.4 Preparations of Carboxylic Acids • 8.5 Reactions of Carboxylic Acids – Esterification • 8.6 Reactions of Esters • 8.6.1 Detergents • 8.7 Acyl Halides • 8.8 Anhydrides • 8.9 Amides • 8.10 Nitriles • 8.11 Other Reactions of Acids and Their Derivatives • 8.11.1 Grignard Reactions • 8.11.2 Reduction • 8.12 Problems
- • 9 Aromatic Compounds – Benzene and Its Derivatives. Resonance as a Force Majeure
- • 9.1 Introduction • 9.2 Aromatic Molecules, Aromaticity, and H?ckel’s Rule • 9.3 Benzene – The Prototype of Aromatic Molecules • 9.4 Reactions of Aromatic Molecules • 9.4.1 General Considerations • 9.4.2 Nitration • 9.4.3 Halogenation • 9.4.4 Acylation • 9.4.5 Alkylation • 9.5 Reversibility • 9.6 Reactions of Substituted Benzenes • 9.6.1 General Considerations • 9.6.2 Reactivities • 9.6.3 Orientations • 9.6.4 Summary • 9.6.5 Which Is It – Ortho or Para? • 9.7 Reactions of Disubstituted Compounds • 9.8 Some Special Functional Group Transformations • 9.9 Control of Reactivity • 9.10 Synthetic Problems • 9.11 The Benzylic Position • 9.12 Final Words On Reactions • 9.13 Phenols and Anilines • 9.13.1 Acidity of Phenol • 9.13.2 Diazonium Salts • 9.14 Problems
- • 10 Organic Nitrogen Compounds – Amines and Amides
- • 10.1 Introduction • 10.2 Amines • 10.2.1 Nomenclature, Physical and Chemical Properties • 10.2.2 Preparation of Amines • 10.2.3 Reactions of Amines (Other Than alkylation) • 10.2.4 Heterocycles • 10.2.5 Separations of Organic Mixtures • 10.3 Amides • 10.3.1 Amides – Nomenclature, Physical, and Chemical Properties • 10.3.2 Preparation of Amides • 10.3.3 Reactions of Amides • 10.4 Problems
- • 11 Introduction to Spectroscopy
- • 11.1 Introduction • 11.2 First Things First • 11.3 Infrared (IR) Spectroscopy • 11.3.1 Introduction and General Principles • 11.3.2 IR Correlations • 11.4 The Appearance of an IR Spectrum • 11.5 How to Use IR data • 11.6 Nuclear Magnetic Resonance • 11.7 The Scale • 11.8 The Chemical Shift • 11.9 The Integral • 11.10 13C NMR Spectra • 11.11 Spin–Spin Coupling • 11.12 Shoolery’s Rules • 11.13 Putting It All Together • 11.14 Problems
- • 12 Elimination Reactions
- • 12.1 Introduction • 12.2 Possible Mechanisms – Background and Review • 12.3 E1 Mechanism – The Carbocation Route • 12.4 E2 Mechanism – The Concerted Route • 12.4.1 Prototypical E2 Elimination Reactions • 12.5 Regiochemistry and Stereochemistry of Eliminations • 12.5.1 E1 Eliminations • 12.5.2 E2 Eliminations • 12.6 Stereochemical Effects in E2 Eliminations • 12.6.1 Consequences in Cyclic Systems • 12.7 E1 Versus E2 Eliminations • 12.7.1 Leaving Group • 12.7.2 Base • 12.7.3 Substrate Structure • 12.7.4 Solvent • 12.8 Elimination Versus Substitution (E2 vs SN2) • 12.8.1 Nature of Base • 12.8.2 Nature of Substrate • 12.9 The E1cB Mechanism • 12.10 Problems
- • Part II: The Naming of Organic Compounds
- • 13 Introduction
- • 14 Basic Principles
- • 15 Alkenes, Alkynes, and Compounds With Rings
- • 16 More Stereochemistry – The CIP System
- • 17 Functional Groups
- • 18 Aromatic Compounds
- • Appendix: Answers to Problems From Part II
- • Index
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