Efficiently Studying Organic Chemistry

Eberhard Breitmaier received his PhD in 1966 at the University of Tübingen, Germany. After a postdoctoral fellowship followed by an appointment as assistant professor for organic chemistry at the University of Houston, Texas, USA, from 1967 to 1968, he gained his lecturing qualification (habilitation) at the University of Tübingen in 1971. He was professor for organic chemistry and instrumental analysis at the University of Bonn, Germany, from 1975 to 2004. His research focused on 3-alkoxyacroleins as reagents for organic synthesis, porphyrinoid annulenes, and natural products. He has authored many scientific publications and several textbooks on organic chemistry, NMR spectroscopy, and natural products.

• Contents 1Preface 6Organic Chemistry 71 Atomic Orbitals, Electronic Configurations 82 Covalent Bonding 103 Hybridization of Atomic Orbitals 124 Covalent Carbon-Carbon Bonding 145 Alkanes 166 Skeletal Structure, Structural Isomerism 187 Basic Rules of Nomenclature 208 Drawing Molecular Structures 229 Conformation 2410 Reactive Intermediates 2611 Basic Types of Organic Reactions 2812 Energy Turnover of Chemical Reactions 3013 Radical Substitution 3214 Alkenes, Skeletal and Configurational Isomers 3415 Synthesis of Alkenes 3616 Additions to Alkenes 4017 Dienes 4418 Additions and Cycloadditions with 1,3-Dienes 4619 Alkynes 4820 Cycloalkanes 5221 Basic Syntheses of Cycloalkanes and Cycloalkenes 5622 Reactions of Cycloalkanes and Cycloalkenes 5823 Benzene, Aromaticity, Aromatic Compounds 6024 Benzenoid Aromatic Compounds 6225 Electrophilic Substitution of Benzene 6426 Electrophilic Second Substitution of Benzenes 6627 Other Reactions of Benzenoid Aromatics 6828 Polycyclic Benzenoid Aromatic Compounds 7029 Non-benzenoid Aromatic Compounds 7430 Alkyl Halides 7631 Mechanisms of Nucleophilic Substitution 8032 Organometal Compounds 8233 Alcohols 8434 Diols, Triols 8835 Reactions of Alcohols 9036 Dehydration of Alcohols 9237 Ethers 9438 Amines 9639 Reactions of Amines 9840 Diazo and Azo Compounds 10241 Carboxylic Acids 10642 Carboxylic Acid Derivatives 11043 Substituted Carboxylic Acids 11444 Absolute Configuration 11845 Enantiomers without Carbon as Stereogenic Center 12246 Diastereomers 12447 Aldehydes 12648 Ketones 13049 Carbonyl Reactions 13250 CH Acidity of Carbonyl Compounds 13651 1,3-Dicarbonyl Compounds 13852 Phenols 14253 Quinones 14654 Organosulfur Compounds 15055 Carbonic Acid Derivatives 15456 Heterocumulenes 15857 Rearrangements 16058 Polymers, Polymerization 16459 Syntheses with Organosilicon Compounds 16860 Heteroalicycles 17061 Five-Membered Aromatic Heterocycles 17462 Six-Membered Aromatic Heterocycles 17863 Benzo-Fused Five-Membered Heteroaromatics 18264 Benzo-Fused Six-Membered Heteroaromatics 18665 Fused Aromatic Heterocycles 19066 Absorption of Light, Color, Dyes 19467 Porphyrinoids 19868 Amino Acids 20069 Peptides, Proteins 20270 Alkaloids 20671 Carbohydrates: Aldoses and Ketoses 20872 Carbohydrates: Oligo- and Polysaccharides 21273 Nucleic Acids: DNA and RNA 21474 Lipids 21675 Polyketides 21876 Terpenes 22077 Steroids 22478 Selectivity and Specificity of Organic Reactions 22679 Prochirality, Enantioselectivity 23080 Planning Organic Syntheses 23281 Aspects of Molecular Structure 23682 Mass Spectrometry 23883 Infrared Spectroscopy 24084 Nuclear Magnetic Resonance: Proton NMR 24285 Nuclear Magnetic Resonance: Carbon-13 NMR 24686 Nuclear Magnetic Resonance: Two-Dimensional NMR 248Working on Questions 250Subject Index 295Periodic Table of the Elements 314Selected Reference Sources 316