ORGANIC CHEMISTRY: PHYSICAL CHEMISTRY FOR MEDICAL, PHARMACEUTICAL, AND BIOLOGICAL STUDENTS, WITH PRACTICAL EXERCISES
1 Alkanes, Composition, Constitution and Configuration 1 11 On the Nomenclature of Organic Compounds 5 12 Configurations and Shapes of Molecules 7 13 Molecular Dynamics and Conformations 11 14 Cycloalkanes 14 141 Cyclohexane 14 142 Cyclopentane 16 143 Cyclobutane and Cyclopropane 17 15 Polycyclic Hydrocarbons 17 2 Functional Groups 19 3 Electronic Structure of Organic Molecules 23 31 The Covalent Bond 23 32 Molecular Orbitals 26 33 Distribution of Electron Density, and the Shape of Molecules 32 34 Bond Lengths, Bond Energies, and Molecular Vibrations 33 35 Determination of the Molecular Structure by Nuclear Magnetic Resonance Spectroscopy 37 4 Alkenes and Alkynes 43 41 Constitution and Nomenclature 43 42 Configuration of Alkenes 45 43 Electronic Structure and Reactions of Alkenes 48 44 Addition Reactions of Alkenes, and the Concept of Reaction Mechanism 50 45 Additions of Hydrogen Halides 51 46 Oxidations and Polymerizations of Alkenes 56 47 Aromatic Hydrocarbons 57 48 Hydrocarbons in Biology 61 5 Substitutions on Saturated Carbon Atom 63 51 Radical Substitutions 64 511 Alkyl Halides 64 512 Bond Polarity and the Dipole Moment 67 52 Reactions of Nucleophilic Substitutions and Eliminations 69 521 Reaction Mechanisms of Nucleophilic Substitutions 70 522 Alcohols 74 523 Ethers 81 524 Thiols and Sulfides 84 525 Amines 85 6 Nucleophilic Additions 89 61 Aldehydes and Ketones 90 611 Carbon as a Nucleophile 96 612 Condensations with Amines 99 613 Reductions of Aldehydes and Ketones 100 62 Carboxylic Acids 101 7 Stereochemistry, Symmetry and Molecular Chirality 109 8 Derivatives of Carboxylic Acids 117 81 Anhydrides 118 82 Esters, Nucleophilic Substitution on the Unsaturated Carbon Atom 118 83 Acyl-Halides 121 84 Amides 123 9 Electrophilic Substitutions 127 91 Substituent Effects in Electrophilic Aromatic Substitution 130 10 Pericyclic Reactions 137 11 Organic Natural Products 141 111 Amino Acids and Peptides 142 112 Carbohydrates 154 1121 Cyclic Structures of Monosaccharides 159 1122 Disaccharides and Polysaccharides 162 113 Glycosides and Nucleotides 165 114 Lipids 169 1141 Waxes 169 1142 Fats 170 1143 Phospholipids 171 1144 Terpenes and Steroids 173 115 Alkaloids 177 116 Organic and Bioorganic Reactions 178 117 Organic Synthesis 183 12 Organic Supramolecular and Supermolecular Structures 187 121 Molecular Recognition and Catalysis 191