EFFICIENTLY STUDYING ORGANIC CHEMISTRY : exam training for chemists, biochemists, pharmacists... , life and health scientists

Complete yet concise learning resource for organic chemistry exam training. Based on the author’s extensive teaching experience, this unique textbook comprises the essentials of organic chemistry in 86 chapters as concise, self-contained units of study. Each chapter, visually presented as one or two double pages, includes questions to allow for immediate and effective self-examination. Answers are summarized in the appendix. Topics covered within the book include: Basic concepts (atomic and molecular orbitals, covalent bonding, hybridization, resonance, aromaticity) Molecular structure (atom connectivity, skeletal isomerism, conformation, configuration, chirality) The classes of organic compounds including natural products, polymers, and biopolymers Types, mechanisms, selectivity, and specificity of organic reactions Molecular structure elucidation (mass spectrometry, UV and visible light absorption, IR and NMR spectroscopy) Planning organic syntheses The perfect fit for bachelor and master students alike, this book is an all-in-one resource for efficiently studying and passing organic chemistry exams. Cover Half Title Efficiently Studying Organic Chemistry: Exam Training for Chemists, Biochemists, Pharmacists, Life and Health Scientists Copyright Contents Organic Chemistry 1. Atomic Orbitals, Electronic Configurations 1.1 Atomic Orbitals 1.2 s and p Orbitals 1.3 Electron Spin and PAULI Principle 1.4 Electronic Configuration of Light Atoms 2. Covalent Bonding 2.1 Kinds of Chemical Bond 2.2 Covalent Bonding by Overlapping of Atomic Orbitals 2.3 Overlapping of p Orbitals 3. Hybridization of Atomic Orbitals 3.1 Geometry of the Methane Molecule 3.2 Hybridization of Atomic Orbitals 3.3 Carbon-Hydrogen Bonding in Methane 4. Covalent Carbon-Carbon Bonding 4.1 Ethane, CC Single Bond 4.2 Ethene, CC Double Bond 4.3 Ethyne, CC Triple Bond 5. Alkanes 5.1 Homologous Series of Alkanes 5.2 Natural Sources and Preparation 5.2.1 Distillation of Petroleum 5.2.2 Catalytic Hydrogenation of Alkenes 5.2.3 WURTZ Synthesis Involving Alkylsodium 5.2.4 KOLBE Electrolysis of Carboxylates (Anodic Oxidation) 5.3 Alkanes as an Energy Source 6. Skeletal Structure, Structural Isomerism 6.1 Two and More Structures for One Molecular Formula 6.2 Skeletal Isomerism 7. Basic Rules of Nomenclature 7.1 IUPAC Rules 7.2 Branched Alkyl Groups 8. Drawing Molecular Structures 8.1 Structural Formulas 8.2 Skeletal Formulas 8.3 LEWIS Formulas 8.4 Projections 8.4.1 FISCHER Projection 8.4.2 NEWMAN Projection 9. Conformation 9.1 Conformation, Conformers 9.2 Energy Contents and Nomenclature of Conformers 10. Reactive Intermediates 10.1 Radicals 10.2 Carbenium Ions and Carbanions 10.3 Carbenes 11. Basic Types of Organic Reactions 11.1 Addition 11.2 Elimination 11.3 Oxidation 11.4 Reduction 11.5 Substitution 11.6 Rearrangement 12. Energy Turnover of Chemical Reactions 12.1 Heat of Reaction, Activation Energy 12.2 Catalysis 12.3 Kinetic and Thermodynamic Control 13. Radical Substitution 13.1 Photohalogenation of Alkanes 13.2 Relative Stability of Alkyl Radicals 13.3 Regioselectivity of Radical Substitution 13.4 Radical Sulfochlorination and Nitration 14. Alkenes, Skeletal and Configurational Isomers 14.1 Nomenclature and Structural Isomerism 14.2 Relative Configuration 15. Synthesis of Alkenes 15.1 β-Elimination 15.1.1 Dehydrohalogenation of Haloalkanes 15.1.2 Dehydration of Alcohols 15.1.3 Reductive Dehalogenation of 1,2-Dihaloalkanes 15.2 Alternative Syntheses 15.2.1 Dehydrogenation of Alkanes 15.2.2 Partial Hydrogenation of Alkynes 15.2.3 Reductive Coupling of Carbonyl Compounds 15.2.4 Carbonyl Alkenylations 15.3 Transformation of Alkenes 15.3.1 WOHL-ZIEGLER Bromination 15.3.2 HECK Reaction 15.3.3 Ene Reaction 15.3.4 Alkene Metathesis 16. Additions to Alkenes 16.1 Addition of Hydrogen (Catalytic Hydrogenation) 16.2 Addition of Bromine (Bromination) 16.3 Electrophilic Addition of Hydrogen Halide (Hydrohalogenation) 16.4 Electrophilic Addition of Water (Hydration) 16.5 Halohydrin Formation 16.6 Hydroboration 16.7 Dihydroxylations 16.8 1,3-Dipolar Cycloaddition of Ozone (Ozonolysis) 17. Dienes 17.1 Cumulation and Conjugation of Double Bonds 17.2 Molecular Structure 17.2.1 Conformation of 1,3-Butadiene 17.2.2 Bond Lengths and Resonance Formulas of 1,3-Butadiene 17.2.3 Molecular Shape of Allene 17.3 Preparation 17.3.1 Catalytic Dehydrogenation of Alkanes to 1,3-Dienes 17.3.2 Dehydration of Diols to 1,3-Dienes 17.3.3 Catalytic Dimerization of Ethyne to 1,3-Butadiene 17.3.4 1,2-Dienes by Elimination 18. Additions and Cycloadditions with 1,3-Dienes 18.1 1,2- and 1,4-Addition 18.2 Cycloadditions 18.2.1 [4+2]-Cycloaddition (DIELS-ALDER Reaction) 18.2.2 [4+1]-Cycloaddition 19. Alkynes 19.1 Homologous Series, Structural Isomerism, Nomenclature 19.2 Preparation 19.2.1 Partial Oxidation of Methane to Ethyne 19.2.2 Carbide Process 19.2.3 Double Dehydrohalogenation of 1,1- or 1,2-Dihaloalkanes 19.2.4 Alkylation of Terminal Alkynes 19.3 Typical Reactions 19.3.1 Hydrogenation and Reduction 19.3.2 Hydroboration 19.3.3 Electrophilic Addition of Halogens 19.3.4 Electrophilic Addition of HX 19.3.5 CH Acidity of Terminal Alkynes, Alkynylides 19.3.6 Oxidative Coupling of Terminal Alkynes 19.3.7 Cyclotri- and Cyclotetramerization 20. Cycloalkanes 20.1 Nomenclature 20.2 Conformation 20.2.1 Cyclopropane 20.2.2 Cyclobutane 20.2.3 Cyclopentane 20.2.4 Cyclohexane 20.3 Configurational Isomerism 20.3.1 cis- and trans-Disubstituted Cycloalkanes 20.3.2 cis- and trans-Decalin 20.3.3 Cycloalkenes 21. Basic Syntheses of Cycloalkanes and Cycloalkenes 21.1 Cyclopropane 21.2 Cyclobutane 21.3 Cyclopentene, Cyclopentane 21.4 Cyclohexane, Cyclohexene 21.5 Cycloheptadiene, Cycloheptane 21.6 Larger Rings 22. Reactions of Cycloalkanes and Cycloalkenes 22.1 Reactions Driven by the Strain of Small Rings 22.2 Alkane-like Reactions 22.3 Alkene-like Reactions 22.3.1 Addition of Bromine 22.3.2 Catalytic Hydrogenation 22.3.3 Dihydroxylations 23. Benzene, Aromaticity, Aromatic Compounds 23.1 Structure of Benzene 23.1.1 Molecular Shape 23.1.2 Heat of Hydrogenation 23.1.3 Resonance Energy and Stabilization, Canonical Formulas 23.2 Molecular Orbital Model of Benzene 23.3 Criteria of Aromaticity 24. Benzenoid Aromatic Compounds 24.1 Monosubstituted Benzenes 24.2 Multiply Substituted Benzenes 24.3 Preparation of Benzenoid Hydrocarbons 24.3.1 Fossil Sources 24.3.2 Cyclotrimerization of Alkynes 25. Electrophilic Substitution of Benzene 25.1 Substituted Benzenes by Electrophilic Substitution: Mechanism 25.2 Electrophilic Halogenation 25.3 Electrophilic Alkylation (FRIEDEL-CRAFTS Alkylation) 25.4 Electrophilic Acylation (FRIEDEL-CRAFTS Acylation) 25.5 Electrophilic Nitration 25.6 Electrophilic Sulfonation 26. Electrophilic Second Substitution of Benzenes 26.1 Resonance Effects of Substituents at the Benzene Ring 26.2 Regioselectivity of Electrophilic Second Substitution of Benzenes 27. Other Reactions of Benzenoid Aromatics 27.1 Nucleophilic Substitution at the Benzenoid Ring 27.2 Radical Substitution at the Side Chain 27.3 Hydrogenation, Reduction, Oxidation 28. Polycyclic Benzenoid Aromatic Compounds 28.1 Fusion of Benzenoid Rings 28.2 Preparation of Aromatic Polycycles 28.3 Electrophilic Substitution of Naphthalene 28.4 Oxidation and Reduction of Naphthalene 28.5 Reactions of Anthracene and Phenanthrene 28.6 Enzymatic Epoxidation of Benzo[a]pyrene 29. Non-benzenoid Aromatic Compounds 29.1 Non-benzenoid Aromatic Ions 29.1.1 Cyclopropenium Cation 29.1.2 Cyclopentadienide Anion 29.1.3 Cycloheptatrienium Cation 29.2 [n]Annulenes 30. Alkyl Halides 30.1 Classification, Nomenclature 30.2 Preparation 30.2.1 Radical Substitution of Alkyl Groups 30.2.2 Addition of Hydrogen Halides and Halogens to Alkenes 30.2.3 Substitution of Hydroxide in Alcohols by Halide 30.2.4 Fluorination with Antimony Trifluoride 30.2.5 Nucleophilic Iodination of Alkyl Halides (FINKELSTEIN Reaction) 30.3 Electronegativity and the Inductive Effect 30.4 Typical Reactions 30.4.1 Nucleophilic Substitution of Halide in Haloalkanes 30.4.2 Dehydrohalogenation (β-Elimination) 30.4.3 Metalation 31. Mechanisms of Nucleophilic Substitution 31.1 Bimolecular Nucleophilic Substitution (Second-Order) 31.2 Monomolecular Nucleophilic Substitution (First-Order) 32. Organometal Compounds 32.1 General Survey 32.2 Preparation 32.2.1 Metalation of Alkyl and Aryl Halides 32.2.2 Transmetalation 32.2.3 Halogen-Metal Exchange 32.2.4 Hydrogen-Metal Exchange 32.3 Preparative Significance 33. Alcohols 33.1 Nomenclature, Classification 33.2 Structure and Physical Properties 33.3 Preparation 33.3.1 Industrial Syntheses of Methanol and Ethanol 33.3.2 Alcoholic Fermentation (Beer, Wine, Distillates) 33.3.3 Hydration of Alkenes 33.3.4 Hydroboration of Alkenes and Oxidation of Trialkylboranes 33.3.5 Reduction of Carbonyl Compounds by Complex Metal Hydrides 33.3.6 Nucleophilic Substitution of Alkyl Halides 33.3.7 Addition of Alkylmagnesium Halides to Carbonyl Compounds 34. Diols, Triols 34.1 Preparation 34.1.1 Dihydroxylation of Alkenes 34.1.2 Hydrolysis of Halohydrins 34.1.3 Bimolecular Reduction of Carbonyl Compounds 34.2 Oxidative Cleavage of Glycols 35. Reactions of Alcohols 35.1 Basicity and Acidity 35.2 Oxidation 35.3 Nucleophilic Substitution 35.4 Esterification 36. Dehydration of Alcohols 36.1 Dehydration of Alcohols to Alkenes 36.2 Dehydration of Fully Alkylated 1,2-Diols to Ketones 37. Ethers 37.1 Nomenclature 37.2 Structure and Physical Properties 37.3 Preparation 37.3.1 Bimolecular Dehydration of Alcohols 37.3.2 Alkoxylation of Alkyl Halides (WILLIAMSON Synthesis) 37.4 Typical Reactions 37.4.1 Formation of Oxonium Salts 37.4.2 Autoxidation (Insertion of Oxygen) 37.4.3 Cleavage of Ethers 38. Amines 38.1 Nomenclature, Classification 38.2 Molecular Shape 38.3 Preparation 38.3.1 Alkylation of Ammonia 38.3.2 Primary Amines by Alkylation of Potassium Phthalimide 38.3.3 Primary Amines by Reduction of Nitriles and Nitro Compounds 39. Reactions of Amines 39.1 Basicity of Alkyl- and Arylamines 39.2 Diazotization of Primary Amines 39.3 N-Nitrosation of Secondary Amines 39.4 Exhaustive Alkylation of Amines 39.5 HOFMANN Elimination of Tetraalkylammonium Hydroxides 39.6 Imines from Primary Amines and Carbonyl Compounds 39.7 Enamines from Secondary Amines and Carbonyl Compounds 39.8 Reductive Amination of Carbonyl Compounds to Amines 40. Diazo and Azo Compounds 40.1 Arenediazonium Salts and Azo Dyes 40.2 Azoalkanes 40.3 Diazoalkanes 41. Carboxylic Acids 41.1 Survey, Nomenclature 41.2 Carboxy Group: Bonding and Resonance Formulas 41.3 Carboxylic Acid Dimers 41.4 Preparation 41.4.1 Carbonylation 41.4.2 Carboxylation 41.4.3 Oxidation of Methyl, Hydroxymethyl, and Aldehyde Groups 41.4.4 Hydrolysis of Carboxylic Acid Derivatives 41.5 Acidity 42. Carboxylic Acid Derivatives 42.1 Carboxylic Acid Esters 42.2 Carboxylic Acid Halides (Acyl Halides) 42.3 Carboxylic Acid Anhydrides 42.4 Carboxylic Acid Amides, Cyclic Imides 42.5 Hydrazides, Hydroxamic Acids, Azides 42.6 Change of the Carboxy Function 42.6.1 Reduction to Primary Alcohols and Aldehydes 42.6.2 Reductive Coupling of Esters (Acyloin Reaction) 42.6.3 Decarboxylation 42.6.4 Dehydration of Carboxamides to Nitriles and Isonitriles 43. Substituted Carboxylic Acids 43.1 Nomenclature 43.2 Halo Acids 43.2.1 Preparation 43.2.2 Reactions 43.3 Hydroxy Acids 43.3.1 Preparation 43.3.2 Reactions 44. Absolute Configuration 44.1 Stereogenic Center, Enantiomers, Chirality 44.2 Optical Activity and Specific Rotation 44.3 Specification of the Absolute Configuration 44.3.1 CAHN-INGOLD-PRELOG Convention [(R)- and (S)-Descriptors] 44.3.2 FISCHER Convention (D- and L-Descriptors) 44.3.3 Correlation of D,L and R,S Descriptors 44.3.4 Racemates and Their Resolution 44.4 Stereospecificity of the Bimolecular Nucleophilic Substitution 45. Enantiomers without Carbon as Stereogenic Center 45.1 Heteroatoms as Stereogenic Centers 45.2 Axial Chirality 45.3 Planar Chirality and Helicity 46. Diastereomers 46.1 Compounds with Two Different Stereogenic Centers 46.2 Compounds with Two Equally Substituted Stereogenic Centers 47. Aldehydes 47.1 Survey, Nomenclature 47.2 Preparation 47.2.1 Oxidation of Methyl and Hydroxymethyl Groups 47.2.2 Hydrolysis of 1,1-Dihaloalkanes 47.2.3 Reduction of Carboxylic Acid Derivatives 47.2.4 Formylation of Arenes 47.3 Molecular Shape, Resonance Formulas, Reactivity 47.4 Reactions Specific for Aldehydes 47.4.1 Oxidation to Carboxylic Acids, Identification Reactions 47.4.2 CANNIZZARO Disproportionation of Aromatic Aldehydes 47.4.3 Addition of Hydrogensulfite 48. Ketones 48.1 Survey, Nomenclature 48.2 Preparation 48.2.1 Oxidation of Secondary Alcohols 48.2.2 Catalytic Oxidation of Alkenes by Air (WACKER Process) 48.2.3 Oxidation of Activated Methylene Groups (RILEY Oxidation) 48.2.4 Acylation of Arenes to Phenones (FRIEDEL-CRAFTS Acylation) 49. Carbonyl Reactions 49.1 Reactions with Oxygen and Sufur Nucleophiles 49.1.1 Hydration (Water as Nucleophile) 49.1.2 Formation of Acetals and Ketals (Alcohols as Nucleophiles) 49.1.3 Formation of Thioacetals (Mercaptals) 49.2 Reactions with Nitrogen Nucleophiles 49.3 Reactions with Carbon Nucleophiles 49.3.1 Alkynylation 49.3.2 Cyanohydrin and Benzoin Reaction 49.3.3 Addition of GRIGNARD Compounds 49.3.4 WITTIG Alkenylation (Carbonyl Alkenylation) 49.4 Reductions 50. CH Acidity of Carbonyl Compounds 50.1 CH Acidity of Carboxylic Acid Esters 50.1.1 CLAISEN Condensation 50.1.2 DIECKMANN Cyclocondensation 50.2 CH Acidity of Aldehydes and Ketones 50.2.1 Aldol Reaction 50.2.2 CLAISEN Condensation 50.2.3 MANNICH Reaction 51. 1,3-Dicarbonyl Compounds 51.1 CH Acidity 51.2 Typical Reactions 51.2.1 Alkylation and Cycloalkylation 51.2.2 Carbonyl Alkenylation (KNOEVENAGEL Alkenylation) 51.2.3 Nucleophilic Addition to CC Double Bonds (MICHAEL Addition) 51.2.4 Oxo-Enol Tautomerism 51.2.5 Cyclizations 52. Phenols 52.1 Nomenclature 52.2 Resonance Formulas, Acidity Relative to Alcohols 52.3 Preparation 52.3.1 HOCK Process (Synthesis of Phenol and Acetone) 52.3.2 Hydrolysis of Substituted Chlorobenzenes 52.3.3 Catalytic Oxidation of Methylarenes 52.3.4 Melting of Arenesulfonates with Alkali Hydroxides 52.3.5 Hydrolysis of Arenediazonium Salts 52.4 Typical Reactions 52.4.1 Conversion into Aryl Ethers (WILLIAMSON Synthesis) 52.4.2 Esterification and FRIES Rearrangement 52.4.3 Electrophilic Substitution 52.4.4 Oxidation 53. Quinones 53.1 Survey and Nomenclature 53.2 Preparation 53.2.1 Oxidation of Phenols and Primary Arenamines 53.2.2 Oxidation of Polycyclic Aromatics 53.2.3 FRIEDEL-CRAFTS Acylation of Arenes with Phthalic Anhydride 53.3 Reactions 53.3.1 Reduction-Oxidation Quinone-Hydroquinone Equilibrium 53.3.2 Autoxidation of Anthrahydroquinone 53.3.3 Additions 53.3.4 Electrophilic Substitutions of Benzenoid Rings 53.3.5 Carbonyl Reactions 54. Organosulfur Compounds 54.1 Sulfur in Organic Compounds 54.2 Organosulfur Compounds with Bivalent Sulfur 54.2.1 Thiols, Thiophenols, Disulfides 54.2.2 Thioethers 54.2.3 Sulfenic Acid Derivatives 54.5.4 Thioaldehydes, Thioketones 54.5.5 Thiolic Acids, Thionic Acids, Dithiocarboxylic Acids 54.3 Compounds with Tetra- and Hexavalent Sulfur 54.3.1 Sulfoxides and Sulfones 54.3.2 Sulfinic and Sulfonic Acids 54.3.3 Sulfonic Acid Derivatives 55. Carbonic Acid Derivatives 55.1 Survey of Derivatives 55.2 Carbonic Acid Chlorides 55.2.1 Phosgene 55.2.2 Carbonic Acid Ester Chlorides 55.3 Carbonic Acid Esters 55.3.1 Dialkyl Carbonates, Dialkyl Dicarbonates 55.3.2 Carbamic Acid Esters (Urethanes) 55.4 Urea, Thiourea, Guanidine 55.4.1 Urea 55.4.2 Guanidine and Thiourea 55.5 Derivatives of Dithio- and Trithiocarbonic Acid 56. Heterocumulenes 56.1 Analogues of Carbon Dioxide 56.2 Carbon Disulfide 56.3 Isocyanates, Isothiocyanates 56.4 Carbodiimides 57. Rearrangements 57.1 Anionotropic 1,2-Shifts 57.1.1 General Mechanisms (Sextet Rearrangements) 57.1.2 1,2-Shifts from Carbon to Carbon 57.1.3 1,2-Shifts from Carbon to Oxygen 57.1.4 1,2-Shifts from Carbon to Nitrogen 57.2 Cationotropic 1,2-Shifts 57.2.1 FAVORSKII Rearrangement (from Carbon to Carbon) 57.2.2 STEVENS Rearrangement (from Nitrogen to Carbon) 57.2.3 WITTIG Rearrangement (from Oxygen to Carbon) 57.3 Rearrangements at Benzenoid Rings 57.4 Sigmatropic Rearrangements 58. Polymers, Polymerization 58.1 Monomers, Oligomers, Polymers 58.2 Vinyl and Diene Polymers 58.3 Polyethers 58.4 Polyesters 58.5 Polyamides 58.6 Polyurethanes, Polyureas 59. Syntheses with Organosilicon Compounds 59.1 Comparison of Organosilicon and Organic Compounds 59.2 Halosilanes 59.3 Preparative Significance of Trimethylsilyl Compounds 59.3.1 Trimethylsilylation 59.3.2 Syntheses with Silyl Enol Ethers 59.4 Silicones 60. Heteroalicycles 60.1 Nomenclature 60.2 Preparation 60.2.1 Intramolecular Cyclizations 60.2.2 Cycloadditions 60.2.3 Catalytic Hydrogenation of Aromatic Heterocycles 60.3 Reactions 60.3.1 Heteroatom as Nucleophile 60.3.2 Ring Opening 60.3.3 Ring Expansion 61. Five-Membered Aromatic Heterocycles 61.1 Survey and Nomenclature 61.2 π-Excessive Aromatic Heterocycles 61.3 Typical Syntheses 61.3.1 Furan, Pyrrole, Thiophene 61.3.2 Azoles 61.4 Typical Reactions 61.4.1 Basicity and Acidity of Pyrrole 61.4.2 Electrophilic Substitutions 61.4.3 1,3-Diene Reactions 61.4.4 Nucleophilic Substitutions 61.4.5 Ring Opening 62. Six-Membered Aromatic Heterocycles 62.1 Survey and Nomenclature 62.2 π-Deficient Aromatic Heterocycles 62.3 Typical Syntheses 62.3.1 Pyridines 62.3.2 Pyrimidines 62.3.3 Pyrylium Salts 62.4 Typical Reactions 62.4.1 Reactions at the Imino Nitrogen 62.4.2 Nucleophilic Substitutions 62.4.3 Electrophilic Substitutions 62.4.4 CH Acidity of Methyl Groups 63. Benzo-Fused Five-Membered Heteroaromatics 63.1 Survey and Nomenclature 63.2 Typical Syntheses 63.2.1 Benzo[b]furan, Benzo[b]thiophene 63.2.2 Benzo[b]pyrrole (Indole) 63.2.3 Benzo-1,3-azoles 63.2.4 Carbazole 63.3 Typical Reactions 63.3.1 Electrophilic Substitutions 63.3.2 Cycloadditions 63.3.3 Reactions of 2- and 3-Hydroxy Derivatives 64. Benzo-Fused Six-Membered Heteroaromatics 64.1 Survey and Nomenclature 64.2 Typical Syntheses 64.2.1 Quinolines 64.2.2 Isoquinolines 64.2.3 Benzopyrylium Salts 64.3 Typical Reactions 64.3.1 Basicity and Reactions at the Imino Nitrogen 64.3.2 Catalytic Hydrogenation and Oxidative Ring Opening 64.3.3 Nucleophilic Additions 64.3.4 Nucleophilic Substitutions 64.3.5 Electrophilic Substitutions 64.3.6 CH Acidity of Methyl Groups 65. Fused Aromatic Heterocycles 65.1 Heterobicycles with Nitrogen as Bridgehead 65.2 Purines 65.2.1 Survey 65.2.2 Syntheses of Purines 65.2.3 Oxidative Cleavage of Purines (Uric Acid) 65.3 Pteridines 65.3.1 Survey 65.3.2 Syntheses of Pteridines 66. Absorption of Light, Color, Dyes 66.1 Absorption of Light, Color 66.2 Dyes and Pigments 66.3 Basic Types of Dyes 66.3.1 Structural Properties of Dyes: Azo Dyes 66.3.2 Polymethine Dyes 66.3.3 Triarylmethine Dyes 66.3.4 Carbonyl Dyes 67. Porphyrinoids 67.1 Porphyrins and Phthalocyanines as Polyaza[18]annulenes 67.2 Porphyrinoids in Blood and Chloroplasts 67.2.1 Heme 67.2.2 Chlorophyll 68. Amino Acids 68.1 General Survey 68.2 Preparation 68.3 Identification 69. Peptides, Proteins 69.1 Amino Acid Sequence 69.2 Biological Function 69.3 Structure of Proteins 69.4 Peptide Synthesis 69.4.1 Protective Groups 69.4.2 Carboxy Activation 69.4.3 Peptide Coupling 70. Alkaloids 70.1 Origin, Significance, Nomenclature 70.2 Biologically Active Alkaloids 71. Carbohydrates: Aldoses and Ketoses 71.1 Aldoses 71.2 Ketoses 71.3 Cyclohemiacetals, Cyclohemiketals: Pyranoses, Furanoses 71.4 Mutarotation 71.5 Typical Reactions 71.5.1 Glycosides, Glycosidation 71.5.2 O-Alkylation, O-Acylation 71.5.3 Reduction and Oxidation 72. Carbohydrates: Oligo- and Polysaccharides 72.1 Oligosaccharides 72.2 Polysaccharides 73. Nucleic Acids: DNA and RNA 73.1 Nucleotides, Nucleosides, Nucleobases 73.2 Base Pairing and Double Helix of DNA 74. Lipids 74.1 Classification 74.2 Fatty Acids, Fats, Soaps 74.2.1 Saturated and Unsaturated Fatty Acids 74.2.2 Waxes, Soaps, Biofuel 75. Polyketides 75.1 Polyketide Pathway 75.2 Selected Polyketides 76. Terpenes 76.1 Survey, Isoprene Rule 76.2 Occurrence, Significance 76.3 Selected Terpenes (Flavors, Fragrances, Active Substances) 76.3.1 Hemi- and Monoterpenes 76.3.2 Sesquiterpenes 76.3.3 Diterpenes 76.3.4 Triterpenes 76.3.5 Tetraterpenes (Carotenoids) 76.3.6 Polyterpenes 77. Steroids 77.1 Survey, Fusion of the Rings 77.2 Cholesterol 77.3 Bile Acids 77.4 Steroid Hormones 78. Selectivity and Specificity of Organic Reactions 78.1 Chemoselectivity 78.2 Regioselectivity 78.3 Stereoselectivity 78.4 Stereospecificity 79. Prochirality, Enantioselectivity 79.1 Prochirality of Tetrahedral Carbon Atoms 79.2 Prochirality of Trigonal Carbon Atoms 79.3 Enantioselectivity 80. Planning Organic Syntheses 80.1 Retrosynthetic Disconnections 80.2 Retrons and Synthons 80.3 Designing Selected Syntheses 80.3.1 2-Ethyl-2-hexenal 80.3.2 Ethyl 2,4-Dioxoheptanoate 80.3.3 2-(4-Isobutylphenyl)propanoic Acid 80.3.4 Δ9-Tetrahydrocannabinol 81. Aspects of Molecular Structure 81.1 Molecular Formula and Double Bond Equivalents 81.2 Skeletal Structure: Atom Connectivities 81.3 Conformation 81.4 Relative Configuration 81.5 Absolute Configuration 82. Mass Spectrometry 82.1 Mass Spectrum 82.2 Base Ion, Molecular Ion 82.3 Fragment Ions and Atom Connectivities 83. Infrared Spectroscopy 83.1 IR Spectrum 83.2 Molecular Vibrations 83.3 Identification of Functional Groups and Structural Units 84. Nuclear Magnetic Resonance: Proton NMR 84.1 Nuclear Magnetic Resonance 84.2 Chemical Shift 84.3 NMR Spectrum and Integration 84.4 Signal Multiplets and Coupling Constants 84.4.1 Signal Multiplets 84.4.2 Coupling Constants and Relative Configuration 85. Nuclear Magnetic Resonance: Carbon-13 NMR 85.1 Carbon-13 as NMR Probe 85.2 Carbon-13 Chemical Shifts 85.3 Carbon-Proton Coupling and Detection of CH Multiplets 86. Nuclear Magnetic Resonance: Two-Dimensional NMR 248 86.1 Homonuclear Shift Correlation 86.1.1 Proton-Proton Shift Correlation (HH COSY) 86.1.2 Carbon-Carbon Shift Correlation 86.2 Heteronuclear Shift Correlation (Carbon-Proton Correlation) Working on Questions Subject Index Periodic Table of the Elements Selected Reference Sources Cover back