xvii PART SIX Aromatic Compounds 867 MasteringChemistry 18 Reactions of Benzene and Substituted Benzenes 868 ing.These GENERAL CONNECTION-Measurin 18.1 The Nom CON clature of Monosubstituted Benzenes 870 ECTION: el M iSubstitution Reactions 871 Sulfonation of Benzene875 riede-cratts of Renzene by acvlatio Reduction 880 sn Couplin Reactions to Alkylate Benzen 884 The Nome 882 89( 896 181 hesis of Trisubstituted Benzenes 898 1819 stituted Benzenes Using Arenediazonium Salts HISTORICAL CONNECTION:Dis overy of the First Antibiotic 904 ety 904 18.20 m lon 905 1821 Cancer 18.22 DESIGNING A SYNTHESIS VI:The Synthesis of Cyclic Compounds 909 ESSENTIAL CONCEPTS 910 SUMMARY OF REACTIONS 911 PROBLEMS 913 19 More About Amines.Reactions of Heterocyclic Compounds 924 18 erties of Amines 926 MEDICAL CONNECTION:Atropine 927 19.5 Aromatic Five-Membered-Rin Heterocycles 18 ome H c Amines H ine and a prue fo 19.8 MEoicALcoEcTOtPeohnBnabin,anaaOdicec Organizing ompounds (Group IV)943 ESSENTIAL CONCEPTS 944 SUMMARY OF REACTIONS 945.PROBLEMS 946
for Organic Chemistry MasteringChemistry tutorials guide you through the toughest topics in chemistry with self-paced tutorials that provide individualized coaching. These assignable, in-depth tutorials are designed to coach you with hints and feedback specific to your individual misconceptions. For additional practice on Synthesis and Retrosynthetic Analysis, go to MasteringChemistry where the following tutorials are available: • Synthesis and Retrosynthetic Analysis: Changing the Functional Group • Synthesis and Retrosynthetic Analysis: Disconnections • Synthesis and Retrosynthetic Analysis: Synthesis of Carbonyl Compounds PART SIX Aromatic Compounds 867 18 Reactions of Benzene and Substituted Benzenes 868 GENERAL CONNECTION: Measuring Toxicity 869 18.1 The Nomenclature of Monosubstituted Benzenes 870 GENERAL CONNECTION: The Toxicity of Benzene 871 18.2 The General Mechanism for Electrophilic Aromatic Substitution Reactions 871 18.3 Halogenation of Benzene 872 MEDICAL CONNECTION: Thyroxine 874 18.4 Nitration of Benzene 874 18.5 Sulfonation of Benzene 875 18.6 Friedel–Crafts Acylation of Benzene 876 18.7 Friedel–Crafts Alkylation of Benzene 877 CHEMICAL CONNECTION: Incipient Primary Carbocations 879 BIOLOGICAL CONNECTION: A Biological Friedel-Crafts Alkylation 879 18.8 Alkylation of Benzene by Acylation–Reduction 880 18.9 Using Coupling Reactions to Alkylate Benzene 881 18.10 How Some Substituents on a Benzene Ring Can Be Chemically Changed 882 18.11 The Nomenclature of Disubstituted and Polysubstituted Benzenes 884 18.12 The Effect of Substituents on Reactivity 886 18.13 The Effect of Substituents on Orientation 890 18.14 The Ortho–Para Ratio 894 18.15 Additional Considerations Regarding Substituent Effects 894 18.16 DESIGNING A SYNTHESIS VI: The Synthesis of Monosubstituted and Disubstituted Benzenes 896 18.17 The Synthesis of Trisubstituted Benzenes 898 18.18 Synthesizing Substituted Benzenes Using Arenediazonium Salts 900 18.19 Azobenzenes 903 HISTORICAL CONNECTION: Discovery of the First Antibiotic 904 PHARMACEUTICAL CONNECTION: Drug Safety 904 18.20 The Mechanism for the Formation of a Diazonium Ion 905 MEDICAL CONNECTION: A New Cancer-Fighting Drug 905 NUTRITIONAL CONNECTION: Nitrosamines and Cancer 906 18.21 Nucleophilic Aromatic Substitution 907 18.22 DESIGNING A SYNTHESIS VII: The Synthesis of Cyclic Compounds 909 ESSENTIAL CONCEPTS 910 ■ SUMMARY OF REACTIONS 911 ■ PROBLEMS 913 19 More About Amines • Reactions of Heterocyclic Compounds 924 19.1 More About Nomenclature 925 19.2 More About the Acid–Base Properties of Amines 926 MEDICAL CONNECTION: Atropine 927 19.3 Amines React as Bases and as Nucleophiles 927 19.4 Synthesis of Amines 929 19.5 Aromatic Five-Membered-Ring Heterocycles 929 PROBLEM-SOLVING STRATEGY 931 19.6 Aromatic Six-Membered-Ring Heterocycles 934 19.7 Some Heterocyclic Amines Have Important Roles in Nature 939 PHARMACEUTICAL CONNECTION: Searching for Drugs: An Antihistamine, a Nonsedating Antihistamine, and a Drug for Ulcers 940 MEDICAL CONNECTION: Porphyrin, Bilirubin, and Jaundice 943 19.8 Organizing What We Know About the Reactions of Organic Compounds (Group IV) 943 ESSENTIAL CONCEPTS 944 ■ SUMMARY OF REACTIONS 945 ■ PROBLEMS 946 xvii
PART SEVEN Bioorganic Compounds 949 20 The Organic Chemistry of Carbohydrates 950 951 The Configurations of Aldoses 953 95 of Mo Basic Solutions Oxidation- 20.9 MEDICAL CONNECTION:Me 962 20.12 Formation of Gly osides 967 cing Sugars 969 erance 971 BIOLOGICAL CONNECTION:A Toxic Disaccharide 972 20.16 MEDICAL CONNECTION:WH the Dentist is Right 74 BIOLOGICAL CONNECTION:Controlling FI leas 975 20.17 MEDICAL ing c MEDICAL ECTION:Heparin-A Natu 20.1 es on Cell surtaces 97a 978 cceptable Daily Intake 981 CONCEPTS 98 SUMMARY OF REACTIONS 982 PROBLEMS 983 Amino Acids,Peptides,and Proteins 986 New art adds clarity. 21 21.1 The Nomenclature of Amino Acids 987 eins and Nutrition 991 21.2 NUTRITIONAL CONNECTION:Pro MEDICAL CONNECTION:Amino Acids and Disease2 CONNECTION:A Peptide Antibiotic992 21.5 Softeners:Examples of Cation-Exchange Chromatography 100 on of Racemic Mixtur 1006 aight or Curly?1006 919 The Strategy of Peptide Bond Synthesis:N-Protection and C-Activation 1007 ctptidepehesuc101e 1013 21.13
xviii PART SEVEN Bioorganic Compounds 949 20 The Organic Chemistry of Carbohydrates 950 20.1 Classifying Carbohydrates 951 20.2 The d and l Notation 952 20.3 The Configurations of Aldoses 953 20.4 The Configurations of Ketoses 955 20.5 The Reactions of Monosaccharides in Basic Solutions 956 20.6 Oxidation–Reduction Reactions of Monosaccharides 957 20.7 Lengthening the Chain: The Kiliani–Fischer Synthesis 958 20.8 Shortening the Chain: The Wohl Degradation 959 MEDICAL CONNECTION: Measuring the Blood Glucose Levels in Diabetes 960 20.9 The Stereochemistry of Glucose: The Fischer Proof 960 GENERAL CONNECTION: Glucose/Dextrose 962 20.10 Monosaccharides Form Cyclic Hemiacetals 962 20.11 Glucose is the Most Stable Aldohexose 965 20.12 Formation of Glycosides 967 20.13 The Anomeric Effect 968 20.14 Reducing and Nonreducing Sugars 969 20.15 Disaccharides 969 NUTRITIONAL CONNECTION: Lactose Intolerance 971 MEDICAL CONNECTION: Galactosemia 971 BIOLOGICAL CONNECTION: A Toxic Disaccharide 972 20.16 Polysaccharides 973 MEDICAL CONNECTION: Why the Dentist is Right 974 BIOLOGICAL CONNECTION: Controlling Fleas 975 20.17 Some Naturally Occurring Compounds Derived from Carbohydrates 976 MEDICAL CONNECTION: Resistance to Antibiotics 976 MEDICAL CONNECTION: Heparin–A Natural Anticoagulant 977 HISTORICAL CONNECTION: Vitamin C 978 20.18 Carbohydrates on Cell Surfaces 978 20.19 Artificial Sweeteners 979 NUTRITIONAL CONNECTION: Acceptable Daily Intake 981 ESSENTIAL CONCEPTS 981 ■ SUMMARY OF REACTIONS 982 ■ PROBLEMS 983 21 Amino Acids, Peptides, and Proteins 986 21.1 The Nomenclature of Amino Acids 987 NUTRITIONAL CONNECTION: Proteins and Nutrition 991 21.2 The Configuration of Amino Acids 991 MEDICAL CONNECTION: Amino Acids and Disease 992 PHARMACEUTICAL CONNECTION: A Peptide Antibiotic 992 21.3 Acid–Base Properties of Amino Acids 993 21.4 The Isoelectric Point 995 21.5 Separating Amino Acids 996 GENERAL CONNECTION: Water Softeners: Examples of Cation-Exchange Chromatography 1000 21.6 Synthesis of Amino Acids 1000 21.7 Resolution of Racemic Mixtures of Amino Acids 1002 21.8 Peptide Bonds and Disulfide Bonds 1003 MEDICAL CONNECTION: Diabetes 1006 CHEMICAL CONNECTION: Hair: Straight or Curly? 1006 21.9 Some Interesting Peptides 1006 21.10 The Strategy of Peptide Bond Synthesis: N-Protection and C-Activation 1007 21.11 Automated Peptide Synthesis 1010 21.12 An Introduction to Protein Structure 1013 BIOLOGICAL CONNECTION: Primary Structure and Taxonomic Relationship 1013 21.13 How to Determine the Primary Structure of a Polypeptide or a Protein 1013 PROBLEM-SOLVING STRATEGY 1015 New art adds clarity
xix 21.14 Secondary Structure 1019 CAL to prove on 102 21.15 Tertiary Struct ure 102 2116 Protein 21.17 Protein Denaturation 1025 ESSENTIAL CONCEPTS 1025 PROBLEMS 1026 Catalysis Reactions 1030 221 Catalysis in Organic Reactions 1032 Acid Catalysis 1032 se Ca 103 1037 Metal-lon Catalysis103 Cataons action That Is Reminiscent of Acid-Catalyzed 22.10 zyme- Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed 22.11 An Enzyme-Catalyzed Reaction That Involves Two Sequential SN2 Reactions 1052 22.12 nediol Rearrangement 1056 eminiscent of the Base-Catalyzed 2.13 alyzed-Reac tion That Is Reminiscent of a Retro-Aldol Addition 1057 ESSENTIAL CONCEPTS 1059PR0BL2M5106 Cemyothe Cozymomunds Derived from Vitamins 1063 231 CONNECTION:Niacin De ox Reactions 1066 ncy 1067 1075 The Vitamin Needed for Amino Acid Transformations 1081 NECTION:ASS ssing the Dam Folic Acid:The Vitamin Needed for One-Carbon Transfer ide Ef 10e251092 GCAL CONNECTION: 23.8 NUTRITIONAL CONNECTION:Too Much Broccoli 1095 ESSENTIAL CONCEPTS 1095 PROBLEMS 1096 The Organic Chemistry of the Metabolic Pathways1099 NUTRITIONAL CONNECTION:Diffe in Metabolism 1100 241 ATP is U ed for Phos sphoryl Transfer Reactions 1100 Why ATP is K ose Phosphates?1102 High-Energy" acter of Pr sphoanhydride Bonds 1102 The catabolism of Fats:Stages l and 2 1105 24.6 The Catabolism of Carbohydrates:Stages 1 and 2 1108 PROBLEM-SOLVING STRATEGY 1111
21.14 Secondary Structure 1019 CHEMICAL CONNECTION: Right-Handed and Left-Handed Helices 1020 CHEMICAL CONNECTION: b-Peptides: An Attempt to Improve on Nature 1022 21.15 Tertiary Structure 1022 MEDICAL CONNECTION: Diseases Caused by a Misfolded Protein 1024 21.16 Quaternary Structure 1024 21.17 Protein Denaturation 1025 ESSENTIAL CONCEPTS 1025 ■ PROBLEMS 1026 22 Catalysis in Organic Reactions and in Enzymatic Reactions 1030 22.1 Catalysis in Organic Reactions 1032 22.2 Acid Catalysis 1032 22.3 Base Catalysis 1035 22.4 Nucleophilic Catalysis 1037 22.5 Metal-Ion Catalysis 1038 22.6 Intramolecular Reactions 1040 22.7 Intramolecular Catalysis 1042 22.8 Catalysis in Biological Reactions 1044 22.9 An Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide Hydrolysis 1046 22.10 Another Enzyme-Catalyzed Reaction That Is Reminiscent of Acid-Catalyzed Amide Hydrolysis 1049 22.11 An Enzyme-Catalyzed Reaction That Involves Two Sequential SN2 Reactions 1052 MEDICAL CONNECTION: How Tamiflu Works 1055 22.12 An Enzyme-Catalyzed Reaction That Is Reminiscent of the Base-Catalyzed Enediol Rearrangement 1056 22.13 An Enzyme Catalyzed-Reaction That Is Reminiscent of a Retro-Aldol Addition 1057 ESSENTIAL CONCEPTS 1059 ■ PROBLEMS 1060 23 The Organic Chemistry of the Coenzymes, Compounds Derived from Vitamins 1063 HISTORICAL CONNECTION: Vitamin B1 1065 23.1 Niacin: The Vitamin Needed for Many Redox Reactions 1066 HISTORICAL CONNECTION: Niacin Deficiency 1067 23.2 Riboflavin: Another Vitamin Used in Redox Reactions 1071 23.3 Vitamin B1: The Vitamin Needed for Acyl Group Transfer 1075 GENERAL CONNECTION: Curing a Hangover with Vitamin B1 1078 23.4 Biotin: The Vitamin Needed for Carboxylation of an a-Carbon 1079 23.5 Vitamin B6: The Vitamin Needed for Amino Acid Transformations 1081 MEDICAL CONNECTION: Assessing the Damage After a Heart Attack 1085 23.6 Vitamin B12: The Vitamin Needed for Certain Isomerizations 1086 23.7 Folic Acid: The Vitamin Needed for One-Carbon Transfer 1088 HISTORICAL CONNECTION: The First Antibiotics 1089 MEDICAL CONNECTION: Cancer Drugs and Side Effects 1092 BIOLOGICAL CONNECTION: Competitive Inhibitors 1092 23.8 Vitamin K: The Vitamin Needed for Carboxylation of Glutamate 1093 MEDICAL CONNECTION: Anticoagulants 1095 NUTRITIONAL CONNECTION: Too Much Broccoli 1095 ESSENTIAL CONCEPTS 1095 ■ PROBLEMS 1096 24 The Organic Chemistry of the Metabolic Pathways 1099 NUTRITIONAL CONNECTION: Differences in Metabolism 1100 24.1 ATP is Used for Phosphoryl Transfer Reactions 1100 CHEMICAL CONNECTION: Why Did Nature Choose Phosphates? 1102 24.2 Why ATP is Kinetically Stable in a Cell 1102 24.3 The “High-Energy” Character of Phosphoanhydride Bonds 1102 24.4 The Four Stages of Catabolism 1104 24.5 The Catabolism of Fats: Stages 1 and 2 1105 24.6 The Catabolism of Carbohydrates: Stages 1 and 2 1108 PROBLEM-SOLVING STRATEGY 1111 xix Increased emphasis on the connection between the reactions that occur in the laboratory and those that occur in cells
24.7 24.8 Inborn Error of Metabolism 1114 MEDICAL CONNECTION:Alcaptonuria 1115 m 1119 1120 Amino A 5s112 ESSENTIAL CONCEPTS 1124 PROBLEMS 1125 25The organie chemiatry oipid 25.1 Fatty Acids Are Long-Chain Carboxylic Acids 1128 chapt 25.2 WarerHig-Melecur 25.3 new material. 61130 Soaps and Micelles 1132 nom anes 1134 Terpenes Contain Carbon Atoms in Multiples of Five 1139 25.8 Cholesterol Levels 114 PROBLEM-SOLVING STRATEGY 1144 CHEMICAL CONNECTION:Protein Prenylation 1146 MEDICAL CONNECTION:One Drug-Two Effects 1149 25.11 Steroids 1150 ESSENTIAL CONCEPTS 1151 PROBLEMS 1152 The Chemistry of the Nucleic Acids5 26.1 d Nucleotides 1155 BIOLOGICAL CONNECTION:AMP 115 DNA:Watson,Crick.Franklin,and Wilkins 1158 Nucl Acids Are Com Nucle otide Subunits 1159 Why DNA Does Not v -OH Gr 1163 PHARMACEUTICAL CONNECTION:Natural Products That Modity DNA116 26.7 ses in DNA 1166 26.8 The RNAs Used for Protein Biosynthesis 1167 26.9 TeBioscheesotProteinslsca alled Trans ion 1169 MEDICAL CONNECTION:Antibiotics That Act by y Inhibiting Translation 1172 26.10 03 nism 1174 26.11 Antiviral 1174 26.12 o the Bas 26.13 Genetic Engineering 1177
NUTRITIONAL CONNECTION: Fats Versus Carbohydrates as a Source of Energy 1112 24.7 The Fate of Pyruvate 1112 24.8 The Catabolism of Proteins: Stages 1 and 2 1113 MEDICAL CONNECTION: Phenylketonuria (PKU): An Inborn Error of Metabolism 1114 MEDICAL CONNECTION: Alcaptonuria 1115 24.9 The Citric Acid Cycle: Stage 3 1115 24.10 Oxidative Phosphorylation: Stage 4 1118 NUTRITIONAL CONNECTION: Basal Metabolic Rate 1119 24.11 Anabolism 1119 24.12 Gluconeogenesis 1120 24.13 Regulating Metabolic Pathways 1122 24.14 Amino Acid Biosynthesis 1123 ESSENTIAL CONCEPTS 1124 ■ PROBLEMS 1125 25 The Organic Chemistry of Lipids 1127 25.1 Fatty Acids Are Long-Chain Carboxylic Acids 1128 NUTRITIONAL CONNECTION: Omega Fatty Acids 1129 25.2 Waxes Are High-Molecular-Weight Esters 1130 25.3 Fats and Oils Are Triglycerides 1130 NUTRITIONAL CONNECTION: Olestra: Nonfat with Flavor 1132 BIOLOGICAL CONNECTION: Whales and Echolocation 1132 25.4 Soaps and Micelles 1132 25.5 Phospholipids Are Components of Cell Membranes 1134 BIOLOGICAL CONNECTION: Snake Venom 1136 MEDICAL CONNECTION: Multiple Sclerosis and the Myelin Sheath 1137 25.6 Prostaglandins Regulate Physiological Responses 1137 25.7 Terpenes Contain Carbon Atoms in Multiples of Five 1139 25.8 How Terpenes Are Biosynthesized 1141 MEDICAL CONNECTION: How Statins Lower Cholesterol Levels 1142 PROBLEM-SOLVING STRATEGY 1144 CHEMICAL CONNECTION: Protein Prenylation 1146 25.9 How Nature Synthesizes Cholesterol 1147 25.10 Steroids 1148 MEDICAL CONNECTION: One Drug—Two Effects 1149 25.11 Synthetic Steroids 1150 ESSENTIAL CONCEPTS 1151 ■ PROBLEMS 1152 26 The Chemistry of the Nucleic Acids 1155 26.1 Nucleosides and Nucleotides 1155 HISTORICAL CONNECTION: The Structure of DNA: Watson, Crick, Franklin, and Wilkins 1158 BIOLOGICAL CONNECTION: Cyclic AMP 1159 26.2 Nucleic Acids Are Composed of Nucleotide Subunits 1159 26.3 The Secondary Structure of DNA 1161 26.4 Why DNA Does Not Have A 2′-OH Group 1163 26.5 The Biosynthesis of DNA Is Called Replication 1163 26.6 DNA and Heredity 1164 PHARMACEUTICAL CONNECTION: Natural Products That Modify DNA 1165 26.7 The Biosynthesis of RNA Is Called Transcription 1165 BIOLOGICAL CONNECTION: There Are More Than Four Bases in DNA 1166 26.8 The RNAs Used for Protein Biosynthesis 1167 26.9 The Biosynthesis of Proteins Is Called Translation 1169 MEDICAL CONNECTION: Sickle Cell Anemia 1171 MEDICAL CONNECTION: Antibiotics That Act by Inhibiting Translation 1172 26.10 Why DNA Contains Thymine Instead of Uracil 1173 MEDICAL CONNECTION: Antibiotics Act by a Common Mechanism 1174 26.11 Antiviral Drugs 1174 HISTORICAL CONNECTION: Influenza Pandemics 1175 26.12 How the Base Sequence of DNA Is Determined 1175 26.13 Genetic Engineering 1177 The lipid material previously in the chapter on carboxylic acids and their derivatives has been moved into this new chapter. The discussion of terpenes from the metabolism chapter has also been moved into this chapter, along with some new material. xx
ESSENTIAL CONCEPTS 1178 PROBLEMS 1178 PART Special Topics in Organic Chemistry 1181 EIGHT 2Synthetic Potymers 12 tion 27.3 274 Anionic Polym rization 1192 Polymerization of Dienes 1196 PHARMACEUTICAL CONNECTION:Nanocontainers 1198 An Introduction to Step-Growth Polymers 1199 MEDICAL::Bisphenol A and Phthalates 1202 27.12 NUTRITIONAL CONNECTION:Melamine Poisoning 1205 ecycling Polymers 1206 207 ESSENTIAL CONCEPTS 1208 PROBLEMS 120e 28 Pericyclic Reactions 1212 Electrocyclic Reactions 1218 Cycloaddition Reactions 122 in Biological Systems 1232 1234 NUTRITIONAL CONNECTION:Animals,Birds,Fist 28.7 tion Rules for Pericycl React ESSENTIAL CONCEPTS 1236 PROBLEMS 1236 Appendices A-1 I PK.VALUES A-1 I KINETICS A.3 IIl SUMMARY OF METHODS USED TO SYNTHESIZE A PARTICULAR FUNCTIONAL GROUP A-S IV SUMMARY OF METHODS EMPLOYED TO FORM CARBON-CARBON BONDS A-11 V SPECTROSCOPY TABLES A-12 VI PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS A-18 ANSWERS TO SELECTED PROBLEMS ANS- INDEX 1-1
ENVIRONMENTAL CONNECTION: Resisting Herbicides 1177 PHARMACEUTICAL CONNECTION: Using Genetic Engineering to Treat the Ebola Virus 1177 ESSENTIAL CONCEPTS 1178 ■ PROBLEMS 1178 PART EIGHT Special Topics in Organic Chemistry 1181 27 Synthetic Polymers 1182 27.1 There Are Two Major Classes of Synthetic Polymers 1183 27.2 An Introduction To Chain-Growth Polymers 1184 27.3 Radical Polymerization 1184 INDUSTRIAL CONNECTION: Teflon: An Accidental Discovery 1187 ENVIRONMENTAL CONNECTION: Recycling Symbols 1189 27.4 Cationic Polymerization 1189 27.5 Anionic Polymerization 1192 27.6 Ring-Opening Polymerizations 1193 27.7 Stereochemistry of Polymerization • Ziegler–Natta Catalysts 1195 27.8 Polymerization of Dienes 1196 27.9 Copolymers 1198 PHARMACEUTICAL CONNECTION: Nanocontainers 1198 27.10 An Introduction to Step-Growth Polymers 1199 27.11 Classes of Step-Growth Polymers 1200 MEDICAL CONNECTION: Health Concerns: Bisphenol A and Phthalates 1202 INDUSTRIAL CONNECTION: Designing a Polymer 1203 27.12 Physical Properties of Polymers 1204 NUTRITIONAL CONNECTION: Melamine Poisoning 1205 27.13 Recycling Polymers 1206 27.14 Biodegradable Polymers 1207 ESSENTIAL CONCEPTS 1208 ■ PROBLEMS 1208 28 Pericyclic Reactions 1212 28.1 There Are Three Kinds of Pericyclic Reactions 1213 28.2 Molecular Orbitals and Orbital Symmetry 1215 28.3 Electrocyclic Reactions 1218 28.4 Cycloaddition Reactions 1224 28.5 Sigmatropic Rearrangements 1227 28.6 Pericyclic Reactions in Biological Systems 1232 CHEMICAL CONNECTION: Bioluminescence 1233 NUTRITIONAL CONNECTION: The Sunshine Vitamin 1234 NUTRITIONAL CONNECTION: Animals, Birds, Fish—And Vitamin D 1235 28.7 Summary of the Selection Rules for Pericyclic Reactions 1235 ESSENTIAL CONCEPTS 1236 ■ PROBLEMS 1236 Appendices A-1 I PKA VALUES A-1 II KINETICS A-3 III SUMMARY OF METHODS USED TO SYNTHESIZE A PARTICULAR FUNCTIONAL GROUP A-8 IV SUMMARY OF METHODS EMPLOYED TO FORM CARBON-CARBON BONDS A-11 V SPECTROSCOPY TABLES A-12 VI PHYSICAL PROPERTIES OF ORGANIC COMPOUNDS A-18 ANSWERS TO SELECTED PROBLEMS ANS-1 GLOSSARY G-1 CREDITS C-1 INDEX I-1 xxi