CH 209 Syllabus
References to Organic Chemistry by McMurry, Brooks/Cole, 3rd Edition.
Chapter 22: Carbonyl Alpha-Substitution Reactions
22.1 Keto-Enol Tautomerism p 845
22.2 Reactivity of Enols: The Mechanism of Alpha Substitution Reactions
p 848
22.3 Alpha Halogenation of Ketones and Aldehydes p 848
22.4 Alpha Bromination of Carboxylic Acids: The Hell Volhard-Zelinskii
Reaction p 852
22.5 Acidity of Alpha-Hydrogen Atoms: Enolate Ion Formation p 853
22.6 Reactivity of Enolate Ions p 857
22.7 Halogenation of Enolate Ions: The Haloform Reaction p 858
22.8 Selenenylation of Enolate Ions: Enone Synthesis p 859
22.9 Alklation of Enolate Ions 862
Chapter 23: Carbonyl Condensation Reactions
23.1 General Mechanism of Carbonyl Condensation Reactions p 880
23.2 Condensations of Aldehydes and Ketones: The Aldol Reaction p 882
23.3 Carbonyl Condensation Reactions versus Alpha-Substitution Reactions
p 884
23.4 Dehydration of Aldol Products: Synthesis of Enones p 885
23.5 Recognizing Aldol Products p 887
23.6 Mixed Aldol Reactions p 888
23.7 Intramolecular Aldol Reactions p 888
23.8 Reactions Similar to the Aldol Condensation p 890
23.9 The Claisen Condensation Reaction p 891
23.10 Mixed Claisen Condensations p 893
23.11 Internal Claisen Condensations: the Dieckmann Cyclization p 896
23.12 The Michael Reaction
23.13 The Stork Enamine Reaction p 901
23.14 Carbonyl Condensation Reactions in Synthesis: The Robinson Annulation
Reaction p 904
23.15 Biological Carbonyl Condensation Reactions p 906
Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions
30.1 Some Examples of Pericyclic Reactions p 1149
30.2 Atomic and Molecular Orbitals p 1151
30.3 Molecular Orbitals of Conjugated Pi Systems p 1153
30.4 Molecular Orbitals and Pericyclic Reactions p 1154, Notes
30.5 Electrocyclic Reactions p 1157
30.6 Stereochemistry of Thermal Electrocyclic Reactions p 1160
30.7 Photochemical electrocyclic reactions p 1162
30.8 Cycloaddition Reactions p 1165, Notes
30.9 Stereochemistry of Cycloadditions p 1167
30.10 Sigmatropic Rearrangements p 1171
30.11 Stereochemistry of Sigmatropic Rearrangements p 1172
30.12 Some Examples of Sigmatropic Rearrangements p 1173
30.13 A Summary of Rules for Pericyclic Reactions p 1177
Chapter 24: Carbohydrates
24.1 Classification of Carbohydrates p 915
24.2 Fischer Projections for Depicting Carbohydrates p 918
24.3 D. L. Sugars p 920
24.4 Configurations of the Aldoses p 922
24.5 Cyclic Structures of Monosaccharides: Hemiacetal Formation p 924
24.6 Monosaccharide Anomers: Mutarotation p 927
24.7 Conformations of Monosaccharides p 928
24.8 Reactions of Monosaccharides p 930
24.9 Stereochemistry of Glucose: The Fischer Proof p 940
24.10 Disaccharides p 944
24.11 Polysaccharides p 947
24.12 Other Important Carbohydrates p 949
24.13 Carbohydrates on Cell Surfaces p 950
Chapter 26: Arylamines and Phenols
26.1 Basicity of Arylamines p 1001
26.2 Preparation of Arylamines p 1004
26.3 Reactions of Arylamines p 1005
26.4 Phenols p 1012
26.5 Industrial Uses of Phenols p 1012
26.6 Properties of Phenols: Acidity p 1014
26.7 Preparation of Phenols p 1018
26.8 Reactions of Phenols p 1019
26.9 Spectroscopy of Arylamines and Phenols p 1024
Chapter 27: Amino Acids, Peptides, and Proteins
27.1 Structures of Amino Acids p 1037
27.2 Dipolar Structure of Amino Acids p 1041
27.3 Isoelectric Point p 1042
27.4 Synthesis of a-Amino Acids p 1045
27.5 Resolution of R,S Amino Acids
27.6 Peptides p 1049
27.7 Covalent Bonding in Peptides p 1051
27.8 Peptide Structure Determination: Amino Acid Analysis p 1052
27.9 Peptide Sequencing: The Edman Degradation p 1054
27.10 Peptide Sequencing: C-Terminal Residue Determination p 1057
27.11 Peptide Synthesis p 1057
27.12 Automated Peptide Synthesis: The Merrifield Solid-Phase Technique
p 1061
27.13 Calssification of Ptoteins p 1063
27.14 Protein Structure p 1065
27.15 Enzymes p 1069
27.16 Protein Denaturation p 1071
Chapter 28: Lipids
28.1 Waxes, Fats, and Oils p 1079
28.2 Soaps p 1083
28.3 Phospholipids p 1085
28.4 Biosynthesis of Fatty Acids p 1086
28.5 Prostaglandins p 1089
28.6 Terpenes p 1090
28.7 Biosynthesis of Terpenes p 1093
28.8 Steroids p 1095
28.9 Stereochemistry of Steroids p 1098
28.10 Steroid Biosynthesis p 1100
Chapter 29: Heterocycles and Nucleic Acids
29.1 Five-Membered Unsaturated Heterocycles p 1108
29.2 Structures of Pyrrole, Furan, and Thiophene p 1109
29.3 Electrophilic Substitution Reactions of Pyrrole, Furan and Thiopene
p 1110
29.4 Pyridine, a Six-Membered Heterocycle p 1112
29.5 Electrophilic Substitution of Pyridine p 1113
29.6 Nucleophilic Substitution of Pyridine p 1114
29.7 Fused-Ring Heterocycles p 1115
29.8 Pyrimidine and Purine p 1117
29.9 Nucleic Acids and Nucleotides p 1117
29.10 Structure of DNA p 1121
29.11 Base pairing in DNA: The Watson-Crick Model p 1122
29.12 Nucleic Acids and Heredity p 1125
29.13 Replication of DNA p 1125
29.14 Structure and Synthesis of RNA: Transcription p 1128
29.15 RNA and Protein Biosynthesis: Translation p 1130
29.16 Sequencing of DNA p 1134
29.17 Laboratory Synthesis of DNA p 1141
Chapter 31: Synthetic Polymers
31.1 General Classes of Polymers p 1186
31.2 Radical Polymerization of Alkenes p1187
31.3 Cationic Polymerization p 1189
31.4 Anionic Polymerization p1191-1192
31.6 Stereochemistry of Polymerization: Ziegler-Natta Catalysts p 1193
31.7 Diene Polymers: Natural and Synthetic Rubbers p 1195
31.8 Copolymers p 1197
31.9 Step-Growth Polymers: Nylon p 1199
31.10Polyesters p 1201
31.11 Polyurethanes p 1202
31.12 Polymer Structure and Chemistry p 1204
31.13 Polymer Structure and Physical Properties p 1205