Contents Preface.xi Author. xiii Common Abbreviations.xv Chapter 1 Fundamental Principles of Organic Chemistry.1 1.1 Bonding and Orbitals.1 1.2 Ionic versus Covalent Chemical Bonds.
2 1.3 Breaking Covalent Bonds.3 1.4 Polarized Covalent Ï-Bonds.4 1.5 Reactive Intermediates.5 1.6 Alkanes and Isomers.
7 1.7 The IUPAC Rules of Nomenclature.8 1.8 Rings Made of Carbon: Cyclic Compounds. 11 1.9 Hydrocarbon Functional Groups. 11 1.10 Heteroatom Functional Groups.
13 1.10.1 C--X Type Functional Groups. 13 1.10.2 C=X Type Functional Groups. 17 1.11 Hydrogen-Bonding and Solubility.
21 1.12 Rotamers and Conformation.24 1.13 Conformations with Functional Groups.30 1.14 Conformation of Cyclic Molecules. 31 1.15 Stereogenic Carbons and Stereoisomers.
37 1.16 Absolute Configuration [( R) and ( S) Nomenclature]. 39 1.17 Specific Rotation.44 1.18 Diastereomers.46 1.19 Alkene Stereoisomers: ( E ) and ( Z )-Isomers.
51 Homework.54 Chapter 2 The Importance of Water in Biochemical Systems. 55 2.1 Hydrogen Bonding. 55 2.2 Solubility. 58 2.3 Water Molecules in Biological Systems.
59 2.4 Acid-Base Equilibria in Water. 61 2.5 Buffers.65 2.6 Structural Features That Influence Acid Strength.66 2.7 Acid and Base Character of Alcohols, Thiols, Amines and Carbonyls.
67 2.7.1 Acids. 67 2.7.2 Bases.69 2.8 Elimination Reactions of Alkyl Halides (E2 and E1 Reactions).
71 2.9 Acid-Base Equilibria in Amino Acids. 74 2.10 Directionality. 78 Homework.80 Chapter 3 Nucleophiles and Electrophiles.83 3.1 Nucleophiles and Bimolecular Substitution (the SN2 Reaction).
83 3.2 Nucleophilic Substitution with Alcohols, Ethers, Amines, or Phosphines.85 3.3 Carbocations and the SN1 Reaction.88 3.4 Ethers and Thioethers as Nucleophiles.90 3.5 Chemical Reactions of Carbonyl Groups.
93 3.6 Biochemical Reactions of Ketones and Aldehydes.96 3.7 Carboxylic Acid Derivatives and Acyl Substitution.97 3.8 Biological Hydrolysis. 102 Homework. 106 Chapter 4 Radicals.
109 4.1 Structure of Radicals. 109 4.2 Formation of Radicals in Organic Chemistry. 110 4.3 Reactions of Radicals. 111 4.4 Formation of Radicals in Biological Systems.
112 4.5 Radicals in Biological Systems. 114 4.6 Radical Reactions in Biochemical Systems. 116 4.7 Radicals and Cancer. 118 Homework. 119 Chapter 5 Dienes and Conjugated Carbonyl Compounds in Biochemistry.
121 5.1 Conjugated Dienes and Conjugated Carbonyl Compounds. 121 5.2 Reactions of Conjugated Compounds.124 5.3 Conjugate (Michael) Addition. 127 5.4 Enzyme-Mediated Conjugate Additions.
128 5.5 Sigmatropic Rearrangement Reactions. 129 5.6 Enzyme-Mediated Sigmatropic Rearrangements. 132 Homework. 133 Chapter 6 Enolates and Enolate Anions. 135 6.1 Aldehydes and Ketones Are Weak Acids.
135 6.2 Formation of Enolate Anions. 136 6.3 The Aldol Condensation. 137 6.4 Enzyme-Mediated Aldol Condensations. 138 6.5 The Claisen Condensation.
141 6.6 Enzyme-Mediated Claisen Condensation. 142 6.7 Decarboxylation. 143 Homework. 144 Chapter 7 Enzymes. 147 7.1 Enzyme Kinetics.
147 7.1.1 Kinetics in Organic Chemistry. 147 7.1.2 Catalysts and Catalytic Reactions. 149 7.1.
3 Enzyme Kinetics. 149 7.2 Enzymes and Enzyme Classes. 153 7.3 Oxidoreductases (EC 1). 157 7.3.1 Chemical Oxidation of Alcohols.
157 7.3.2 Oxidases.