目录 1Bonding and Isomerism(键合和异构) 001 2Alkanes and Cycloalkanes; Conformational and Geometric Isomerism (烷烃和环烷烃;构象和几何异构) 031 3Alkenes and Alkynes(烯烃和炔烃) 054 4Aromatic Compounds(芳香化合物) 094 5Stereoisomerism(立体异构) 119 6Organic Halogen Compounds; Substitution and Elimination Reactions (含卤有机化合物;取代反应和消除反应) 143 7Alcohols, Phenols, and Thiols(醇,酚和硫醇) 162 8Ethers and Epoxides(醚和环氧化合物) 184 9Aldehydes and Ketones(醛和酮) 200 10Carboxylic Acids and Their Derivatives(羧酸及其衍生物) 230 11Amines and Related Nitrogen Compounds(胺和相关含氮化合物) 263 12Spectroscopy and Structure Determination(波谱学和结构测定) 287 13Heterocyclic Compounds(杂环化合物) 315 14Synthetic Polymers(合成高聚物) 331 15Lipids and Detergents(脂类和洗涤剂) 350 16Carbohydrates(糖类) 368 17Amino Acids, Peptides, and Proteins(氨基酸,肽和蛋白质) 394 18Nucleotides and Nucleic Acids(核苷酸和核酸) 419 Contents 1Bonding and Isomerism(键合和异构) 001 1.1How Electrons Are Arranged in Atoms(原子中的电子排布) 002 1.2Ionic and Covalent Bonding(离子键和共价键) 003 1.3Carbon and the Covalent Bond(碳原子和共价键) 006 1.4Carbon?CCarbon Single Bonds(碳-碳单键) 007 1.5Polar Covalent Bonds(极性共价键) 008 1.6Multiple Covalent Bonds(多重共价键) 010 1.7Valence(化合价) 011 1.8Isomerism(异构现象) 011 1.9Writing Structural Formulas(结构式的书写) 012 1.10Abbreviated Structural Formulas(简化结构式) 014 1.11Formal Charge(形式电荷) 016 1.12Resonance(共振理论) 017 1.13Arrow Formalism(箭头形式) 018 1.14The Orbital View of Bonding; the Sigma Bond (共价键的轨道理论;σ键) 019 1.15Carbon sp3 Hybrid Orbitals(碳的sp3杂化轨道) 020 1.16Tetrahedral Carbon; the Bonding in Methane(碳原子的四面体结构;甲烷分子中的碳氢键) 022 1.17Classification According to Molecular Framework (按分子骨架分类) 023 1.18Classification According to Functional Group(按功能基分类) 026
2Alkanes and Cycloalkanes; Conformational and Geometric Isomerism(烷烃和环烷烃;构象和几何异构) 031 2.1The Structures of Alkanes(烷烃的结构) 032 2.2Nomenclature of Organic Compounds(有机化合物的命名) 033 2.3IUPAC Rules for Naming Alkanes(烷烃的IUPAC命名规则) 034 2.4Alkyl and Halogen Substituents(烷基和卤素取代基) 036 2.5Use of the IUPAC Rules(IUPAC命名规则的应用) 037 2.6Sources of Alkanes(烷烃的来源) 038 2.7Physical Properties of Alkanes and Nonbonding Intermolecular Interactions(烷烃的物理性质和分子间的非键作用) 038 2.8Conformations of Alkanes(烷烃的构象) 040 2.9Cycloalkane Nomenclature and Conformation (环烷烃的命名和构象) 041 2.10Cis-Trans Isomerism in Cycloalkanes(环烷烃的顺反异构) 045 2.11Summary of Isomerism(异构现象小结) 046 2.12Reactions of Alkanes(烷烃的化学反应) 046 2.13The Free-Radical Chain Mechanism of Halogenation (烷烃卤代的自由基链反应机制) 049
3Alkenes and Alkynes(烯烃和炔烃) 054 3.1Definition and Classification(定义和分类) 055 3.2Nomenclature(命名) 056 3.3Some Facts about Double Bonds(碳碳双键的特征) 058 3.4The Orbital Model of a Double Bond; the Pi Bond(碳碳双键的轨道模型;π键) 059 3.5Cis?CTrans Isomerism in Alkenes(烯烃的顺反异构现象) 061 3.6Addition and Substitution Reactions Compared(加成和取代反应的比较) 065 3.7Polar Addition Reactions(极性加成反应) 065 3.8Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov’s Rule(不对称试剂与不对称烯烃的加成;马尔可夫尼可夫规则) 067 3.9Mechanism of Electrophilic Addition to Alkenes(烯烃的亲电加成机制) 069 3.10Markovnikov’s Rule Explained(马尔可夫尼可夫规则的解释) 070 3.11Reaction Equilibrium: What Makes a Reaction Go? (反应平衡:什么使反应能够进行下去?) 072 3.12Reaction Rates: How Fast Does a Reaction Go?(反应速率:反应进行得有多快?) 073 3.13Hydroboration of Alkenes(烯烃的硼氢化反应) 075 3.14Addition of Hydrogen(加氢反应) 077 3.15Additions to Conjugated Systems(共轭烯烃的加成反应) 078 3.16Free-Radical Additions; Polyethylene (自由基加成反应;聚乙烯) 081 3.17Oxidation of Alkenes(烯烃的氧化) 082 3.18Some Facts about Triple Bonds(叁键的特征) 084 3.19The Orbital Model of a Triple Bond(叁键的轨道模型) 084 3.20Addition Reactions of Alkynes(炔烃的加成反应) 084 3.21Acidity of Alkynes(炔烃的酸性) 086
4Aromatic Compounds(芳香化合物) 094 4.1Some Facts about Benzene(有关苯的实验事实) 095 4.2The Kekulé Structure of Benzene(苯的凯库勒结构式) 096 4.3Resonance Model for Benzene(苯的共振结构模型) 096 4.4Orbital Model for Benzene(苯的轨道模型) 097 4.5Symbols for Benzene(苯的结构表达式) 098 4.6Nomenclature of Aromatic Compounds(芳香族化合物的命名) 098 4.7The Resonance Energy of Benzene(苯的共振能) 101 4.8Electrophilic Aromatic Substitution(芳香亲电取代反应) 102 4.9The Mechanism of Electrophilic Aromatic Substitution(芳香亲电取代反应的机制) 103 4.10Ring-Activating and Ring-Deactivating Substituents (苯环的活化基和钝化基) 107 4.11Ortho,Para-Directing and Meta-Directing Groups (邻,对位定位基和间位定位基) 107 4.12The Importance of Directing Effects in Synthesis (定位效应在合成中的重要性) 111 4.13Polycyclic Aromatic Hydrocarbons(多环芳香烃) 112
5Stereoisomerism(立体异构) 119 5.1Chirality and Enantiomers(手性和对映异构体) 120 5.2Stereogenic Centers; the Stereogenic Carbon Atom (手性中心;手性碳原子) 121 5.3Configuration and the R-S Convention(R-S 构型) 124 5.4Polarized Light and Optical Activity(偏振光和光学活性) 127 5.5Properties of Enantiomers(对映异构体的性质) 129 5.6Fischer Projection Formulas(费歇尔投影式) 130 5.7Compounds with More Than One Stereogenic Center; Diastereomers(具有多个手性中心的化合物;非对映异构体) 132 5.8Meso Compounds; the Stereoisomers of Tartaric Acid(内消旋化合物;酒石酸的立体异构体) 134 5.9Stereochemistry: A Recap of Definitions(立体化学:定义概述) 135 5.10Stereochemistry and Chemical Reactions (立体化学和化学反应) 136 5.11Resolution of a Racemic Mixture(外消旋体的拆分) 138
6Organic Halogen Compounds; Substitution and Elimination Reactions(含卤有机化合物;取代反应和消除反应) 143 6.1Nucleophilic Substitution(亲核取代反应) 144 6.2Examples of Nucleophilic Substitutions(亲核取代反应实例) 144 6.3Nucleophilic Substitution Mechanisms(亲核取代反应机制) 147 6.4The SN2 Mechanism(双分子亲核取代机制) 147 6.5The SN1 Mechanism(单分子亲核取代机制) 149 6.6The SN1 and SN2 Mechanisms Compared(SN1和SN2反应 机制的比较) 151 6.7Dehydrohalogenation, an Elimination Reaction; the E2 and E1 Mechanisms(脱卤化氢,消除反应;双分子消除和单分子消除机制) 153 6.8Substitution and Elimination in Competition(取代反应和消除 反应的相互竞争) 154 6.9Polyhalogenated Aliphatic Compounds(多卤代脂肪烃) 156
7Alcohols, Phenols, and Thiols(醇,酚和硫醇) 162 7.1Nomenclature of Alcohols(醇的命名) 163 7.2Classification of Alcohols(醇的分类) 164 7.3Nomenclature of Phenols(酚的命名) 164 7.4Hydrogen Bonding in Alcohols and Phenols (醇和酚分子中的氢键) 165 7.5Acidity and Basicity Reviewed(酸性和碱性) 166 7.6The Acidity of Alcohols and Phenols(醇和酚的酸性) 168 7.7The Basicity of Alcohols and Phenols(醇和酚的碱性) 170 7.8Dehydration of Alcohols to Alkenes (醇脱水生成烯烃的反应) 170 7.9The Reaction of Alcohols with Hydrogen Halides (醇与卤化氢的反应) 172 7.10Other Ways to Prepare Alkyl Halides from Alcohols (由醇制备卤代烃的方法) 173 7.11A Comparison of Alcohols and Phenols(醇和酚的比较) 174 7.12Oxidation of Alcohols to Aldehydes, Ketones, and Carboxylic Acids(醇的氧化反应——生成醛,酮和羧酸) 174 7.13Alcohols with More Than One Hydroxyl Group(多元醇) 175 7.14Aromatic Substitution in Phenols(酚的芳香取代反应) 176 7.15Oxidation of Phenols(酚的氧化反应) 177 7.16Phenols as Antioxidants(酚类抗氧化剂) 177 7.17Tests for Phenols(酚的鉴别) 178 7.18Thiols, the Sulfur Analogs of Alcohols and Phenols (硫醇,醇和酚的硫类似物) 178
8Ethers and Epoxides(醚和环氧化合物) 184 8.1Nomenclature of Ethers(醚的命名) 185 8.2Physical Properties of Ethers(醚的物理性质) 186 8.3Ethers as Solvents(醚作溶剂) 186 8.4The Grignard Reagent; an Organometallic Compound(格利雅试剂;一种有机金属化合物) 187 8.5Preparation of Ethers(醚的制备) 189 8.6Cleavage of Ethers(醚的裂解) 190 8.7Epoxides (Oxiranes)[环氧化物(环氧乙烷)] 192 8.8Reactions of Epoxides(环氧化物的反应) 192 8.9Cyclic Ethers(环醚) 194
9Aldehydes and Ketones(醛和酮) 200 9.1Nomenclature of Aldehydes and Ketones(醛和酮的命名) 201 9.2Some Common Aldehydes and Ketones(常见的醛和酮) 202 9.3Synthesis of Aldehydes and Ketones(醛和酮的制备) 203 9.4Aldehydes and Ketones in Nature(天然醛酮) 204 9.5The Carbonyl Group(羰基) 205 9.6Nucleophilic Addition to
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