【正文】 《有機(jī)化學(xué)》課程講義（適用于化學(xué)教育、應(yīng)用化學(xué)、化學(xué)工程專業(yè)）溫梅姣 編寫教 化學(xué)與資源環(huán)境學(xué)院二〇一〇年七月1Organic ChemistryContentsChapter 1 Introduction………………………………………………………………1 The development of Organic Chemistry as a science………………………1 The importance of Organic Chemistry………………………………………1 How to study Organic Chemistry……………………………………………2 Covalent Bonding amp。 Shapes of Molecules…………………………………3 Polar and Nonpolar Molecules………………………………………………5 Resonance……………………………………………………………………6 Molecular Orbital Theory……………………………………………………8 Hybrid Orbitals………………………………………………………………9Chapter 2 Alkane and cycloalkane…………………………………………………13 Alkane………………………………………………………………………13 Nomenclature of Cycloalkanes……………………………………………17 Conformations………………………………………………………………18 Oxidation of Alkanes………………………………………………………24 Chlorination and Bromination of Alkanes…………………………………25Chapter 3 Alkene……………………………………………………………………29 Structure and nomenclature…………………………………………………29 Reaction Mechanism………………………………………………………32 Reaction of Alkene…………………………………………………………35Chapter 4 Alkyne and Diene…………………………………………………………47 Structure and Nomenclature of Alkynes……………………………………47 Physical Properties of Unsaturated Hydrocarbons…………………………48 addition reaction of alkyne…………………………………………………48 An Introduction to Multistep Synthesis……………………………………54 Preparation Of Alkyne………………………………………………………54 Properties and nomenclature of Dienes……………………………………55 Reaction of dienes…………………………………………………………57Chapeter 5 Stereochemistry…………………………………………………………60 Isomers……………………………………………………………………60 Isomers with One Asymmetric Carbon……………………………………61 Isomers with More than One Asymmetric Carbon………………………64 resolution of a racemic mixture……………………………………………65 Stereochemistry of Reactions: Regioselective, Stereoselective, and Stereospecific Reactions………………………………………………………66Chapter 6 Aromatic hydrocarbons…………………………………………………70 The structure of benzene…………………………………………………70 Substitued derivatives of benzene and their nonmenclature………………72 polycyclic aromatic hydrocarbons………………………………………74 Criteria for Aromaticity…………………………………………………74 Electrophilic aromatic substitution reaction………………………………75 Reactions of Substituted Benzenes………………………………………80 Reactions of Substituents on Benzene……………………………………86Chapter 7 Alkyl Halides……………………………………………………………89 Nomenclature of Alkyl Halides……………………………………………897. 2 Classes of Alkyl Halides…………………………………………………897. 3 Bonding in Alkyl Halides…………………………………………………89 Physical properties of alkyl halides…………………………………………90 Substitution Reactions of Alkyl Halides……………………………………91 Elimination Reactions of Alkyl Halides…………………………………100Chapter 8 Alcohols and ethers………………………………………………………108 Nomenclature of Alcohols…………………………………………………108 Bonding in Alkyl Halides…………………………………………………108 Physical properties of alcohols……………………………………………109 Acidity and Basicity of alcohols…………………………………………110 Substitution Reactions of Alcohols………………………………………111 Elimination Reactions of Alcohols s………………………………………114 Substitution Reactions of Ethers…………………………………………116 Reactions of Epoxides……………………………………………………117Chapter 9 Infrared Spectroscopy and NMR Spectroscopy…………………………120 Infrared Spectroscopy……………………………………………………120 Nuclear Magnetic Resonance……………………………………………127Chapter 10 Aldehydes and Ketones…………………………………………………139 Nomenclature……………………………………………………………139 Structure and bonding: The carbonyl group……………………………140 Physical Properties………………………………………………………141 Sources of Aldehydes and Ketones………………………………………141 Nucleophilic Addition……………………………………………………142 Oxidation of aldehydes…………………………………………………147 Enols and Enolates………………………………………………………150Chapter 11 Carboxylic Acids………………………………………………………157 Nomenclature of Carboxylic Acids………………………………………157 Structure and bonding……………………………………………………157 Physical properties s……………………………………………………158 Acidity of Carboxylic Acids……………………………………………158 Salts of Carboxylic acids…………………………………………………159 Substituents and Acid Strength…………………………………………160 Ionization of Substituted Benzoic acids…………………………………161 Souces of Carboxylic Acids……………………………………………162 Reactions of Carboxylic Acids…………………………………………162Chapter 12 Carboxylic Acid Derivatives……………………………………………166 Nomenclature of all carboxylic acid derivatives…………………………166 The structures of carboxylic acid derivatives……………………………167 Nucleophilic Substitution in Acyl Chlorides……………………………168 Nucleophilic Substitution in Carboxylic acid anhydrides………………169 Nucleophilic Substitution in Esters………………………………………170 Reaction of Amides………………………………………………………172 Nitriles……………………………………………………………………174 Ester enolates……………………………………………………………175Chapter 13 Amines…………………………………………………………………182 Amines Nomenclature……………………………………………………182 Structure and Bonding……………………………………………………183 Physical Properties………………………………………………………184 Basicity of Amines………………………………………………………185 Tetraalkyl Ammonium Salts as phasetransfer catalyst…………………185 Preparation of Amines……………………………………………………186 Reactions of Amines……………………………………………………188 IV Chapter 1 Introduction The development of Organic Chemistry as a science The history of Organic Chemistry：(1) The Swedish chemist Torbern Bergman was the first person to express this difference between ‘Organic’ and ‘Inorganic’ substance in 1770. (2) In 1807, J246。ns Jakob Berzelius gave names to the two kinds of materials. Compounds derived from living organisms were believed to contain an unmeasurable vital force—the essence of life. These he called ‘inorganic’. Compounds derived from mineralsthose lacking that vital forcewere “inorganic”.(3) In 1816, Michel Chevreul found that soap, prepared by the reaction of alkali with animal fat, could be separated into several pure organic pounds, which he termed fatty acid. For the first time, one organic substance (fat) was converted into others (fatty acids plus glycerin) without