【正文】 …………………………………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。 these electrons are used to form chemical bonds and in chemical reactionsLewis dot structure: the symbol of an element represents the nucleus and all inner shell electronsdots represent valence electronsLewis Dot Structures for Elements 118 Lewis Model of BondingAtoms bond together so that each atom acquires an electron configuration the same as that of the noble gas nearest it in atomic numberan atom that gains electrons bees an anionan atom that loses electrons bees a cationthe attraction of anions and cations leads to the formation of ionic solidsan atom may share electrons with one or more atoms to plete its valence shell。orbital overlap pictures of methane, ammonia, and watersp2 Hybrid Orbitalsthe axes of the three sp2 hybrid orbitals lie in a plane and are directed toward the corners of an equilateral trianglethe unhybridized 2p orbital lies perpendicular to the plane of the three hybrid orbitalsBonding in Ethylenesp Hybrid Orbitalstwo lobes of unequal size at an angle of 180176。 carbonSecondary (2176。) C: a carbon bonded to three other carbons3176。) C: a carbon bonded to four other carbonsNomenclature IUPACParent name: the longest carbon chainSubstituent: a group bonded to the parent chain alkyl group: a substituent derived by removal of a hydrogen from an alkane。 all bonds on adjacent carbons are staggered Cyclohexane In a chair conformation, six H are equatorial and six are axial For cyclohexane, there are two equivalent chair conformationsall CH bonds equatorial in one chair are axial in the alternative chair, and vice versa Boat conformation: a puckered conformation of a cyclohexane ring in which carbons 1 and 4 are bent toward each otherthere are four sets of eclipsed CH interactions and one flagpole interaction a boat conformation is less stable than a chair conformation by 27 kJ ( kcal)/mol Twistboat conformationapproximately kJ ( kcal)/mol less stable than a chair conformation approximately kJ ( kcal)/mol more stable than a boat conformation Cis,Trans Isomers 1,2Dimethylcyclopentane