第一章 有机化合物分子的 结构基础第一章重点讲解问题n1. 简要回顾有机化学的形成，并回答有机化学是 怎样的一门学科n2. 价键理论基础回顾和分子轨道理论简介n3. 杂化轨道理论与有机化合物结构特点n4. 有机化合物的基本骨架和官能团n5. 有机化合物的结构与性质的关系n 1、价键 2、非共价力 3、立体结构 n6. 质子酸碱和路易斯酸碱理论1.1 有机化学及其发展历史和趋势n1. HistorynIn 1770, Swedish chemist Torberm Bergman was the first to express the difference between “organic” and “inorganic”substances1.1 有机化学及其发展历史和趋势nOrganic -n derived from living organismnOriginally, nStudy of compounds extracted from living organisms and their natural products 1.1 有机化学及其发展历史和趋势nVital force theory: nOrganic compounds needs a “vital force” to create them1.1 有机化学及其发展历史和趋势nIn 1828, Fridrich Wohler convert the “inorganic” salt ammonium cyanate into the “organic” substance urea1.1 有机化学及其发展历史和趋势nWohlers synthesis led to the realization that molecules found in nature can be described, handled, and synthesized in the same way as minerals and metals. What an astounding insight-that atoms and molecules move freely between the living and nonliving worlds, that the living and nonliving share fundamental attributes that can be studied. With this discovery, organic chemistry was born.1.1 有机化学及其发展历史和趋势n作业 1：n查阅有关书籍和文献，了解有机化学的发展历史和趋势。并就发展历史中可以称之为里程碑的一个发现作介绍和评述。n字数要求在1500字以内,第六周周三交1.1 有机化学及其发展历史和趋势n2. Definition of Organic ChemistrynOrganic Chemistry is the Chemistry of Carbon Compounds Organic Chemistry is the Chemistry of Carbon CompoundsnQuestion: nWhy is an entire branch of chemistry devoted to the study of carbon- containing compounds?Organic Chemistry is the Chemistry of Carbon CompoundsnThe answer is :nCarbon-containing compounds makes life possiblenWe need carbon-containing compounds in nature for our food, medicines, clothing, and energynWe depend on millions of synthetic carbon -contaning compounds in our daily lifeOrganic Chemistry is the Chemistry of Carbon CompoundsnQuestion: nWhat makes carbon so special?nWhy are there so many carbon- containing compounds?Organic Chemistry is the Chemistry of Carbon CompoundsnPlease try to draw out all the structures corresponding to the formula: na. C2H6Onb. C3H6OnIt shares electrons with other carbon atoms nIt shares electrons with several kinds of atomsnC-C single, double and triple bondnchain, or cyclo-links nIsomerism phenomenon1.2 价键理论基础回顾和分子轨道 理论简介n1.2.1 The Structure of an Atomn1.2.2 Distribution of Electrons in an Atom nAtomic orbitals: 1.2 价键理论基础回顾和分子轨道 理论简介n(1) The aufbau priciplenThe closer the orbital is to the nucleus, the lower its energyn1s2s2p3s3p4s3d4p5s4d5p6sn(2) The Pauli exclusion priciplenDegenerate orbitals - have the same energyn(3) Hunds rulenC: 1s2 2s2 2px12py12pz01.2 价键理论基础回顾和分子轨道 理论简介n1.2.3 Ionic, Covalent, and Polar BondsnAn atom is most stable if it has a filled shell or an outer shell of eight electrons and no electrons of higher energynIonic bond: LiClnCovalent bond: H2, O2, CO2 n C: 1s2 2s2 2px12py12pz0n Neither readily gives up electrons n Nor readily accepts electronsnNonpolar bond (H-H)and Polar bond ( C-H, C-O )1.2 价键理论基础回顾和分子轨道 理论简介n常见价键的表示方法：nLewis StructuresnKekule StructuresnCondensed StructuresHCO2H1.2 价键理论基础回顾和分子轨道 理论简介n思考题n共价键化合物与离子键化合物性质有哪些差异？n请记住有机化合物中常见元素的电负性nElectronegativity:nH: 2.1 B: 2.0 C: 2.5 N: 3.0 O: 3.5nF: 4.0 Cl: 3.0 Br: 2.8 I: 2.5nLi: 1.0 Mg: 1.21.2 价键理论基础回顾和分子轨道 理论简介n1.2.4 Introduction of Molecular TheorynOrbitals are conserved - the number of atomic orbitals combined must equal the number of molecular orbitals formed1.2.4 Introduction of Molecular TheorynThe above only shows the bonding molecular orbital, the other one is antibonding molecular orbital, but it contains no electrons.1.2.4 Introduction of Molecular TheorynThe 1s atomic orbitals can combine in one of two ways1.2.4 Introduction of Molecular Theoryn- The 1s atomic orbitals combine in a way that enhance each other, similar to two light waves or two sound waves that reinforce each other. It is a sigma bonding molecular orbital 键 n- The 1s atomic orbitals can also combine in a way that cancel each other, producing a node between the nuclei. It is a sigma antibonding molecular orbital * 键 1.2.4 Introduction of Molecular TheorynSide-to-side overlapping of in-phase p orbitals produces a bonding pi- molecular orbital 键 nSide-to-side overlapping of out-of- phase p orbitals producing an antibonding pi- molecular orbital * 键 1.3 碳的杂化轨道理论Hybridizationn1.3.1 sp3 HybridizationnC 1s22s22p2 - 2s22px12py12pz0 2s12px12py12pz1 n2s + 2px2py2pz 4 sp3 hybridization orbitals neach orbital has one electron 1.3.1 sp3 Hybridizationn to form a tetrahedron carbon (see the structure of methane)1.3.1 sp3 HybridizationnConfiguration isomers - enantiomersn a chiral carbon - a carbon linked with four different kinds of atomsnConformation isomer - ethane1.3.2 sp2 HybridizationnC 1s22s22p