第三章 单烯烃 (6学时)修改版.ppt

Classification of Olefines 烯烃的种类 Contents 3.1 Structure of Alkenes 3.2 Isomerism and nomenclature 3.3 Physical properties of alkenes 3.4 Chemical properties of alkenes 3.5 inductive effect 3.6 Mechanism of electrophilic addition 3.7 ethene and propene 3.8 Preparation of alkene 3.9 Fossil oil Calculating the Degree of Unsaturation（不饱和度） Bonding in Ethylene 3-D Molecules: Cis and trans isomers can be interconverted 3.4 The Chemical Properties of Alkenes烯烃的化学性质 In a dilute acid medium, Markovnikov’s rule is followed Mechanism for Halohydrin Formation Regioselectivity What will thess reactions give? The mechanism of the oxidation reaction Syn-addition Syn addition versus anti addition syn addition : two atoms or groups add to the same face of a double bond. anti addition: two atoms or groups add to opposite faces of the double bond, the process is called The relative energy levels (stabilities) of three alkenes that can be catalytically hydrogenated to 2-methylbutane mechanism for cis glycol formation Remember the product is cis-diol The addition of oxygen to an alkene is a stereospecific reaction. Summary of the Methods Used to Oxidize an Alkene 作 业 P79-81 2，3,4，6，7，10，11，12，15, 17, 21 硼氢化--氧化反应的应用 *1 CH3CH=CH2 B2H6 H2O2， HO- H2O CH3CH2CH2OH *2 B2H6 H2O2， HO- H2O 反应的总结果：烯烃与水的加成，反马氏规则 *1 CH3CH=CH2 B2H6 H2O2， HO- H2O CH3CH2CH2OH *2 B2H6 H2O2， HO- H2O *3 B2H6 H2O2， HO- H2O *3 后面讲 硼氢化－氧化反应 (hydroboration/oxidation) Summary of Alcohol Synthesis from Alkenes P 296 5. 羟汞化－脱汞反应 Addition of Water to Alkenes: Oxymercuration 反应的总结果：烯烃与水的加成，符合马氏规则。 反应的特点： *1 高区域选择性—符合马氏规则（high regioselectivity） *2 反应速率快，条件温和，是实验室制备醇的一种方法 。 *3 没有重排产物产生。 Mechanism of Oxymercuration 6. 与烯烃的加成 (查资料完成) 加成反应机理：生成碳正离子中间体 (Carbocation) β-消除 Why? 二、烯烃的自由基加成反应 Radical Addition P57. 过氧化物效应(卡拉施Kharasch效应)： 当有过氧化物（Peroxide如 H2O2, R-O-O-R等）存在时，不对称烯烃与HBr的加成产