李艳梅有机化学第六章概念.ppt

Alkyl halides 第六章 卤代烷;Content; 6.1.1 Classification 6.1.2 Nomenclature 6.1.3 Isomers (learn on your own); 6.1.1 Classification;Tertiary halo alkane;6.1.2 Nomenclature;IUPAC nomenclature;(1R,3S)-1-chloro-3-methylcyclohexane;6.1.3 Isomers (learn on your own);6.2.1 Physical properties 6.2.2 spectrum data 1 1H-NMR 2 13C-NMR 3 IR; 1H-NMR;X; 13C-NMR; IR; 6.3.1 Structure and inductive effect 6.3.2 Nucleophilic substitution 6.3.3 Elimination 6.3.4 Reaction with metals 6.3.5 Reduction;1, Structure of alkyl halides 卤代烷的结构;2, Dipole moment 偶极矩;3, Inductive effect 诱导效应;;CH3;表示法;Y;－I 效应的强度;1、钥原子电负性越强， 吸电子能力越强， －I 效应越强;sp;＋I 效应的强度;动态诱导效应;4, Polarizability 分子的极化 ;Inducted Dynamic Nuclear Polarization;C;Easier to break;?＋;6.3.2 Nucleophilic substitution;H2O;Typical examples of nucleophilic substitution 一些典型实例;应用于合成 RX为“良好的烷基化试剂”;应用于鉴别;Polarizability;RI;反应速度： RI RBr RCl RF 苯甲型、烯丙型、30RX 20RX 10RX 卤苯型、乙烯型;6.3.3 Elimination 消去（消除）反应;Elimination occurs when the hydrogen atom and the halogen atom are on the same plane, but on different sides of the C-C bond. 消去反式共平面的氢原子;Which kind of hydrogen atoms are preferred?;消除反应与取代反应常同时发生：;6.3.4 Reaction with metals;1) Reaction with Mg;;乙醚的作用：; ???;For some stable halides;Properties of Grignard reagent;格氏试剂性质之一：与卤代烃反应;RX + Mg + Ether(abs.);格氏试剂性质之二：与含活泼氢的化合物反应;坏处： 制备格氏试剂时要求绝对无水、无醇（无含活泼氢的溶剂） 做合成题时也应高度注意 ！ ;格氏试剂性质之三：与O2、CO2反应;2) Reaction with Na;3) Reaction with Li; 6.3.5 Reduction;氢解：用催化氢化法使碳与杂原子（O，N，X等）之间的键断裂 苯甲位的碳与杂原子之间的键很易氢解。; 6.4.1 Two mechanisms 6.4.2 Factors Which Effect the Two Mechanism ;6.4.1 Two mechanisms;1, SN2 mechanism;;2, SN1 mechanism;Potential energy;; Nomenclature Classification 命名与分类;?-p hyper conjugation ?-p 超共轭;Unstable carbocation;; 碳正离子与SN1反应的立体化学;Experimental Result;Winstein S.;6.4.2 Factors Which Effect the Two Mechanism;(A) Effects of Alkyl Groups;SN1;Other Alkyl Groups 其它烷基:;S