新版2月6日第9章 卤代烃2018revised培训资料.ppt

第九章 卤代烃;Content; 9.1.1 Classification 9.1.2 Nomenclature 9.1.3 Isomers (learn on your own); 9.1.1 Classification（分类）;问题：苄基溴是什么类型的卤代烃？;Tertiary halo alkane;9.1.2 Nomenclature (命名);IUPAC nomenclature;9.1.3 Isomers (learn on your own);课堂练习; 9.3.1 Structure and inductive effect 9.3.2 Nucleophilic substitution 9.3.3 Elimination 9.3.4 Reaction with metals 9.3.5 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;?＋;9.3.2 Nucleophilic substitution（亲核取代）;RX;Typical examples of nucleophilic substitution 一些典型实例;2, Above reactions applied to synthesis;3, Reactions below are often implied in identifying ;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;9.3.3 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：;9.3.4 Reaction with metals (与金属的反应);1) Reaction with Mg;1912 Nobel prize for chemistry ;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;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; 9.3.5 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。; 9.4.1 Two mechanisms 9.4.2 Factors Which Effect the Two Mechanism ;9.4.1 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.;9.4.2 Factors Which Effect the Two Mechanism;(A) Effects of Alkyl Groups （烷基）;SN1;Other Alkyl Groups 其它烷基:;SN1 and SN2 mechanisms are both favorable;Neither SN1 n