李艳梅有机化学课件第六章.ppt

Chapter6

;Content;6.1.1Classification

6.1.2Nomenclature

6.1.3Isomers(learnonyourown);6.1.1Classification;Tertiaryhaloalkane;6.1.2Nomenclature;IUPACnomenclature;(1R,3S)-1-chloro-3-methylcyclohexane;6.1.3Isomers(learnonyourown);6.2.1Physicalproperties

6.2.2spectrumdata

11H-NMR

213C-NMR

3IR;1H-NMR;;13C-NMR;IR;6.3.1Structureandinductiveeffect

6.3.2Nucleophilicsubstitution

6.3.3Elimination

6.3.4Reactionwithmetals

6.3.5Reduction;1,Structureofalkylhalides卤代烷的结构;2,Dipolemoment偶极矩;3,Inductiveeffect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;InductedDynamicNuclearPolarization;C;Easiertobreak;?＋;6.3.2Nucleophilicsubstitution;RX;Typicalexamplesofnucleophilicsubstitution一些典型实例;2,Abovereactionsappliedtosynthesis;3,Reactionsbelowareoftenimpliedinidentifying;Polarizability;RI;反应速度：

RIRBrRClRF

苯甲型、烯丙型、30RX20RX10RX卤苯型、乙烯型;6.3.3Elimination消去（消除）反应;Eliminationoccurswhenthehydrogenatomandthehalogenatomareonthesameplane,butondifferentsidesoftheC-Cbond.

消去反式共平面的氢原子;;Whichkindofhydrogenatomsarepreferred?;消除反应与取代反应常同时发生：;6.3.4Reactionwithmetals;1)ReactionwithMg;;乙醚的作用：;???;Forsomestablehalides;PropertiesofGrignardreagent;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;2021/5/9;2)ReactionwithNa;3)ReactionwithLi;6.3.5Reduction;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。;6.4.1Twomechanisms

6.4.2FactorsWhichEffecttheTwoMechanism

;6.4.1Twomechanisms;1,SN2mechanism;;2,SN1mechanism;Potentialenergy;;NomenclatureClassification命名与分类;?-phyperconjugation

?-p超共轭;Unstablecarbocation;;2021/5/9;碳正离子与SN1反应的立体化学;ExperimentalResult;WinsteinS.;6.4.2FactorsWhichEffecttheTwo