【大学有机化学知识点总结】大学有机化学知识点提纲

来源:名资汇网 作者:caiji007 2023-04-27 06:05:00
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  大学有机化学知识点提纲

  一)绪论

  共价键

  价键理论(杂化轨道理论);分子轨道理论;共振论.

  共价键的属性:键能;键长;键角;键的极性.

  键的极性和分子极性的关系;分子的偶极矩.

  有机化合物的特征

  (二)烷烃和环烷烃

  基本概念

  烃及其分类;同分异构现象;同系物;分子间作用力;a键,e键;构型,构象,构象分析,构象异构体;烷基;碳原子和氢原子的分类(即1,2,3碳,氢;4碳);反应机理,活化能.

  对于基本概念,不是要求记住其定义,而是要求理解它们,应用它们说明问题.

  命名

  开链烷烃和环烷烃的IUPAC命名,简单的桥环和螺环的命名.

  烷烃和环烷烃的结构

  碳原子sp3杂化和四面体构型;环烷烃的结构(小环的张力).

  烷烃的构象

  开链烷烃的构象,能量变化;环烷烃的构象:重点理解环己烷和取代环己烷的构象及能

  量变化,稳定构象,十氢萘及其它桥环的稳定构象.

  烷烃的化学性质

  自由基取代反应卤代反应及机理;碳游离基中间体结构,稳定性;不同的卤素在反应中的活性和选择性;反应过程中的能量变化.

  环烷烃的化学性质

  自由基取代反应(与烷烃一致);小环(3,4元环)性质的特殊性加成.

  (三)烯烃

  烯烃的结构特点

  碳的sp2杂化和烯烃的平面结构;键和键.

  烯烃的同分异构,命名

  碳架异构,双键位置异构,顺反异构(Z,E).

  烯烃的物理和化学性质

  烯烃的亲电加成及其机理,马氏规则;碳正离子中间体结构,稳定性,重排.

  其它加成反应:催化加氢(立体化学,氢化热);硼氢化氧化(加成取向,立体化学);羟汞化脱汞(加成取向);与HBr/过氧化物加成(加成取向);其它游离基加成.

  氧化反应:羟基化反应邻二醇的形成;KMnO4/H+的氧化,臭氧化反应,烯烃结构的测定.

  α-位取代反应:烯丙基型取代反应(高温卤代和NBS卤代)及机理烯丙基自由基.

  (四)炔烃和二烯烃

  炔烃

  ①结构:碳的sp杂化和碳-碳三键;sp杂化,sp2杂化和sp3杂化的碳的电负性的差异及相应化合物的偶极矩.

  ②同分异构体

  ③化学性质:末端炔烃的酸性及相关的反应;三键的加成:催化加氢,亲电加成,亲核加成;碳碳三键与H2/Lindlar催化剂反应(顺式烯烃);碳碳三键与Na/液氨的反应(反式烯烃);加卤素;加HX(马氏规则);加H2O(羰基化合物的形成);加HBr/过氧化物;硼氢化氧化;加HCN及乙炔的二聚;氧化反应:KMnO4氧化和臭氧化.

  二烯烃

  ①共轭二烯烃的稳定性:键能和键长平均化,共轭效应.

  ②二烯烃的化学反应:1,2-加成和1,4-加成(反应机理);反应的动力学控制和热力学控制(反应过程中的能量变化);烯丙型碳正离子的稳定性(p-共轭);Diels-Alder反应.

  (五)波谱分析

  紫外光谱

  理解各种跃迁(,n,,n)和各自的吸收能量波长;发色团和助色团;溶剂效应;最重要的是能够从一张UV谱图中得到有用的信息(判断结构)(不要求利用经验规则去计算某化合物之吸收波长).

  红外光谱

  理解IR光谱之基本原理,最重要的是利用IR光谱(结合其它波谱)推测有机分子的结构,这就要求对各类官能团的红外吸收范围有清楚的了解,并清楚影响峰位置变化的因素.

  核磁共振谱(1HNMR)(碳谱不要求)

  了解基本原理;基本概念:化学位移,内标,外标,偶合,偶合常数,屏蔽,去屏蔽等.清楚不同类型的枝质子的化学位移范围及影响因素;最重要的是利用NMR谱(结合其它波谱)推测有机分子的结构.

  质谱

  了解基本原理;几种重要的开裂方式(包括重要的重排开裂如麦氏重排,逆Diels-Alder重排等);最重要的是利用MS得出的分子离子峰(并结合其它波谱方法)推测有机分子的结构.

  本章最重要的是利用几种波谱方法结合推测有机分子的结构.

  (六)芳香烃

  苯的结构和芳香性

  理解芳香性的概念和判断芳香性的Hückel规则,能用此规则判断一给定的分子(或离子)是否是芳香性的.

  苯的异构,同系物和命名

  苯及其同系物的物理性质和波谱性质

  主要了解其波谱特征,例如芳香烃的NMR谱学特征,不同取代苯在IR指纹区的特征等.

  化学性质

  亲电取代反应及机理;傅氏反应的特点及局限;氯甲基化反应;Gatterman-Koch反应;芳香环上取代基的定位效应;其它反应:侧链氧化;侧链取代;芳香环上的还原:催化加氢,Birch还原.

  萘的结构和化学性质

  (七)立体化学

  基本概念

  对映异构(体);手性分子;镜像;旋光性,旋光度;对映体;非对映体;差向异构体;内消旋体;外消旋体;手征性;手性中心.

  对映异构体构型的表示法

  R/S法(次序规则).

  熟悉各类手性分子

  含13个手性碳原子的手性分子;不含手性碳原子的手性分子;环状化合物.

  立体异构体的制备和反应

  熟悉能产生立体异构体的化学反应及机理,象烯烃与卤素的反式加成,环氧乙烷的开环,羰基化合物的加成(Cram规则)等等.

  (八)卤代烃

  异构,分类,命名

  波谱性质,尤其是NMR谱

  化学性质

  亲核取代反应及机理(SN1,SN2);影响亲核取代及机理的因素;亲核试剂的亲核性;SN2反应的立体化学;SN1反应中的重排;邻基参与.

  消除反应及机理(E1,E2,E1cb):消除反应的取向(Saytzeff规则)和立体化学;消除反应和取代反应的竞争.

  卤代烃与Mg,Li,Na等的反应:Grignard试剂,有机锂试剂及其应用.

  (九)醇,酚,醚

  结构,分类,命名

  醇的物理性质和光谱性质

  氢键对其物理性质的影响;IR光谱和NMR谱的特征.

  醇的化学性质

  醇的酸性(与其它类型化合物如H2O,酚,羧酸酸性的比较);与酸性有关的反应(与金属如Na,Mg,Al的反应);醇的氧化(形成醛/酮,羧酸);熟悉各种氧化剂;醇的成酯反应:与无机酸成酯,与有机酸成酯(机理);卤化反应;用SOCl2卤化的立体化学及机理;用HX的卤代反应(Lucas试剂用来区别六个碳原子以下1,2和3醇);Wagner-Meerwein重排.

  醇的脱水反应:反应机理/扎依切夫规律;反应活性;重排;分子间脱水成醚.

  多元醇的反应:与HIO4或Pb(OAc)4的反应;片呐醇重排反应及机理.

  酚的物理性质和光谱性质

  酚的化学性质

  酸性及与之相关的反应;Fries重排;芳环上的亲电取代:卤代,硝化,磺化;其它亲电取代:与醛的作用;与CO2的作用;Reimer-Tiemann反应;酚的氧化反应.

  酚的制备方法

  异丙苯氧化法;氯苯水解法;苯磺酸碱熔法.

  醚的反应

  与HX的反应(醚键断裂)及机理;Claisen重排;环氧乙烷的反应.

  醚的合成方法

  Williamson合成法.

  (十)醛和酮

  醛酮的反应①加成反应,亲核加成

  以上反应适用于醛,脂肪族甲基酮和八个碳原子以下的环酮.

  ②碳原子上

  卤仿反应:

  ③氧化和还原

  醛酮的制法

  ①烃类氧化

  ②醇的氧化及去氢

  ③Friedel-Crafts酰化反应

  3.,不饱和醛,酮的反应:

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