厦门大学化学化工学院：《有机化学》课程教学资源（授课教案）第四章 卤代烃 Alkyl Halides

第四章卤代 aldes

第四章 卤代烃 Alkyl Halides

Among their many uses, alkyl halides are a employed as industrial solvents, as inhaled r anesthetics in medicine, as refrigerants, E and as pesticides and fumigating agents CIChoCHoCI CH? Br 1.2-Dichloroethane Bromomethane (a solvent (a fumigant F Br ①D F C-H F-C-CI F CI ⑨D Halothane Freon 12 (an inhaled anesthetic)(a refrigerant

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Among their many uses, alkyl halides are employed as industrial solvents, as inhaled anesthetics in medicine, as refrigerants, and as pesticides and fumigating agents. ClCH 2CH 2Cl CH 3Br C C Br Cl H F F F C F Cl F C l 1,2- D i c h l o r o e t h a n e Bromome th a n e (a solvent) (a fu m igant) (an inh aled anesthetic) (a refrigerant) H alothan e Fr e on 1 2

Before discussing the chemistry of alkyl E. halides, it should be pointed out that we wil g be talking primarily about compounds having halogen atoms bonded to saturated sp3-hybridized carbon. Other classes of organohalides, such as aromatic(aryl) and alkenyl(vinylic)halides, also exist, but much of their chemistry is different R一C-X Alkyl halide Aryl halide vinylic halide

Organic Chemistry Organic Chemistry Xiamen Xiamen University University Before discussing the chemistry of alkyl halides, it should be pointed out that we will be talking primarily about compounds having halogen atoms bonded to saturated, sp 3-hybridized carbon. Other classes of organohalides, such as aromatic (aryl) and alkenyl (vinylic) halides, also exist, but much of their chemistry is different. R C X X C C X A l kyl halide A ry l halide V i n ylic halid e

41卤代烃的分类、结构和命名 Classification, Structure, and Nomenclature of Alkyl Halides

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 4.1 卤代烃的分 类 结构和命名 Classification, Structure, and Nomenclature of Alkyl Halides

41,1卤代烃的分类 g按烃基结构分类:饱和卤代烃、不饱和 卤代烃、芳香卤代烃 ·按卤原子个数分类:单卤代烃、二卤代 烃、多卤代烃 按卤素所连碳原子的结构分类:一级卤 代烃、二级卤代烃、三级卤代烃

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 4.1.1卤代烃的分类 „ 按烃基结构分类 饱和卤代烃 不饱和 卤代烃 芳香卤代烃 „ 按卤原子个数分类 单卤代烃 二卤代 烃 多卤代烃 „ 按卤素所连碳原子的结构分类 一级卤 代烃 二级卤代烃 三级卤代烃

412卤代烃的结构 g■键长、键能 c-F C-Cl C-Br C-I 键长139176194 214pI 键能456351293243kJ/mol 已■偶极矩 CH3-F CH3 -CI CH3Br CH3--I |偶极矩182 1.94 1.79 1.64

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 4.1.2卤代烃的结构 „ 键长 键能 C F C Cl C Br C I 139 176 194 214 pm 456 351 293 243 k J / m o l 键长 键能 „ 偶极矩 CH 3 F CH 3 Cl CH 3 Br CH 3 I 偶极矩 1 . 8 2 1 . 9 4 1 . 7 9 1 . 6 4

413卤代烃的命名 -卤代烃不作为一类母体化合物 ■卤原子在命名时始终作为取代基 n卤原子的英文词头: fluoro-, chloro- bromo- iodo-

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 4.1.3卤代烃的命名 „ 卤代烃不作为一类母体化合物 „ 卤原子在命名时始终作为取代基 „ 卤原子的英文词头 fluoro-, chloro-, bromo-, iodo-

42卤代烃的物理性质 Physical Properties of Alkyl Halides

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 4.2 卤代烃的物理性质 Physical Properties of Alkyl Halides

e沸点:分子的极性越大,偶极一偶 极相互作用也大,沸点升高 ■溶解度:卤代烃不溶于水 ■密度:只有一氯代烃、一氟代烃比 水轻

Organic Chemistry Organic Chemistry Xiamen Xiamen University University „ 沸点 分子的极性越大 偶极 — 偶 极相互作用也大 沸点升高 „ 溶解度 卤代烃不溶于水 „ 密度 只有一氯代烃 一氟代烃比 水轻

43卤代烃的化学性质 Chemical properties of Alkyl Halides

Organic Chemistry Organic Chemistry Xiamen Xiamen University University 4.3 卤代烃的化学性质 Chemical properties of Alkyl Halides