脂肪烃知及芳香烃.pptVIP

第五章 芳香烃 Aromatic compounds 1.脂肪烃及芳香烃 Aliphatic and aromatic compounds 芳香性 Aromaticity 2.烷基苯工业来源（ Industrial source of alkylbenzenes ） Coal Petroleum （见书第四节） 3.分类 单环芳烃 多环芳烃 非苯芳烃 第一节 单环芳烃 苯及同系物（ benzene and homolog ） 一.苯的结构 （structure of benzene） 1.开库勒结构式（ Kekule structure） In 1825 M.Faraday In 1834 E.Mitscherlich In 1865 August Kekule August Kekule I was sitting writing at my textbook,but the work did not progress;my thoughts were elsewhere. I turned my chair to the fire,and dozed.Again the atoms were gamboling before my eyes.This time the smaller groups kept modestly in the beckground.My mental eye,rendered more acute by repeated visions of this kind,could now distinguish larger structures of manifold conformations;long rows,sometimes more closely fitted together;all twisting and turning in snake-like motion.But look!What was that?One of the snakes had seized hold of its own tail,and the form whirled mockingly before my eyes.As if by a flash of lightning I woke;……I spent the rest of the night working out the consequences of the hypothesis. Let us learn to dream,gentlemen,and then perhaps we shall learn the truth. August Kekule 苯环结构的诞生是有机化学发展史上的一块里程碑 2.轨道理论Theory of orbit C —SP2 （1） C sp2 hybridized （2） Particularly stable （3）电子离域 Electron Delocalization 3.分子轨道理论Theory of molecular orbit 4.共振（ Resonance structure of benzene ） p-electrons in conjugated dienes and benzene are delocalized 定域电子：被限制在两个原子核区域内运动的电子 离域电子：不局限于两个原子核区域内运动的电子 这种电子的离域作用我们也称之为共轭作用 How to drow resonance contributors Rules for Drawing Resonance Contributors Only electrons move. The nuclei of the atoms never move The only electrons that can move are π electrons and nonbonding electrons The total number of electrons in the molecule does not change, neither do the numbers of paired and unpaired electrons The electrons can be moved in one of the following ways （1） Move πelectrons toward a positive charge （3） Move a nonbonding pair of electrons toward a πbond （4） Move a single