6. 3A Homolysis and heterolysis of covalent bonds(共价键的均裂和异 裂) Covent bond may break in three possible ways A·+B·Homs(均裂) A:: : B A: -+B Heteroly (异裂) a+: B
6.3A Homolysis and heterolysis of covalent bonds (共价键的均裂和异 裂） A : B A + B A: + B A + + :B - . . - + Homolysis（均 裂 ） Heterolysis （ 异 裂 ） Covent bond may break in three possible ways:
6.3b Reactive intermediates in organic chemistry Organic reactions that take place in more than one step involve the formation of an intermediate----one that results from either homolysis or heterolysis of a bond Homolysis of a bond to carbon leads to an intermediate known as a carbon radical (free adical) homolysis C Z C t Z 均裂 Carbon radical or free radical
6.3B Reactive intermediates in organic chemistry Organic reactions that take place in more than one step involve the formation of an intermediate----one that results from either homolysis or heterolysis of a bond. Homolysis of a bond to carbon leads to an intermediate known as a carbon radical (free radical) C : Z homolysis C . + Z . 均 裂 Carbon radical or free radical
Heterolysis of a bond can lead either to a trivalent carbon cation or carbon anion tZ Carbocation heterolysis (or carbenium ion) C Z (碳阳离子) 异裂 C Carbanion (碳阴离子 Carbanions are usually strong bases and strong nucleophiles Nucleophiles are lewis bases ley are electron-pair donors. Carbon radicals, carbocations, and carbonions are usually highly reactive species
Heterolysis of a bond can lead either to a trivalent carbon cation or carbon anion C : Z heterolysis C + Z 异 裂 Carbocation (or carbenium ion) （ 碳 阳 离 子 ） C + Z Carbanion （ 碳 阴 离 子 ） + : - : - + Carbanions are usually strong bases and strong nucleophiles. Nucleophiles are lewis bases they are electron-pair donors. Carbon radicals, carbocations, and carbonions are usually highly reactive species
6.3 c onic reactions(离子反应) and radical reactions(自由基反应 or游离基反应) In ionic reactions the bonds of the reacting molecules undergo heterolysis In radical reactions, they undergo homolysis(in detail in chapter 7) In this chapter we concern ourselves only with ionic reactions
6.3C Ionic reactions (离子反应） and radical reactions（自由基反应 or 游离基反应） • In ionic reactions the bonds of the reacting molecules undergo heterolysis; • In radical reactions, they undergo homolysis (in detail in chapter 7) • In this chapter we concern ourselves only with ionic reactions
6.4 Nucleophilic substitution reactions(亲核 取代反应) u R——X R—Nu+x Nucleophile Alkyl halide Product Halide ion 亲核试剂 Substrate底物) Ho CH CH3OH CI CH3O CH3-Br CH3OCH3 Br r+CH3CH2CH2-—c CH3CH, I Cl
6.4 Nucleophilic substitution reactions (亲核 取代反应） Nu : - + R X R Nu + : - X Nucleophile 亲 核 试 剂 Alkyl halide (Substrate 底物) Product Halide ion HO - + CH3 Cl CH3 OH + Cl - CH3 O - + CH3 Br CH3 OCH3 + Br - I - + CH3 CH2 CH2 Cl CH3 CH2 CH2 I + Cl -