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Chapter 7 alkyl halide Ionic Reactions---Nucleophilic substitution and.ppt
Chapter 7 alkyl halides Alkyl halide: a compound containing a halogen atom covalently bonded to an sp3 hybridized carbon atom given the symbol RX Ionic Reactions---Nucleophilic substitution and elimination reactions of alkylhalides Because halogen atoms are more electronegative than carbon, the carbon-halogen bond of alkyl halides is polarized; the carbon atom bears a partial positive charge, the halogen atom a partial negative charge. Table 6.1 Carbon-halogen bond lengths Vinyl halides (卤代乙烯） or phenyl halides （卤代苯基） 6.2 Physical properties of organic halides Very low solubilities in water They are miscible with each other and with other relatively nonpolar solvents CH2Cl, CHCl3 and CCl4 are often used as solvents for nonpolar CHCl3 and CCl4 have a cumulative toxicity and are carcinogenic. Polyfluoroalkanes have low boiling points, (Hexafluoroethane boils at –79o) 6.3 Reaction Mechanisms Mechanism of the reaction—The events that are postulated to take place at the molecular level as reactants become products If the reaction takes place in more than one step, then what are these steps, and what kinds of intermediates intervene between reactants and products? 6.3A Homolysis and heterolysis of covalent bonds (共价键的均裂和异裂） 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) Heterolysis of a bond can lead either to a trivalent carbon cation or carbon anion 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） Nucleophilic substitution re
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