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1、Chapter 4Alcohols and Alkyl Halides,(1) alcohol + hydrogen halide ROH + HX RX + H2O (2) alkane + halogen RH + X2 RX + HX Both are substitution reactions,Overview of Chapter,This chapter introduces chemical reactions and their mechanisms by focusing on two reactionsthat yield alkyl halides.,4.1IUPAC
2、Nomenclatureof Alkyl Halides,The two that are most widely used are:functional class nomenclaturesubstitutive nomenclature Both types can be applied to alcohols andalkyl halides.,IUPAC Nomenclature,There are several kinds of IUPAC nomenclature.,Name the alkyl group and the halogen asseparate words (a
3、lkyl + halide),Functional Class Nomenclature of Alkyl Halides,CH3F,CH3CH2CH2CH2CH2Cl,Name the alkyl group and the halogen asseparate words (alkyl + halide),Functional Class Nomenclature of Alkyl Halides,CH3F,CH3CH2CH2CH2CH2Cl,Methyl fluoride,Pentyl chloride,1-Ethylhexyl bromide,Cyclohexyl iodide,Nam
4、e as halo-substituted alkanes. Number the longest chain containing thehalogen in the direction that gives the lowestnumber to the substituted carbon.,Substitutive Nomenclature of Alkyl Halides,CH3CH2CH2CH2CH2F,Name as halo-substituted alkanes. Number the longest chain containing thehalogen in the di
5、rection that gives the lowestnumber to the substituted carbon.,Substitutive Nomenclature of Alkyl Halides,CH3CH2CH2CH2CH2F,1-Fluoropentane,3-Iodopentane,2-Bromopentane,Substitutive Nomenclature of Alkyl Halides,Halogen and alkyl groupsare of equal rank when it comes to numberingthe chain. Number the
6、 chain in thedirection that gives the lowest number to thegroup (halogen or alkyl)that appears first.,Substitutive Nomenclature of Alkyl Halides,5-Chloro-2-methylheptane,2-Chloro-5-methylheptane,4.2IUPAC Nomenclatureof Alcohols,Name the alkyl group and add alcohol as aseparate word.,Functional Class
7、 Nomenclature of Alcohols,CH3CH2OH,Name the alkyl group and add alcohol as aseparate word.,Functional Class Nomenclature of Alcohols,CH3CH2OH,Ethyl alcohol,1-Methylpentyl alcohol,1,1-Dimethylbutylalcohol,Name as alkanols. Replace -e ending of alkanename by -ol. Number chain in direction that gives l
8、owest numberto the carbon that bears the OH group.,Substitutive Nomenclature of Alcohols,CH3CH2OH,Name as alkanols. Replace -e ending of alkanename by -ol. Number chain in direction that gives lowest numberto the carbon that bears the OH group.,Substitutive Nomenclature of Alcohols,CH3CH2OH,Ethanol,
9、2-Hexanol,2-Methyl-2-pentanol,Substitutive Nomenclature of Alcohols,Hydroxyl groups outrank alkyl groups when it comes to numberingthe chain. Number the chain in thedirection that gives the lowest number to thecarbon that bears theOH group,Substitutive Nomenclature of Alcohols,6-Methyl-3-heptanol,5-
10、Methyl-2-heptanol,4.3Classes of Alcoholsand Alkyl Halides,Alcohols and alkyl halides are classified asprimarysecondarytertiaryaccording to their degree of substitution. Degree of substitution is determined by countingthe number of carbon atoms directly attached tothe carbon that bears the halogen or hydroxyl group.,Classification,CH3CH2CH2CH2CH2F,primary alkyl halide,secondary alkyl halide,Classification,tertiary alcohol,H,OH,secondary alcohol,
