第2章:碳氢化合物课件.ppt
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1、第二周预习思考题n1、有机化合物命名的一般步骤怎样?母体如何选择?各种基团(官能团)的英文词头或词尾的变化规律如何?n2、各种碳氢化合物的稳定性如何?芳香性与共振论是怎么回事?如何画极限共振结构式,并判断它们的能量高低?n3、化合物结构与物理性质的关系如何?n4、非共价弱作用力有哪些?第二章第二章碳氢化合物碳氢化合物Hydrocarbon第二章重点讲解问题n1.碳氢化合物的命名(以烷烃和环烷烃为例)n2.碳氢化合物的稳定性n3.共轭烯烃、芳香性与共振论和分子轨道理论n4.碳氢化合物的物理性质与分子间作用力关系2.1 碳氢化合物的分类与命名n2.1.1 Classification of hyd
2、rocarbonnAlkanes and CycloalkanesnAlkenes(cis and trans)(Z and E)nConjugated dienesnAromatic hydrocarbonsnAlkynes 2.1 碳氢化合物的分类与命名n2.1.2 Representing MoleculesnMolecular formula CH4 Hna Stick figure H C H na Lewis dot structure H na Sawhorse representation HCHHHCHHHH:a solid wedge-in front of the pla
3、nea hatched line-behind the plane2.1 碳氢化合物的分类与命名n2.1.3 通式与不饱和度(环的数目)n Saturated Hydrocarbons:CnH2n+2 n For a formula:CnHm n Degree of unsaturated=(2n+2-m)/2n n If it is a cycloalkane,the degree of unsaturated equals to the number of ring2.1.4 NomenclaturenCommon Name and Systematic Namen CH4 CH3CH3
4、CH3CH2CH3nMethane Ethane Propanen CH3CH2CH2CH3 CH3CHCH3n CH3 nC.N.n-butane isobutanenS.N.Butane 2-methylpropane2.1.4 NomenclaturenCH3CH2CH2CH2CH3 PentanenCH3CHCH2CH3 isopentane,2-methylbutanen CH3n CH3n CH3CCH3 neopentane,2,2-dimethylpropanen CH32.1.4 NomenclaturenCH3CH2CH2CH2CH2CH3 hexanenCH3CHCH2C
5、H2CH3 isohexane,2-methylpentanen CH3 n CH3n CH3CCH2 CH3 neohexane,2,2-dimethylbutanen CH3 2.1.4 NomenclaturenCH3CH2CHCH2CH3 none 3-methylpentane n CH3 nCH3CH-CHCH3 none 2,3-dimethylbutane n CH3 CH3 nAlkyl Group R-(replacing“ane”with“yl”)nprimary,secondary,tertiary,quaternary C,but only primary,secon
6、dary,tertiary H n(see our text)2.1.4 Nomenclature(IUPAC Rules)nSystematic Name(IUPAC Rules)n(IUPAC:International Union of Pure and Applied Chemistry)n1.Determine the number of carbon in the longest continuous carbon chain-This chain is called the parent hydrocarbon.n1 2 3 4 5 6 7 8nCH3CH2CHCH2CH2CH2
7、CH2CH3 3-methyl Octanen CH3 nCH3CHCH2CH2CH3 4-methyl Octanen CH2CH2CH2CH32.1.4 Nomenclature(IUPAC Rules)n2.Number the chain so that the substituent gets the lowest possible number.nCH3CH2CHCH2CHCH2CH2CH3 5-ethyl-3-methyloctanen CH3 CH2CH3 not 4-ethyl-6-methyloctanen because 3 4n CH2CH3nCH3CHCHCH2CH2
8、CHCH3 3-ethyl-2,6-dimethylheptanen CH3 CH3 not 5-ethyl-2,6-dimethylheptanen because 3 52.1.4 Nomenclature(IUPAC Rules)n3.Cite the name of the alkyl substituent before the parent hydrocarbon.-A number and a word are separated by a hyphen;numbers are separated by a comma.di,tri,tetra is used to expres
9、s the number of the same substituentsnCH3CH2CHCH2CHCH3 2,4-dimethylhexanen CH3 CH3 2.1.4 Nomenclature(IUPAC Rules)nAnd list substituents in alphabetical order.-“di,tri,tetra,sec,and tert”are ignored in alphabetizing.“iso,neo,and cyclo”are not ignored in alphabetizing.n 3HC2HC CH3nCH3CH2CCH2CH2CHCHCH
10、2CH2CH3 3,3,6-triethyl-7-methyldecanen 3HC2HC CH2CH3 n CH3nCH3CH2CH2CHCH2CH2CHCH3 5-isopropyl-2-methyloctanen CH(CH3)22.1.4 Nomenclature(IUPAC Rules)n4.If the same substituent number are obtained in both directions,the first cited group received the lower number.n CH3 3-ethyl-5-methylheptanenCH3CH2C
11、HCH2CHCH2CH3 notn CH2CH3 5-ethyl-3-methylheptanen Cl 2-bromo-3-chlorobutanenCH3CHCHCH3 notn Br 3-bromo-2-chlorobutane2.1.4 Nomenclature(IUPAC Rules)n5.If a compound had two or more chains of the same length,the parent hydrocarbon is the chain with the greatest number of substituents.nCH3CH2CHCH2CH2C
12、H3 CH3CH2CHCH2CH2CH3n CHCH3 CHCH3n CH3 CH3 n3-ethyl-2-methylhexane not 3-isopropylhexanen (two substituents)(one substituent)2.1.4 Nomenclature(IUPAC Rules)n6.If there are some complex substituents,we can use the similar method to name the substituents.nCH3CH2CHCH2CH2CH3 CH3CH2CH2CHCH2CH2CH3 n 1 2 1
13、 2 3n CHCH3 CH2CHCH3n CH3 CH3 n 3-isopropylhexane or 4-isobutylheptane orn3-(1-methylethyl)hexane 4-(2-methylpropyl)heptane2.1.4 Nomenclature(IUPAC Rules)n当一个饱和支链无环烃具有相同长度的链可作为当一个饱和支链无环烃具有相同长度的链可作为主链时,则选择的顺序为:主链时,则选择的顺序为:n1)具有侧链数目最多的链)具有侧链数目最多的链n 4-propyl-2,3,5-n trimethylheptanen notn 3-methyl-4-(1
14、,2-n dimethylpropyl)heptaneCH3CH2CHCHCHCH3CH2CH3CHCH3CH3CH2CH32.1.4 Nomenclature(IUPAC Rules)n2)侧链具有最低位次的链)侧链具有最低位次的链n2,5-dimethyl-4-(1-methylpropayl)heptane (not 3,4,5)CH CH2-CHCH3CHCH3CH3CH2CHCH2CH3CH3CH32.1.4 Nomenclature(IUPAC Rules)n3)在较短的侧链中,具有碳原子数目最多的链)在较短的侧链中,具有碳原子数目最多的链n(各侧链数分别为(各侧链数分别为1112
15、88和和111189)n3-ethyl-5,9,11-trimethyl-7,7-di(2,4-dimethylhexyl)tridecaneCCH2CHCH2CHCH2CH3CH2CHCH2CHCH2CH3CH3CH2CHCH2CHCH2CH3CH2CHCH2CHCH2CH3CH3CH3CH3CH3CH2CH3CH3CH3课堂练习:n请给出上述结构的中英文IUPAC命名n1、4-(1-ethylpropyl)-2,5,6,6-tetramethyloctanen2、1-ethyl-2-mehylcyclopentaneCH3CH2C-CHCHCH2CHCH3CH3CHCH2CH3CH3CH3
16、CH2CH3CH3CH2CH3CH31、2、2.1.4 Nomenclature(IUPAC Rules)n7.For cycloalkane:(skeletal structure)n1)In the case of a cycloalkane with an attached alkyl substituent,the ring is the parent hydrcarbon unless the substituent has more carbons than the ring.nA.IsopropylcyclohexanenB.1-cyclobutylpentaneCH2(CH3)
17、2CH2CH2CH2CH2CH3A.B.2.1.4 Nomenclature(IUPAC Rules)n2)If the ring has two different substituents,they are cited in alphabetical order and the number 1 position is given to the first cited substituent.nA.1-ethyl-3-methylcyclopentanenB.1,3-dimethylcyclohexane CH2CH3H3CCH3H3CA.B.2.1.4 Nomenclature(IUPA
18、C Rules)n3)If there are more than two substituents on the ring,give the number 1 position to the substituent that result in a second substituent getting as low a number as possible.nA.1,1,2-trimethylcyclopentane (not 1,2,2;not 1,1,5)nB.4-ethyl-2-methyl-1-propylcyclohexane not 1,3,4,(23);not 5,1,2,(4
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