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,单击此处编辑母版文本样式,第二级,第三级,第四级,第五级,*,单击此处编辑母版标题样式,Company,Logo,Nomenclature of Organic Compounds,有机化合物的命名,Company,Logo,Brief Introduction,Hydrocarbons,All organic compounds can be regarded as based on the structures of hydrocarbons.,Saturated hydrocarbons,contain only single covalent bonds; they may consist of straight or branched carbon chains (,alkanes,) or rings (,cycloalkanes,). All hydrocarbons with more than three carbon atoms exhibit structural isomerism. Groups containing one less hydrogen atom than an alkane are called,alkyl groups,.,Unsaturated hydrocarbons,are those containing double bonds (,alkenes,) or triple bonds (,alkynes,).,Company,Logo,Rotation of two carbon atoms joined by a double bond is inhibited by the,bond, and these two carbon atoms are similarly unable to rotate. In both cases,cis-trans,isomerism is therefore possible. A carbon-carbon double bond creates a planar region in a molecule. The double bonds that alternate with single bonds are named as,conjugated double bonds(,共轭双键,).,Company,Logo,Aromatic hydrocarbons(,芳烃,),are unsaturated compounds with planar ring systems stabilized by delocalized,bonding, as in benzene. Hydrocarbons that do not contain aromatic rings are termed,aliphatic(,脂肪族,) hydrocarbons,. The preferred system of nomenclature for organic compounds is that formulated by the International Union of Pure and Applied Chemistry, IUPAC.,Company,Logo,Isomerism,Pairs of molecules with the same molecular formula that rotate,plane-polarized,light in opposite directions are called,optical isomers(,旋光异构,),or,enantiomers(,对映异构,),. They are mirror images of one another and are usually very similar in their properties, and so are difficult to separate.,Company,Logo,Optical isomers may arise when four different groups are bonded to one carbon atom, producing an,asymmetric,molecule. The property of having optical isomers is called,chirality(,手性,),. A mixture of equal parts of the,levorotatory(,左旋,),and,dextrorotatory(,右旋,),isomers of a substance a,racemic(,外消旋,),mixture, causes no net rotation of polarized light(,偏振光,).,Company,Logo,Reactivity,The reactivity of saturated hydrocarbons is generally low, although hydrogen atoms are readily replaced by,halogen,atoms (,halogenation,). Double bonds or polar bonds provide sites where reaction is more likely to occur. Unsaturated hydrocarbons readily undergo,addition reactions,; aromatic compounds tend to undergo,substitution reaction,.,Company,Logo,Some Introductory Concepts,A,functional group,is a chemically reactive atom or group of atoms that imparts characteristic properties to the family of organic compounds containing it. The site of reaction in an organic molecule is often a functional group, a multiple covalent bond, or a polar single bond. An electron-poor atom or group that will bond with an atom that has an available electron pair is called an,electrophile,. An electron-rich atom or group that will bond with an electron-deficient atom is called a,nucleophile,.,Company,Logo,Nomenclature of Hydrocarbons:,（烃类命名法）,Number Prefix,（数字前缀）：,总碳数,10,时,甲,: meth-,壬,: nona-,乙,: eth-,癸,: deca-,丙,: prop-,半,: hemi-, semi-,丁,: buta-,单,: mono-,戊,: penta-,双,两,: di-,己,: hexa- bi-, bis-,庚,: hepta-,辛,: octa-,Company,Logo,总碳数,10,时：,一,: hen(i)-;,二,: do-;,三,: tri(a)-;,四,: tetra-,10. deca- 20: eicosa- 30: triaconta-,11:,un,deca,hen,deca- 21:,hen,eicosa- 31:,hen,triaconta-,12:,do,deca- 22:,do,cosa-,40: tetraconta-,13: trideca- 23: tricosa-,50: pentaconta-,14: tetradeca- 24: tetracosa-,60: hexaconta-,15:pentadeca- 25: pentacosa-,70: heptaconta-,16: hexadeca- 26: hexacosa-,80: octaconta-,17: heptadeca- 27: heptacosa-,90: enneaconta-,18: octadeca- 28: octacosa-,19: nonadeca- 29: nonacosa-,Company,Logo,表示取代基相对位置的字头：,iso-,异；,cis-,顺；,trans-,反,neo-,新；,primary,伯,o-,（,ortho-,）邻；,secondary,仲,sec-,m-,（,meta-,）间；,tertiary,叔,tert-,p-,（,para-,）对；,quaternary,季,Company,Logo,烷烃（,alkane-,paraffin hydrocarbons,石蜡烃,/,烷属烃,/,链烷烃,C,n,H,2n+2,）命名,数字头,+ -ane,（以,a,结尾的数字头直接加,-ne,）,甲烷,: methane;,癸烷,: decane;,庚烷,: heptane;,十三烷,: tridecane,十四烷,: tetradecane,十五烷,: pentadecane,二十烷,: (e)icosane,二十一烷,: heneicosane,二十二烷,: docosane,三十烷,: triacontane,三十一烷,: hentriacontane,四十烷,: tetracontane,五十烷,: pentacontane,六十烷,: hexacontane,七十烷,: heptacontane,八十烷,: octacontane,九十烷,: nonacontane,1,）,Aliphatic Hydrocarbons,（,Fatty Hydrocarbons,，脂肪烃）,例,:,Company,Logo,Company,Logo,C,n,H,2n+1,radicals (alkyls/,hydrocarbyl,),烃基的命名：,将烃类名称的词尾,“,ane” “yl”,CH,4,methane;,CH,3,methyl,甲基,propane propyl butane butyl;,pentane pentyl;,hexane hexyl,heptane heptyl;,octane octyl,nonane nonyl;,decane decyl,癸基,Company,Logo,Common nomenclature of alkanes,First, described as above.,Second, there are some rules:,n-: normal(,正,), implies a straight-chain or,unbranched alkane,i-: iso-(,异,), implies a branched alkane with the,second carbon in the end of chain linking,with a methyl.,neo-: (,新,), implies a branched alkane with the,second carbon at the end of chain linking,with two methyls.,Company,Logo,E.G.,C-C-C-C-C n-pentane,正戊烷,C-C-C-C isopentane,异戊烷,C-C-C neopentane,新戊烷,C,C,C,Company,Logo,支链烃类（,hydrocarbon with branched chains,）的命名：,i).,以最长的碳链为主链，从一端向另一端编号，使侧链具有最低编号。如有几个侧链，按侧链取代基字头的英文,字母顺序,排列。,例：,：,5-,甲基,-4-,丙基壬烷,5-methyl-4-propylnonane,Company,Logo,4-,甲基,-6-,乙基癸烷,6-ethyl-4-methyldecane,2,7-,二甲基,-3-,乙基,-4-,丙基辛烷,3-ethyl-2,7-dimethyl-4-propyloctane,Company,Logo,Systematic nomenclature of alkanes,Step 1: Choose the longest continuous carbon chain with the greatest number of substituents as present body.,C-C-C-C-C-C,C-C,C,1,2,3,4,5,6,C-C-C-C-C-C,C-C,C,4,1,2,3,5,6,4-isopropyl hexane,4-,异丙基己烷,3-ethyl-2-methyl hexane,2-,甲基,-3-,乙基己烷,False,True,Company,Logo,Step 2: Give the substituents the lowest position number.,C-C-C-C-C-C,C-C,C,4,1,2,3,5,6,3-ethyl-2-methyl hexane,2-,甲基,-3-,乙基己烷,True,C-C-C-C-C-C,C-C,C,3,6,5,4,2,1,4-ethyl-5-methyl hexane,5-,甲基,-4-,乙基己烷,False,Company,Logo,Step 3: Give the first listed substituent a possible lower position number, and the sum of the position numbers for all substituents should be as low as possible.,C,C-C-C-C-C-C-C,C-C,C,C,C,1,7,C,C-C-C-C-C-C-C,C-C,C,C,C,1,7,Number: 2,4,6,Number: 2,4,5,4-Isobutyl-2,5-dimethyl heptane,2,5-,二甲基,-4-,异丁基庚烷,2,6-dimethyl-4-secbutyl heptane,2,6-,二甲基,-4-,仲丁基庚烷,Company,Logo,4-ethyl-2,5-dimethyl,heptane,2,2-dimethyl,propane,5-isopropyl-4-methyl,octane,4-methyl-5-(2-methylethyl),octane,Company,Logo,Question:,What is the difference between Chinese Nomenclature System and English Nomenclature System?,Company,Logo,Answer:,(i),含有支链的化合物，支链名称的先后，,国际上按其英文名称的第一个字母的先,后而排列,(,即,A,、,B,、,C,次序排列,),。我国则,按“简单在前，复杂在后”的原则排列，,主要是看分子量大小，如先,-CH,3,，后,-Cl,。,Company,Logo,(ii),在命名中使用基团的倍数词头时,(di-, tri-,tetra-, penta-, hexa-, hepta-, octa-, nona-),，如基,团简单，命名时可不把倍数词头作为排列,先后来考虑，如,ethyl,时列在,dimethyl,之前。,当倍数词头与复杂基团合并作为一个完整,基团时，则以倍数词头的第一个字母为依,据，如,dimethyl-pentyl,就应以,d,作为第一个字,母而列在,ethyl,之前。,Company,Logo,Types of Carbon Atom:,伯,primary (1,) C,bonded with only one C -CH,3,仲,secondary (2,) C -CH,2,-,叔,tertiary (3,) C -CH-,季,quarternary (4,) C -C-,-C-C-C-C,n-Butyl (,正,),丁基,-C-C-C,i-Butyl (,异,),丁基,C,-C-C-C,s-Butyl (,仲,),丁基,C,-C-C,t-Bu (,叔,),丁基,C,C,Company,Logo,Besides the iso-, neo-, tert-, there is another means to name the complex groups.,E.G.,-C-C-C s-Butyl (,仲,),丁基,C,It can be also named as “1-methyl propyl”.,Company,Logo,烯烃（,alkene,）命名：,数字头,+ -ene,（以,a,结尾的数字头去,a,加,-ene .,）,多烯的命名,:,二烯类：数字头,+ -diene,三烯类：数字头,+ -triene,例,:,乙烯,: ethene,丁烯,: butene,丁二烯,:,buta,diene,丁三烯,:,buta,triene,烃基类：,乙烯基,: ethenyl,丁烯基,: butenyl,乙炔基,: ethynyl,苯基：,phenyl,苄基：,benzyl,Company,Logo,炔烃,(alkyne ),命名：数字头,+ -yne,（,-ine,）,（以,a,结尾的数字头去,a,加,-yne .,）,多炔的命名,:,二炔类：数字头,+ -diyne,三炔类：数字头,+ -triyne,例,:,乙炔,: ethyne/acetylene(,俗名,),丁炔,: butyne;,己二炔,: hexadiyne / hexadiine,Company,Logo,Nomenclature for unsaturated hydrocarbons,a.,Alkenes (olefins,烯烃,) C,n,H,2n,and alkynes (acetylenes,炔烃,) C,n,H,2n-2,Alkenes are named similarly to alkanes, with the following modification:,The longest continuous chain that includes both carbons of the double bond provides the root.,Company,Logo,The suffix used for an alkene is -ene. Names for compounds with more than one double bond use the suffixes diene, -triene, and so on.,The root is numbered from the end that gives the lower number to the first carbon of the double bond. The number of this first carbon is used in the name to designate the position of the double bond.,Company,Logo,Similarly, the individual alkynes are named by dropping the ane and adding yne, a diyne, a triyne, and so on. In either case, the position of the multiple bond is indicated by numbering from the end of the chain, starting at the end that will assign the lower number to the first carbon atom of nomenclature bond. e.g., 1,3-pentadiyne.,Company,Logo,In the common system of nomenclature,习惯命名法, the,ane,ending of the saturated hydrocarbon name is replaced by,ylene,for the olefins relative to the number of carbon is within,four,. Compounds containing triple bonds are sometimes named as substituted acet,ylene,s. (Because of the triple bond between the carbon atoms in acetylene, each carbon can have only one group attached to it.),Company,Logo,Common Names for Some Compounds and Groups Containing Multiple Bonds,Compound or Group Common Names,CH,2,=CH,2,ethylene,CH,2,=CHCH,3,propylene,CH,2,=CHCH,2,CH,3,butylene,CH,3,CH=CHCH,3,-butylene,CH,2,=CCH,3,isobutylene,CH,2,=C=CH,2,丙二烯,allene,CH,3,Company,Logo,CH,3,CH,2,=C-,CH,2,=CH- vinyl (ethenyl) group,-CH=CHCH,3,丙烯基,(1-) propenyl group,CH,2,=CHCH,2,-,烯丙基,allyl (2-propenyl) group,CH,3,CH=CHCH,2,- crotyl group,CH=C- ethynyl,-C=CCH3,丙炔基,1-propynyl,CH=CCH,2,-,炔丙基,propargyl (2-propynyl),CH,2,=CH-C=CH vinylacetylene 1-buten-3-yne,异丙烯基,Isopropenyl,Company,Logo,不饱和烃中应使不饱和键的编号最小,如：,3-,甲基,-1-,丁烯,3-methyl-1-butene,或,3-methylbut-1-ene,Simple alkenes and alkynes,Company,Logo,：,1,3-,丁二烯,butadiene,或,1,3-butadiene,或,buta-1,3- diene,2-,甲基,-1,3 -,丁二烯,2-methyl-1,3 butadiene/ 2-methylbuta-1,3-diene,Company,Logo,Company,Logo,C-C-C=C-C-C,C,Ph,trans-5,5-dimethyl-2-hexene,C-C=C-C-C-C,C,C,H,H,2-methyl-1-phenyl-3-hexyne,Company,Logo,Cycloalkenes,1,5-cyclooctadiene,3,5-dimethyl cyclohexene,-1-,Company,Logo,*,同时含有双键和三键时，用,-enyne,结尾。,如：,3-,戊烯,-1-,炔,3-penten-1-yne/pent-3-en-1-yne,1-,己烯,-4-,炔,1-hexen-4-yne/ hex-1-en-4-yne,Company,Logo,烯写在炔前,C-C-C-C=C-C-C-C,C=C,C=C,3,4-dipropyl-1,3-hexadien-5-yne,当双键和三键位次相同时，给双键最低位次,Company,Logo,CH,2,-CH,2,CH,2,-CH,H,2,C,CH,2, C=C-CH,2,CH,1,2,4,3,5,6,7,8,9,10,1-cyclodecen-4-yne,cyclodec-1-en-4-yne,When there is an equal choice in numbering, double bonds are given lower numbers than triple bonds.,Company,Logo,HC=C-CH=CH-CH=CHCH,3,1,2,4,3,5,6,7,3,5-heptadien-1-yne,hepta-3,5-dien-1-yne,Numbers as low as possible are given to the double and triple bonds even though this results in the triple bond having the lower number. Note the location in the name of 3 and 5, which refer to diene, and 1, to yne.,Company,Logo,CH,2,=CH-CH-CH=CH-CH=CH,2,C=CH,1,2,4,3,5,6,7,5-ethenyl-1,3-heptadien-6-yne,注意：主链是包含双键或三键的最长碳链,Company,Logo,脂环烃,Cyclo,alkanes (alicyclic hydrocarbons or cycloparaffin,脂环族烃,/,环烷烃,) C,n,H,2n,命名,:,烃类名称前,+ cyclo-,例,:,环己烷,: cyclohexane;,环己二烯,: cyclohexadiene,环辛四烯,: cyclooctatetraene,Company,Logo,环烃有取代基时，将环作为母体，对取代基进行编号。如取代基较复杂，取代基内部可单独编号,如：,：,1-,甲基,-2-,（,3-,甲基丁基） 环己烷,1-methyl-2-(3-methylbutyl) cyclohexane,Company,Logo,2,）芳香烃（,Aromatic Hydrocarbons,）,:,以苯（,benzene,）作为母体，其它作为取代基。,(1-,甲基乙基,),苯 又名：异丙基苯,(1-methyl ethyl) benzene /isopropylbenzene,1,3,5-,三甲苯,1,3,5-trimethylbenzene,如：,Company,Logo,Company,Logo,o,-xylene,m,-xylene,p,-xylene,o,，,m,，,p,-dimethylbenzene,benzene,toluene,methylbenzene,Company,Logo,nitrobenzene,ethylbenzene,chlorobenzene,苯乙烯,styrene,phenylethene,N,O,2,Company,Logo,aniline,/benzenamine,苯胺,Cyanobenzene,苯甲腈,phenol,苯酚,Company,Logo,对硝基氯苯,p,-nitrochlorobenzene,间羟基苯甲酸,m,-hydroxybenzoic acid,Company,Logo,2-,氨基,-5-,羟基苯甲醛,2-amino-5-hydroxybenzaldehyde,3-,硝基,-2-,氯苯磺酸,2-chloro-3-nitrobenzenesulfonic acid,Company,Logo,2.,其它有机物的命名,:,*,首先选择主要的官能团。在,IUPAC,规定的官能团顺序中，位置在前的官能团优先，可作为主要的官能团，其余的作为取代基。,IUPAC,官能团顺序：,1,）游离基；,2,）阳离子化合物；,3,）中性配位化合物；,4,）阴离子化合物；,5,）酸；,6,）酰卤；,7,）酰胺；,8,）腈；,Company,Logo,9,）醛（硫醛）；,10,）酮（硫酮）；,11,）醇、酚（硫醇、硫酚）；,12,）过氧化物；,13,）胺；,14,）亚胺；,15,）,26,）为元素有机化合物，顺序为：,N,P,As,Sb,Bi,B,Si, Ge,Sn,Pb,O,S,；,27,）碳环化合物及无环烃类；,28,）卤化物中的卤素,Company,Logo,系统命名是以骨架名称加上主要官能团的词尾，再在前面加上取代基的字头和定位号。,5-,羟基,-2-,戊酮,5-hydroxy-2-pentanone,如：,Company,Logo,1),卤化物（,Halogenide,，,Halide,）的命名：在相应的烃的名称前,+,“,卤代,”,fluoro-,氟代（,fluorine,氟）,chloro-,氯代（,chlorine,氯）,bromo-,溴代（,bromine,溴）,iodo-,碘代（,iodine,碘）,例,2-,氯,-2-,甲基丙烷,2-chloro-2-methyl propane,Company,Logo,一些俗名：氯仿,(,哥罗芳,CHCl,3,),，,chloroform,；溴仿，,bromoform,；氟里昂,CFC,，,Freon,CCl,2,F,2,(CFC-12),溴甲基苯,bromomethylbenzene,1,2-,二溴乙烷，,1,2-dibromoethane,Company,Logo,2,）醇、酚、醚（,Alcohol,，,Phenol,，,Ether,）的命名：,*,醇、酚：在相应的烃的名称后，去,“,-e,”,加,“,-ol,”,。如果是二醇或三醇，则须加,“,-diol,”,或,“,-triol,”,（在很多情况下不去,“,-e,”,）。,例：,2-,甲基,-2-,丙醇,2-methyl-2-propanol,（,2-methyl propan-2-ol,）,Company,Logo,例：,2-,乙基,-2-,丁烯,-1-,醇,2-ethyl-2-buten-1-ol,（,2-ethyl-but-2-en-1-ol,）,1,2-,乙二醇，,1,2-ethanediol,（,ethane-1,2-diol,）,1,2,3-,丙三醇，,1,2,3-propanetriol,（俗称甘油，,glycerin,）,Company,Logo,*,当羟基位于侧链时，侧链上的羟基可作取代基处理。取代基形式的羟基用,“,hydroxy-,”,表示。,2-,羟基,-1-,环己烷羧酸,2-hydroxy-1-cyclohexane,carboxylic acid,2-,羟甲基,-1,4-,丁二醇,2-hydroxymethyl-1,4-butanediol,1,4-,苯二酚,1,4-benzenediol,1,2,4,-,苯三酚,1,2,4-benzenetriol,例：,Company,Logo,*,醚的命名：将较简单的烷类与氧原子一起作为取代基命名。烷氧基名称：烷基字头,+,“,-oxy,”,。,乙基乙烯基醚,ethoxy ethene,甲基苯基醚,methoxy benzene,环己基苯基醚,cyclohex,yl,oxy benzene,例：,低于五个碳的烷氧基的英文名称将烷基词尾“,yl”,省略,Company,Logo,*,环醚：以烃基为母体，在前面加上,“,epoxy-,”,，并且标出与氧原子相连的碳原,子的编号。,1,2-,环氧丙烷，,1,2-epoxypropane,1,3-,环氧丙烷，,1,3-epoxypropane,1,4-,环氧丁烷,1,4-epoxybutane,； 俗名：四氢呋喃,tetrahydrofuran(THF),Company,Logo,3,）羧酸（,Carboxylic Acid,）的命名：,命名法,1,：将同样碳数的烃的名称后去,-e,加,“,-oic acid,”,。编号从,-COOH,上的碳原子开始。（多用于链状的酸）,dioic acid trioic acid,命名法,2,：在羧基以外的,烃的名称,后加上,“,carboxylic acid,”,。编号从与,-COOH,相邻的碳原子开始。（多用于羧基直接连在环上的酸）,dicarboxylic acid tricarboxylic acid,特例：一些酸保留俗名。如：,醋酸，,acetic acid,；苯甲酸，,benzoic acid,；,甲酸（蚁酸）,formic acid,Company,Logo,2-,甲基丁酸，,2-methyl butanoic acid,3-,戊烯酸，,3-pentenoic acid,2-,甲基,- 4-,乙基戊二酸，,2-ethyl-4-methylpentanedioic acid,Company,Logo,十八酸，,octadecanoic acid,乙二酸，,ethanedioic acid,草酸，,oxalic acid,十二酸，,dodecanoic acid,Company,Logo,环己烷羧酸，,cyclohexane carboxylic acid,1,2-,苯二甲酸，,1,2-benzenedicarboxylic acid,Company,Logo,4,）,醛、酮（,Aldehyde,，,Ketone,）的命名：,*,醛：将同样碳数的烃的名称后去,-e,加,-al,。,例：,HCHO,甲醛，,methanal;,2-,甲基丙醛,2-methylpropanal,3-,甲基,-2-,乙基戊醛,2-ethyl-3-methylpentanal,Company,Logo,*,酮：将同样碳数的烃的名称后去,-e,加,-one,。,2-,戊酮，,2-pentanone,甲基丙基酮,methyl propyl ketone,例,丙酮,propanone,二甲基酮,dimethyl ketone,环己酮,cyclohexanone,Company,Logo,5,）酯类（,Ester,）的命名：,*,命名法：醇的部分作为取代基，酸的部分去,“,-ic acid,”,加,“,-ate,”,。,乙酸甲酯，,methyl ethanoate,methyl acetate,丙酸乙酯，,ethyl propanoate,苯甲酸丁酯，,butyl benzoate,Company,Logo,6,）胺类（,Amine,）的命名：,乙胺,ethylamine,ethanamine,普通命名法：相应的烃基名称后加“,amine”,系统命名法：选含氮最长的碳链为母体，氮上其它烃作为取代基，并用,N,定位，用,amine,代替词尾“,e”,diamine triamine,甲胺,methylaminemethanamine,Company,Logo,二甲胺,dimethylamine,N-methylmethanamine,三甲胺,trimethylamine,N,，,N-dimethylmethanamine,Company,Logo,1,2-,乙二胺,1,，,2-ethanediamine,N,N-,二甲基丁胺,N,N-dimethylbutanamine,Company,Logo,苯胺,aniline,benzenamine,N,4-,二甲基,-N-,乙基苯胺,N-ethyl-N,4-dimethylbenzenamine,Company,Logo,做为母体时，要把,CN,中的碳原子计算在内，应从,CN,开始编号，烃类名称后加,nitrile,作为取代基时写成氰基，,cyano-,7,）腈类（,Nitriles,）的命名：,3-,甲基戊腈,3-methylpentanenitrile,3-,氰基丁酸,3-cyanobutanoic acid,Company,Logo,普通命名法：把,“,oic acid,”,或,“,ic acid,”,换为,“,onitrile,”,乙腈,acetonitrile,苯甲腈,benzonitrile,Company,Logo,呋喃,噻吩,吡咯,吡啶,N,H,Porphyrin,卟啉,Company,Logo,Company,Logo,O,CH,3,H,3,C,O,H,O,H,O,H,OHC,Company,Logo,cyclohexan,amine,N,H,2,N,H,2,2-methylpropan-1-,
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