专业英语-有机物命名

1、Nomenclature of organic compounds By Xingwang Zhou Hydrocarbons are composed entirely of carbon and hydrogen atoms bonded to each other by covalent bonds. Several series of hydrocarbons are known. These include the , , , and . It is necessary to learn the names of the first 10 members of the alkane

2、series as these names are used, with , for corresponding compounds belonging to . Alkanes are acyclic hydrocarbons of general formula CnH2n+2 The carbon atoms are arranged in chains that are either or . Rule-1 Saturated unbranched acyclic hydrocarbons pThe first four saturated unbranched acyclic hyd

3、rocarbons are called methane, ethane, propane and butane. 饱和直链非环状烃 pNames of the higher members of this series consist of a , followed by ” with elision of terminal “ ” from the numerical term. alkane= “Numerical term” + ane 碳数碳数中文中文英文英文 10癸烷癸烷decane 1甲烷甲烷methane11十一烷十一烷undecane 2乙烷乙烷ethane12十二烷十二烷d

4、odecane 3丙烷丙烷propane13十三烷十三烷tridecane 4丁烷丁烷butane14十四烷十四烷tetradecane 5戊烷戊烷pentane15十五烷十五烷pentadecane 6己烷己烷hexane16十六烷十六烷hexadecane 7庚烷庚烷heptane17十七烷十七烷heptadecane 8辛烷辛烷octane18十八烷十八烷octadecane 9壬烷壬烷nonane19十九烷十九烷nonadecane Rule alkyls= pAlkyl radicals have the general formula CnH2n+1. pThe name of t

5、he radical is formed from the name of the corresponding alkane by simply dropping “” and substituting a “” ending. pAs a class, these radicals are called . 烷基：将烷烃结尾的烷基：将烷烃结尾的“ane”换为换为“yl” “alkane+yl” 常见基团 基团中文名基团英文名构造式 甲基甲基methyl-CH3 乙基乙基ethyl-CH2CH3 丙基丙基propyl-CH2CH2CH3 丁基丁基butyl-CH2(CH2)2CH3 戊基戊基p

6、entyl-CH2(CH2)3CH3 IUPAC rules for naming alkanes the longest continuous chain of carbon atoms as the , and consider all alkyl attached to it as that have replaced hydrogen atoms of the parent hydrocarbon. the carbon atoms in the parent carbon chain from that gives the to the branch chains each and

7、designate its position on the parent carbon chain by a number. IUPAC rules for naming alkanes IV.When the same alkyl group branch chain occurs , indicate this by a prefix, , written in front of the alkyl group name. The numbers indicating the positions of these alkyl groups are placed in front of th

8、e name. V.If two or more side chains of different nature are present, they are cited in alphabetical order. (e.g., 3- thyl-4-ethyloctane). Training n2-甲基丁烷 n2-甲基-3-乙基庚烷 2-methylbutane 3-ethylheptane2,4,8-trimethylnonane 3- thyl-2-ethylheptane 2,3-dimethylpentane CH3 CH3CH3 The following names are re

9、tained for unsubstituted hydrocarbons only: 下列未取代的碳氢化合物的名称保留 p正n- p异iso- p新neo- CH3 CH2 CH CH3 CH3 CH3 C CH3 CH3 CH3 n-pentane iso-pentane neo-pentane isobutane、isohexane 2-methylbutane 2,2-dimethylpropane 32223 CHCHCHCHCH 基团中文名基团英文名构造式 异丙基异丙基isopropyl-CH（CH3)2 异丁基异丁基isobutyl-CH2CH（CH3)2 叔丁基叔丁基Tert-

10、butyl-CH2CH2CH(CH3)2 新戊基新戊基neopentyl-CH2C(CH3)3 The following names are retained for unsubstituted radicals only: 下列未取代的基团的名称保留 4-Isobutyl-2,5-dimethylheptane 4-（2-methylpropyl)-2,5-dimethylheptane “异”（iso-）、“仲”(sec-)、“叔”（tert-）、“新”（neo-） Training n3,3-dimethylpentane n4-ethyl-2-methylhexane n4-ethy

11、l-2,2-dimethylhexane n4,4-diisopropylheptane n5,5-bis(l,2-dimethylpropyl)nonane 3,3-二甲基戊烷二甲基戊烷 2-甲基甲基-4-乙基已烷乙基已烷 2,2-二甲基二甲基-4-乙基已烷乙基已烷 4,4-二异丙基庚烷二异丙基庚烷 5,5-二（二（1,2-二甲基丙基）壬烷二甲基丙基）壬烷 Different or modified prefixes are used with complex substituents: bi -, tri -, tetra-; pUnsaturated unbranched acyclic

12、 hydrocarbons having are named by replacing the ending “-ane” of the name of the corresponding saturated hydrocarbon with the ending “-ene”. “-yne”. “-adiyne”, “- atriyne”. pIf there are two or more double bonds, the ending will be “-adiene”, “-atriene”. Alkenes and Alkynes pThe presence of one or m

13、ore double or triple bonds in an otherwise saturated parent hydride is denoted by changing the “-ane” ending of the name of a saturated parent hydride to one of the followings. One TwoThree Double bond-ene-ene-ene Triple bond-yne-yne-yne Alkenes and Alkynes pThe chain is so named as to give the poss

14、ible numbers to the . pOnly the of a double/triple bond is in the name of a compound. Rule-1、Rule-2 323 CHCHCHCHCH 323 CHCCCHCH or 2-pentene or 2-pentyne 323 CHCHCHCHCH Training 4-ethyl -2-methyl 2-ethylhex-1-ene 2-hexylbut CH3 CH3 CH3 CH3 Rule-3、4 双键和三键并存双键和三键并存 pThe presence of both double and tri

15、ple bonds is similarly denoted by endings such as “-enyne”, “-adienyne”, etc pNumbers as low as possible are given to double and triple bonds as a set, even though this may at times give “-yne” a lower number than “-ene”. pIf a choice remains, preference for low location is given to the double bonds

16、. Examples HCCC H CHCHCH2 CH3CHCHCCH Hex -5-yne Pent-1-yne CH3 CH2 CH 3-ethylpent-1-en-4-yne propyne 1-butyne or but-1-yne 2-butyne or but-2-yne 4-nonyne or non-4-yne 5,5-dimethyl-1-hexyne or 5,5-dimethylhex-1-yne 5-ethyl-5-methyl-3-octyne 5-ethyl-5-methyloct-3-yne 3-methyl-1,4-octadiyne or 3-methyl

17、octa-1,4-diyne 3-penten-1-yne or pent-3-en-1-yne 1 2 3 4 5 6 7 8 For the following molecules, give the correct name 9) 10) 11) 12) 13) 14) 15) trans-5-octen-2-yne or trans-oct-5-en-2-yne trans-3-hepten-1-yne or trans-hept-3-en-1-yne cis-5,6-dimethyl-3-octen-1-yne or cis-5,6-dimethyloct-3-en-1-yne 1-

18、hepten-6-yne or hept-1-en-6-yne 5-methyl-5-propyl-1-hepten-6-yne or 5-methyl-5-propylhept-1-en-6-yne cis-2-octen-4-yne or cis-oct-2-en-4-yne 3-butyl-4-methyl-1-octen-7-yne or 3-butyl-4-methyloct-1-en-7-yne Rule-5 nThe names of univalent radicals derived from unsaturated acyclic hydrocarbons have the

19、 endings “-enyl”, “-ynyl”, “- dienyl”， 不饱和烃基：将不饱和烃结尾的不饱和烃基：将不饱和烃结尾的“e”换为换为“yl” 常见不饱和一价基团常见不饱和一价基团 基团中文名基团英文名构造式 乙烯基 Vinyl (ethenyl) -CH=CH2 烯丙基 Allyl (2-propenyl) -CH2CH=CH2 乙炔基ethynylC CH 苯甲基(苄基)benzyl-CH2-C6H5 苯基phenyl-C6H5 环烷烃环烷烃 cyclic hydrocarbons p脂环烃：在相应链烃名前加上脂环烃：在相应链烃名前加上“cyclo-” cyclopentan

20、e cyclohexane cyclohexadiene cyclopropane Rule-1. pThe following names for monocyclic substituted aromatic hydrocarbons are retained. benzene isopropylbenzene methylbenzene toluene cumene Xylene (o-shown) Rule-2 pThe position of substituents is indicated by numbers p0-(ortho), m-(meta) and p-(para)

21、may be used in place of 1,2-, 1,3-, and 1,4-, respectively, when only two substituents are present 两个取代基的位置两个取代基的位置 邻邻(ortho-)、间、间(meta-)、对、对(para-) Example p邻 ortho-o- p间 meta-m- p对 para-p- o-xylene m-xylene p-xylene To name an by the IUPAC System: 醇的系统命名法 p脂肪族醇：将母体烃结尾的“e”改为“ol” p多元醇：“e”保留，“ol”前加羟基

22、数目 1,2-ethanediol 1,2,3-propanetriol Nomenclature of alcohols p习惯命名法 按氧原子所连接的两个烃基的名称命名 CH3-CH2CH3 ethyl methyl ether C2H5-C2H5ethyl ether/diethyl ether CH3-C(CH3)2 isopropyl methyl ether 醚醚 Nomenclature of Ethers 醚类的命名醚类的命名 Ethers are named by selecting the longest carbon chain as the parent compoun

23、d And naming the OR group as an alkoxy substituent . Common names for ethers are derived by specifying the alkyl groups attached to oxygen in alphabetical order and adding the word ether. C-C-O-C-C Ethoxyethane (diethyl ether) CH3OCH3 (CH3)2CHOCH(CH3)2 CH3OC(CH3)3 Dimethyl etherDiisopropyl ether Ter

24、t-butyl methyl ether Nomenclature of Amines 胺类的命名 The longest chain of carbon atoms that contains the amino group is taken as the Parent and NH2 is considered a substituent. Its presence is indicated by the prefix Amino-, and a number is used to show its location. If more one alkyl group is attached

25、 to nitrogen, the alkyl group containning the longest chain of carbon atoms is taken as the parent; other substiuents on nitrogen are named as alkyl groups and are preceded by N- to show that they are bonded to the nitrogen atom of the amine. CH3CH2NH2 aminoethane ( ethylamine ) (CH3)2CHCH2CH2NH2 1-

26、amino-3-methylbutane (isopentylamine) CH3CH2CH(CH3)CH2NHCH3 N-methyl-1-amino-2-methylbutane 1,6-diaminohexane (hexamethylenediamine) 1,5-diaminopentane (pentamethylenediamine; cadaverine 尸胺) 1,4-diaminobutane (tetramethylenediamine; putrescine 腐胺) Nomenclature of Amines 胺类的命名 苯胺 aniline 甲苯胺 toluidin

27、e Para- 对 Ortho- 邻 Meta- 间 铵盐 ammonium salt Tetramethylammonium hydroxide Trimethylphenylammonium ioide Amino- 胺 醛醛 p系统命名法：将烃词尾“e”换为“al” HCHO methanal CH3CH2CH2CHOpropanal Two classes of organic compounds that are similar in structure are and . p习惯命名法 -aldehyde HCHOformaldehyde (methanal) CH3CHO ace

28、taldehyde (ethanal) C6H5-CHObenzaldehyde 酮酮 p系统命名：将烃词尾的“e”换为“one” 丙酮 CH3COCH3 propan 丁酮 CH3CH2COCH3 butanone p习惯命名法：-ketone CH3COCH3 丙酮丙酮/ /二甲基酮 acetone(dimethyl) CH3COC2H5甲基乙基甲酮 methyl ethyl 乙基甲基甲酮 ethyl methyl Nomenclature of Carboxylic Acids 羧酸的命名 -oic acid 羧酸 Carboxylic acids that are derived fr

29、om openchainalkanes are systematically named by replacing the terminal eof the corresponding alkane name with oic acid. Compounds that have a COOH group bonded to a ring are named using the suffix carboxylic acid. The carboxylic acid carbon is attached to C1 and is not itself numbered in this system

30、. 羧酸羧酸 p系统命名：相应的烷烃去“e”“-oic acid” 甲酸 HCOOH methanoic acid 乙酸 CH3COOH ethanoic acid 丙酸 CH3CH2COOH propanoic acid p习惯命名法： HCOOH Formic acid CH3COOH Acetic acid CH3CH2COOH CH3CH2CHCH2COOH CH3 -甲基戊酸 (3-Methylpentanoic acid)(3-Methylpentanoic acid) CH2CH2CH2COOH -环己基丁酸（ -环己基酪酸） (4-Cyclohexylbutanoic acid)(4-Cyclohexylbutanoic acid) Aromatic acid p The simplest aromatic acid is . is known as , the basis for many drugs such as . OH O OH O OH