有機(jī)化合物的命名

1、Polymer ChemistryShuizhu Wu 吳水珠吳水珠(Prof. PhD)Department of Polymer Sci. & Eng.E-mail: Tel: 22236262Books Principles of Polymerisation G Odian Polymer Synthesis P Rempp and E W Merrill Polymers: Chemistry & Physics of Modern Materials J M G Cowie Polymer Chemistry : An Introduction G Challa I

2、ntroduction to Polymers R J Young and P A Lovell IUPAC Nomenclature of organic compoundsA. Alkanes, alkyl halides, alcohols and cycloalkanes（烷烴、鹵代烴、醇、環(huán)烷烴）（烷烴、鹵代烴、醇、環(huán)烷烴） Nomenclature of alkyl groups AlkaneAlkyl group AbbreviationCH4, methaneMethylMe甲基甲基CH3CH3, ethaneEthylEt乙基乙基PropanePropylPr丙基丙基Buta

3、neButylBu丁基丁基The unbranched alkanesMethane 1 Decane 10Ethane 2 Undecane 11Propane 3 Dodecane 12Butane 4 Tridecane 13Pentane 5 Tetradecane 14Hexane 6 Pentadecane 15Heptane 7 Hexadecane 16Octane 8 Heptadecane 17Nonane 9 Octadecane 18Nonadecane 19 Eicosane 20Propyl isopropylButyl isobutyl sec-butyl ter

4、t-butylNomenclature of branched-chain alkanesLocate the longest continuous chain of carbon atoms; this chain determines the base name for the alkane.Number the longest chain beginning with the end of the chain nearer the substituent. 6 5 4 3 2 1 CH3CH2CH2CH2CHCH31. CH3 substituent3. Use the numbers

5、obtained by application of rule 2 to designate the location of the substituent group. 2-methylhexane2-甲基己烷甲基己烷4. When two or more substituents are present, give each substituent a number corresponding to its location on the longest chain.5. When two or more substituents are presnt on the same carbon

6、 atom, use that number twice. 3-ethyl-3-methylhexane3- 3-甲基甲基-3-3-乙基己烷乙基己烷6. When two or more substituents are identical, indicate this by the use of the prefixes di-, tri-, tetra-, and so on.7. When two chains of equal length compete for selection as the base chain, choose the chain with the greate

7、r number of substituents.8. When branching first occurs at an equal distance from either end of the longest chain, choose the name that gives the lower number at the first point of difference. Nomenclature of alkyl halideHaloalkaneChloroethane CH3CH2Cl氯代乙烷氯代乙烷2-bromopropane CH3CH(Br)CH32-溴丙烷溴丙烷Commo

8、n nomenclature: alkyl halide for example ethyl chloride氯代乙烷氯代乙烷 isopropyl bromide溴代異丙烷溴代異丙烷Nomenclature of alcoholSelect the longest continuous carbon chain to which the hydroxyl is directly attached. Change the name of the alkane corresponding to this chain by dropping the final e and adding ol. Th

9、is gives the base name of the alcohol.1.Number the longest continuous carbon chain so as to give the carbon atom bearing the hydroxyl group the lower number. Indicate the position of the hydroxyl group by using this number; indicate the positions of other substituents by using the numbers correspond

10、ing to their positions along the carbon chain.For example: CH3CH2CH2OH 1-propanol1-丙醇丙醇 CH3CH(OH)CH2CH3 2-butanol1-丁醇丁醇 Nomenclature of cycloalkanesCyclopropane 環(huán)丙烷環(huán)丙烷 cyclopentane環(huán)戊烷環(huán)戊烷Isopropylcyclohexane 異丙基環(huán)丙烷異丙基環(huán)丙烷 chlorocyclopentane氯代環(huán)戊烷氯代環(huán)戊烷 Occasionally, it is convenient and appropriate to n

11、ame cycloalkyl groups as substituents on alkane chains or on other rings.B. Nomenclature of alkenes, cycloalkenes and alkynes烯烴、環(huán)烯烴、炔烯烴、環(huán)烯烴、炔Nomenclature of alkenes and cycloalkenesDetermine the base name by selecting the longest chain that contains the double bond and change the ending of the name

12、of the alkane of identical length from ane to ene.1.Number the chain so as to include both carbon atoms of the doulbe bond, and begin numbering at the end of the chain nearer the double bond. Designate the location of the double bond by using the number of the first atom of the double bond as a pref

13、ix. CH2=CHCH2CH3 1-butene1-丁烯（丁烯（butane)3. Indicate the location of the substituent groups by the numbers of the carbon atoms to which they are attached.CH3(CH3)C=CHCH3 2-methyl-2-butene 2-甲基甲基-2-丁烯丁烯4. Number substituted cycloalkenes in the way that gives the carbon atoms of the double bond the 1-

14、and 2- positions and that also gives the substituent groups the lower numbers at the first point of difference. 1-methylcyclopentene1-甲基環(huán)戊烯甲基環(huán)戊烯5. Two frequently encountered alkenyl groups are the vinyl group and the allyl groupCH2=CH- CH2=CHCH2-6. Designate the geometry of a double bond with two id

15、entical groups with the prefixes cis- and trans-. If two identical groups are on the same side of the double bond, it is cis; if they are on the opposite sides, it is trans.cis-2-pentene 順式-2-戊烯 trans-2-pentene 反式-2-戊烯Nomenclature of alkynes炔炔Unbranched alkynes are named by replacing the ane of the

16、name of the corresponding alkane with the ending yne. The chain is numbered in order to give the carbon atoms of the triple bond the lowest possible number.The lower number of the two carbon atoms of the triple bond is used to designate the location of the triple bond.The locations of substituent gr

17、oups of branched alkynes and substituted alkynes are also indicated with numbers.1. ClCH2CCH 3-chloropropyne3-氯代丙炔氯代丙炔Nomenclature of benzene derivatives苯衍生物苯衍生物In certain compounds, benzene is the parent name and the substituent is simply indicated by a prefix. fluorobenzene 氟代苯氟代苯 chlorobenzene 氯氯

18、苯苯 bromobenzene溴代苯溴代苯 nitrobenzene硝硝基苯基苯2. For other compounds, the substituent and the benzene ring taken together may form a new parent name. Methylbenzene is usually called toluene, hydroxybenzene is almost always called phenol, and aminobenzene is almost always called aniline. Benzenesulfonic ac

19、id 苯磺酸苯磺酸 benzoic acid苯甲酸苯甲酸3. When two substituents are present, their relative positions are indicated by the prefixes ortho, meta and para (abbreviated o-, m- and p-) or by the use of numbers. 1,2-dibromobenzene 1,2-二溴苯二溴苯 or o-dibromobenzene鄰二溴苯鄰二溴苯4. Numbers are used for two or more substituent

20、s, but orthor, meta and para must never be used for more than two substiuents.2-nitrobenzoic acid 2-硝基苯甲酸硝基苯甲酸 1,2-dimethylbenzene (or o-xylene) 1,2-二甲基二甲基苯（或鄰二甲苯）苯（或鄰二甲苯）The dimethylbenzenes are called xylene.5. When benzene ring is named as a substituent, it is called a phenyl group. The phenyl gr

21、oup is often abbreviated as C6H5-, Ph-, or -,6. The name benzyl is reserved for the group derived from toluene by the removal of one hydrogen atom of the methyl group.D. Nomenclature of phenols苯酚苯酚In many compounds, phenol is the base name. 4-chlorophenol 4-氯苯酚氯苯酚 2-nitrophenol 2-硝基苯酚硝基苯酚 3-bromophe

22、nol3-溴苯酚溴苯酚2. The methylphenols are commonly called cresols. 2-methylphenol 2-甲基苯酚甲基苯酚(o-cresol鄰甲酚鄰甲酚) 3-methylphenol 3-甲基苯酚甲基苯酚(m-cresol間甲酚間甲酚) 4-methylphenol 4-甲基苯酚甲基苯酚(p-cresol對(duì)甲酚對(duì)甲酚)3. The benzenediols also have common names. 1,2-benzenediol (catechol鄰苯二酚、兒茶酚鄰苯二酚、兒茶酚) 1,3-benzenediol (resorcinol

23、間苯二酚、雷鎖間苯二酚、雷鎖酚酚) 1,4-benzenediol (hydroquinone對(duì)苯二酚對(duì)苯二酚)E. Nomenclature of aldehydes and ketones醛和酮醛和酮Nomenclature of aldehydes醛醛In the IUPAC system we name aliphatic aldehydes substitutively by replacing the final e of the name of the corresponding alkane with al.Since the aldehyde group must be at

24、 the end of the chain of carbon atoms, there is no need to indicate its position.When other substituents are present, however, we must designate the carbonyl group carbon as position 1.1.Many aldehydes also have common names; these names are given here in parentheses.These common names are derived f

25、rom the corresponding carboxylic acids and some of them are retained by the IUPAC as acceptable names. methanal (formaldehyde甲醛甲醛) ethanal(acetaldehyde乙醛乙醛) propanal (propionaldehyde丙醛丙醛) 5. When the carbonyl group is attached to an aromatic ring, we name the compound as a benzaldehyde苯甲醛苯甲醛, tolual

26、dehyde甲苯甲醛甲苯甲醛, naphthaldehyde萘甲醛萘甲醛, and so on.Nomenclature of ketones酮酮We name aliphatic ketones substitutively by replacing the final e of the name of the corresponding alkane with one. We then number the chain in the way that gives the carbonyl carbon atom the lower possible number, and we use t

27、his number to designate its position. 2-propanone(acetone丙酮丙酮) 2-butone (ethyl methyl ketone丁酮、甲乙酮丁酮、甲乙酮) 2-pentanone(methyl propyl ketone2-戊戊酮、甲丙酮酮、甲丙酮)1.3. Common names for ketones (in parentheses) are obtained simply by separately naming the two groups attached to the carbonyl group and adding th

28、e word ketone as a separate word.4. Some aryl ketones have special names. acetophenone 苯乙酮苯乙酮(methyl phenyl ketone苯基苯基甲基甲酮甲基甲酮) benzophenone苯甲酮苯甲酮 (diphenyl ketone二苯基酮二苯基酮)5. When we find it necessary to name the aldehyde group as a substituent, we call it the methanoyl or formyl 甲酰氧基甲酰氧基group. It i

29、s often written CHO. Whe RCO- groups are named as substituents, they are called alkanoyl or acyl酰酰基基 groups.F. Nomenclature of carboxylic acids羧羧酸酸IUPAC systematic or substitutive names for carboxylic acids are obtained by dropping the final e of the name of the alkane corresponding to the longest c

30、hain in the acid and by adding oic acid. The carboxyl carbon atom is assigned number 1. 4-methylhexanoic acid 4-甲基己酸甲基己酸 4-hexenoic acid3. Many carboxylic acids have common names that are derived from Latin or Greek words that indicate one of their natural sources. Methanoic acid is called fromic ac

31、id 蟻酸蟻酸(from Latin, formica or ant). Ethanoic acid is called acetic acid 醋酸醋酸(from Latin, acetum or vinegar). Butanoic acid is one compound responsible for the odor of rancid butter, thus its common name is butyric acid 丁酸丁酸(from Latin, butyrum or butter). Hexanoic acid is one compound associated wi

32、th the odor of goats, hence its common name, caproic acid (from Latin Caper, or goat).Pentanoic acid, as a result of its occurrence in valerian, a perennial herb, is named valeric acid.Octadecanoic acid 十八酸十八酸t(yī)akes its common name, stearic acid硬酯酸硬酯酸, form the Greek word Stear, for tallow (牛油).4. Mo

33、st of the above common names have been with us for a long time. In almost all other instances, we shall use IUPAC systematic or substitutive names. Carboxylic salts Salts of carboxylic acids are named as ates; in both common and systematic names, -ate replaces ic acid.Thus CH3COONa is sodium acetate

34、 or sodium ethanoate.Vinyl acetate CH3COOCH=CH2醋酸乙烯酯醋酸乙烯酯Methyl acrylate 丙烯酸甲酯丙烯酸甲酯 acrylic acid（丙烯酸丙烯酸）H. Nomenclature of amines胺胺In common nomenclature most primary amines are called alkylamines.In systematic nomenclature (in parentheses below) they are named by adding the suffix -amine to the name of the chain or ring system to which the NH2 group is attached with elisi