1、2022-4-221outlinenHydrocarbons （烃）（烃）nAlkyl Halides （卤代烷）（卤代烷）nAlcohols （醇）（醇）nKetones （酮）（酮）nAldehedye （醛）（醛）nCarboxylic acid （羧酸）（羧酸）nEthers （醚）（醚）nEsters （酯）（酯）nAmine （胺）（胺）nAmide （酰胺）（酰胺）3.1 Nomenclatures of Organic Compounds2022-4-222 The IUPAC nomenclature of organic chemistry is a systematic
2、method (系统方法）系统方法） of naming organic chemical compounds as recommended by the International Union of Pure and Applied Chemistry (IUPAC). Ideally, every possible organic compound should have a name from which an unambiguous structural formula can be drawn. There is also an IUPAC nomenclature of inorg
3、anic chemistry .2022-4-2231. Identify the parent hydrocarbon chain. This chain must follow the following rules, in order of precedence: It should have maximum substituents （取代基）（取代基）of the suffix functional group. It should have maximum number of multiple bonds. It should have the maximum length. It
4、 should have maximum number of double bondsIn chemistry, a number of prefixes(前缀）前缀）, suffixes （后缀）（后缀） and infixes are used to describe the type and position of functional groups in the compound.2022-4-2242.Identify the parent functional group, if any, with the highest order of precedence. 3.Identi
5、fy the side-chains. 4.Identify the remaining functional groups, if any, and name them by the name of their ions .5.Different side-chains and functional groups will be grouped together in alphabetical order. 6.Identify double/triple bonds. 7.Number the chain.Has the lowest locant for the suffix funct
6、ional group. Has the lowest locants for multiple bonds. Has the lowest locants for double bonds Has the lowest locants for prefixes 2022-4-2258.Number the various substituents and bonds with their locants. 9.Arrange everything like this: Group of side chains and secondary functional groups with numb
7、ers made in step 3 + prefix of parent hydrocarbon chain (eth, meth) + double/triple bonds with numbers (or ane) + primary functional group suffix with numbers.Wherever it says with numbers, it is understood that between the word and the numbers, you use the prefix(di-, tri-) 10.Add punctuation: Put
8、commas between numbers (2 5 5 becomes 2,5,5) Put a hyphen between a number and a letter (2 5 5 trimethylhexane becomes 2,5,5-trimethylhexane) Successive words are merged into one word (trimethyl hexane becomes trimethylhexane)2022-4-226The finalized name should look like this #,#-di-#-#-#,#,#-tri-#,
9、#-di-#-#-# is used for a number 2022-4-227Straight-chain alkanes take the suffix(后缀）后缀） -ane and are prefixed depending on the number of carbon atoms in the chain. CH4 methane; CH3(CH2) 7CH3 nonane 1. Straight-chain alkanes (直链烷烃直链烷烃)Hydrocarbons(烃烃)Number of carbons1234567nomenclatureMethaneEthaneP
10、ropaneButanePentaneHexaneHeptaneNumber of carbons891011121314nomenclatureOctaneNonaneDecaneUndecaneDodecaneTridecaneTetradecaneNumber of carbons152030405060nomenclaturePentadecaneEicosaneTriacontaneTetracontanepentacontanehexacontaneNumber of carbons708090100nomenclatureheptacontaneoctacontanenonaco
11、ntane HectaneNomenclature (系统命名法系统命名法) for some alkanes 3.1 Nomenclatures of Organic Compounds2022-4-228Triacontane三十烷三十烷Hentriacontane三十一烷三十一烷Dotriacontane 三十二烷三十二烷Tritriacontane 三十三烷三十三烷Tetratriacontane 三十四烷三十四烷.Hexatriacontane三十六烷三十六烷Heptatriacontane 三十七烷三十七烷Nonatriacontane三十九烷三十九烷Eicosane二十烷二十烷H
12、eneicosane 二十一烷二十一烷Docosane二十二烷二十二烷Tricosane二十三烷二十三烷Tetracosane二十四烷二十四烷Pentacosane二十五烷二十五烷Octacosane二十八烷二十八烷Nonacosane二十九烷二十九烷Tetracontane 四十烷四十烷Hentetracontane 四十一烷四十一烷Dotetracontane 四十二烷四十二烷Tetratetracontane 四十四烷四十四烷Hexatetracontane 四十六烷四十六烷Octatetracontane 四十八烷四十八烷Dopentacontane 五十二烷五十二烷Hexapenta
13、contane 五十六烷五十六烷Tetrapentacontane 五十四烷五十四烷一百烷一百烷 hectane一百一百三十三十二烷二烷 dotricontahectane Decane 十烷十烷2022-4-229The naming convention for alkyls is much the same as alkanes. The suffix（后缀）（后缀） is always -yl. 2. alkyls(烷基烷基)Number of carbons123456789101112Prefixmeth-eth-prop-but-pent-hex-hept-oct-non-dec
14、-undec-dodec-Molecule nameMethylEthylpropylButylpentylhexylheptyloctylnonyldecylundecyldodecyl2,3,3-trimethylpentane Hydrocarbons3.1 Nomenclatures of Organic Compounds表示基团个数：表示基团个数：mono-, di-, tri-, tetra-, penta-, hexa- 2022-4-2210Prefix（前缀）（前缀） of alkyls: n-（正）（正）, iso-(异）异）, sec（仲）（仲）-, tert（叔）（叔
15、）- Hydrocarbons3.1 Nomenclatures of Organic Compoundsn: normal; sec: secondary (仲）仲）; tert: tertiary （叔）（叔）-CH2CH2CH2CH3CH3H2CCHCH3CH3CH2CH3CCH3H3CCH3CCH2CH3H3Cn-butyliso-butylsec-butyltert-butyltert-pentylH3CCHCH2CH3iso-pentylCH3仲丁基仲丁基叔丁基叔丁基叔戊基叔戊基异戊基异戊基异丁基异丁基正丁基正丁基2022-4-2211(CH3) 2CHCH3：isobutane,
16、 2-methylpropane. iso: a methyl group bonded to the middle (2) carbon, and given the systematic name 2-methylpropane. 3. Branched alkanes Hydrocarbons3.1 Nomenclatures of Organic Compounds2-甲基丙烷甲基丙烷3-甲基甲基-4-丙基丙基-辛烷辛烷4-甲基甲基-3-乙基乙基-己烷己烷If a chemical has different substituents, the substituents are ord
17、ered alphabetically .2022-4-2212If several groups of the same kind are attached to the main chain, list the groups only once using the appropriate numerical prefix di, tri, tetra, penta, hexa, hepta, octa, nona, deca etc. to indicate how many times that side group appears.a) Hyphens (连字号）连字号） must s
18、eparate numbers and lettersb) Commas（逗号）（逗号） must separate numbersc) the di, tri, tetra etc. are not included in the alphabetizing process.d) n, s, and t are not included in the alphabetizing process, but iso is5-ethyl-2,3-dimethylheptane2022-4-2213Check 1: Please give name to the following structur
19、esCCH3CH3CH2CH3CCH3CH3CH3CCH3CH3CHCH2CH2CH3CH3CH32,2,4,4-tetrametylpetane2,3,3-trimetylhexane2,2,4,4-四甲基戊烷四甲基戊烷2,3,3-三甲基己烷三甲基己烷2022-4-2214CyclopropaneCyclobutaneCyclopentaneCyclohexaneCyclic alkanes are simply prefixed with cyclo-, 4. Cyclic alkanes2022-4-2215CH3CH3CH3CH3CH31,2-dimethylcyclobutaneme
20、thylcyclopropane1,3-dimethylcyclohexaneCH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH3CH31,2-dimethylcyclobutanemethylcyclopropane1,3-dimethylcyclohexaneCH3CH3CH3CH3CH3CH3CH3CH3CH3CH31-methylcyclopentaneCheck 2: Please give name to the following structures1,2-1,2-二甲基环丁烷二甲基环丁烷1-1-甲基环戊烷甲基环戊烷1,2-1,2-二甲基环己烷二
21、甲基环己烷2022-4-2216CH3CH2CH2CHCH2CHCH2CH2CH3CH3CHCH3CH2CH2CH3CH3CH2CHCHCHCH3CHCH3CH3CH3CH2CH2CH313245672,3,5-三甲基三甲基-4-丙基庚烷丙基庚烷have maximum substituents7986543214-isopropyl-6-propylnonane4-丙基丙基-6-异丙基壬烷异丙基壬烷2,3,5-trimethyl-4-propylheptanehave maximum lengthC H3C H2C HC HC H2C HC H3C H3C H3C H2C HC H3C H3
22、1234567the lowest locants for prefixes2, 5-dimethyl-4-isobutylheptane2, 5-二甲基二甲基-4-异丁基庚烷异丁基庚烷2022-4-2217 Halogen（卤素）（卤素） functional groups are prefixed with the bonding position and take the form fluoro-（氟（氟-）, chloro-（氯（氯-）, bromo-（溴（溴-）, iodo-（碘（碘-）, etc., depending on the halogen. Multiple groups
23、 are dichloro-, trichloro-, etc, and dissimilar groups are ordered alphabetically as before. CHCl3 (chloroform) : trichloromethane. The anesthetic （麻醉的）（麻醉的）Halothane (氟氟烷烷 ,CF3CHBrCl): 2-bromo-2-chloro-1,1,1-trifluoroethane.5. Halogens (Alkyl Halides 卤代烃卤代烃)3.1 Nomenclatures of Organic Compounds1,1
24、,1-三氟三氟-2-氯氯-2-溴溴-乙烷乙烷氯仿氯仿三氯甲烷三氯甲烷CH3CH2CHCHCH2CH3Cl Br3_4_氯溴己烷3-bromo-4-chlorohexane2022-4-2218Check 3: Please give name to the following structuresCH3CH2CHCH2CHCH2CH3CH3Cl3_5_氯庚烷甲基3-chloro-5-methylheptaneCH3CHCHCHCH3FCH3CH31324567132455-fluoro-2,3-dimethylpentane2,3-二甲基二甲基-5-氟戊烷氟戊烷2022-4-22196. Al
25、kenes(烯烃烯烃) and Alkynes(炔烃炔烃) Alkenes are named for their parent alkane chain with the suffix -ene and an infixed number indicating the position of the double-bonded carbon in the chain: CH2=CHCH2CH3 is but-1-ene. Hydrocarbons3.1 Nomenclatures of Organic Compoundscyclohexenepenta-1,3-dienecyclohexen
26、e7,7-dimethyl-4-propylnon-2-ene 2022-4-2220Alkynes are named using the same system, with the suffix -yne indicating a triple bond: ethyne (acetylene), propyne (methylacetylene).6,6-diethyl-oct-3-yneAcetylene bond (炔鍵炔鍵 ), triple bond 2022-4-22212,4-dimethylhexane5-ethyl-3,3-dimethylhept-1-ene(not 3-
27、ethyl-5,5-dimethylhept-6-ene)Check 4: Please give name to the following structures12345612345672022-4-2222Alcohols (R-OH) take the suffix -ol with an infix numerical bonding position: CH3CH2CH2OH is propan-1-ol. The suffixes -diol, -triol, -tetraol, etc., are used for multiple -OH groups: Ethylene g
28、lycol CH2OHCH2OH is ethane-1,2-diol.2. Alcohols(醇醇)If higher precedence functional groups are present (see order of precedence, below), the prefix hydroxy is used with the bonding position. CH3CHOHCOOH is 2-hydroxypropanoic acid.3.1 Nomenclatures of Organic Compoundsethan-1,2-diol 2022-4-2223pentan-
29、2-ol1,1,1-trichloro-3,3-dimethylhexan-2-olCyclohexan-1,2-diolCheck 5: Please give name to the following structures2022-4-2224 Ethers (R-O-R) consist of an oxygen atom between the two attached carbon chains. The shorter of the two chains becomes the first part of the name with the -ane suffix changed
30、 to -oxy, and the longer alkane chain become the suffix of the name of the ether. If the oxygen is not attached to the end of the main alkane chain, then the whole shorter alkyl-plus-ether group is treated as a side-chain and prefixed with its bonding position on the main chain. Thus CH3OCH(CH3)2 is
31、 2-methoxypropane.(not ethoxymethane).3. Ethers(醚醚)3.1 Nomenclatures of Organic Compounds2022-4-22254-ethoxy-2-methylhexaneCheck 6: Please give name to the following structuresOCl2-methoxy-3-chloropentaneOisopropoxybutane2022-4-2226 Aldehydes (R-CHO) take the suffix -al. If other functional groups a
32、re present, the chain is numbered such that the aldehyde carbon is in the 1 position. If a prefix form is required, oxo- is used (as for ketones), with the position number indicating the end of a chain: CHOCH2COOH is 3-oxopropanoic acid. If the carbon in the carbonyl group cannot be included in the
33、attached chain (for instance in the case of cyclic aldehydes), the prefix formyl- or the suffix -carbaldehyde is used: C6H11CHO is cyclohexanecarbaldehyde.4. Aldehydes(醛醛)3.1 Nomenclatures of Organic CompoundsCH3C=CHCH2CH2CHOCH35-methyl-4-en-hexal5-甲基甲基-4-己烯醛己烯醛4-(Benzyloxy)- 3-formyl(1,1-biphenyl)-
34、3-carboxylic acid 4-(苯氧基）苯氧基）-3-甲酰甲酰(1,1-联苯联苯)-3-羧酸羧酸 2022-4-2227 In general ketones (R-CO-R) take the suffix -one (pronounced own, not won) with an infix position number: CH3CH2CH2COCH3 is pentan-2-one. If a higher precedence suffix is in use, the prefix oxo- is used.5. Ketones(酮酮)CH3CH2CH2COCH2CHO
35、 3-oxohexanal3.1 Nomenclatures of Organic Compounds2022-4-2228In general carboxylic acids are named with the suffix -oic acid. As for aldehydes, they take the 1 position on the parent chain. For carboxylic acids attached to a benzene ring such as Ph-COOH, these are named as benzoic acid or its deriv
36、atives.If there are multiple carboxyl groups on the same parent chain, the suffix -carboxylic acid can be used (as -dicarboxylic acid, -tricarboxylic acid, etc.). In these cases, the carbon in the carboxyl group does not count as being part of the main alkane chain. 6. Carboxylic acids(羧酸羧酸)Citric a
37、cid (柠檬酸）柠檬酸）2-hydroxypropane- 1,2,3-tricarboxylic acid3.1 Nomenclatures of Organic Compounds2-(trifluoromethyl)benzoic acid 2022-4-22293-chloro-3-methylbutanal3,4-dibromobutan-2-one2-pentanonecyclohexanoneCheck 7: Please give name to the following structures2022-4-22307. Esters(酯酯)Esters (R-CO-O-R)
38、 are named as alkyl derivatives of carboxylic acids. The alkyl (R) group is named first. The R-CO-O part is then named as a separate word based on the carboxylic acid name, with the ending changed from -oic acid to -oate. CH3CH2CH2CH2COOCH3 is methyl pentanoate, (CH3) 2CHCH2CH2COOCH2CH3 is ethyl 4-m
39、ethylpentanoate. For esters such as ethyl acetate (CH3COOCH2CH3), ethyl formate (HCOOCH2CH3) or dimethyl phthalate that are based on common acids, IUPAC recommends use of these established names, called retained names. The -oate changes to -ate. Some simple examples, named both ways, are shown in th
40、e figure above 3.1 Nomenclatures of Organic Compoundsdimethyl phthalate2022-4-2231If the alkyl group is not attached at the end of the chain, the bond position to the ester group is infixed before -yl: CH3CH2CH(CH3)OOCCH2CH3 may be called but-2-yl propanoate or but-2-yl propionate Esters(酯酯)3.1 Nome
41、nclatures of Organic Compoundspropionic acid - 丙酸丙酸2022-4-22322,2,2-trifluoroethanoic acid1,2-ethanedioic acid(oxalic acid 草酸草酸)Isopropyl 2,2-dimethylbutanoateCheck8: Please give name to the following structures2022-4-2233. 8. Amines(胺胺)3.1 Nomenclatures of Organic Compounds2-butanaminecyclohexanami
42、nePrimary Amines (伯胺，伯胺，R-NH2) are named for the attached alkane chain with the suffix “-amine” (e.g. CH3NH2 methanamine). If necessary, the bonding position infixedIf higher precedence functional groups are present (see order of precedence, below), the prefix “amino is used with the bonding positio
43、n2022-4-2234diethylamineFor secondary amines (仲胺）仲胺） (of the form R-NH-R), the longest carbon chain attached to the nitrogen atom becomes the primary name of the amine; the other chain is prefixed as an alkyl group with location prefix given as an italic （斜体的）（斜体的） N : CH3NHCH2CH3 is N-methylethanam
44、ine. 乙二胺乙二胺N-甲基乙胺甲基乙胺N-甲基甲基-N-乙基丙胺乙基丙胺N-ethylethanamine2022-4-2235trimethylaminetriphenylamineTertiary amines (叔胺，叔胺，R-NR-R) are treated similarly: CH3CH2N(CH3)CH2CH2CH3 is N-ethyl-N-methylpropanamine. Again, the substituent groups are ordered alphabetically. 三甲胺三甲胺三苯胺三苯胺2022-4-2236N-methylpropan-1-
45、amineN-ethyl-N-methylbutan-1-amineN,N-dimethylbutan-2-amineCheck 9: Please give name to the following structures2022-4-2237 Amides (R-CO-NH2) take the suffix -amide. There is no prefix form, and no location number is required since they always terminate a carbon chain, e.g. CH3CONH2 (acetamide) is n
46、amed ethanamide.Secondary and tertiary amides are treated similarly to the case of amines: alkane chains bonded to the nitrogen atom are treated as substituents with the location prefix N: HCON(CH3)2 is N,N-dimethylmethanamide.9. Amides(酰胺酰胺)3.1 Nomenclatures of Organic Compounds2022-4-2238N-methylp
47、ropanamideN,N-dimethylpropanamideN-isopropyl-N-methylbut-2-en-amideCheck 10: Please give name to the following structures2022-4-2239Benzene is the most common aromatic parent structure. a. The benzene ring is named as a phenyl group when it is a substituent. b. Multiple substituents on a benzene rin
48、g are numbered to give these substituents the lowest possible numbers. When only two substituents are attached to a benzene ring, they can be named by the common nomenclature using ortho (o-) (1-2 placement), meta (m-) (1-3 placement) or para (p-) (1-4 placement).ortho-xylene10. Aromatic hydrocarbon
49、(芳香烃）芳香烃）Phenylethynebenzenemeta-xylenepara-xylene2022-4-2240Select the names for each structure:1. Chlorocyclohexane2. Chlorobenzene3. 1-chlorobenzene1. Meta-methyltoluene2. Meta-dimethylbenzene3. 1,3-dimethylbenzeneCH3CH3ClCheck 11: Please give name to the following structures2022-4-2241ClClCH3Cl1
50、,3-diethyl-2-methylbenzene1,3-dichlorobenzene Ortho-chlorotoluene1-ethyl-2-methylbenzene1-methyl-3-vinyl - benzenevinyl ：乙烯基：乙烯基2022-4-2242anthracenephenanthrenea -isopropylnaphthalene 1-ethyl-5-methylnaphthalene 1-methylnaphthalene -methylnaphthalene 2-ethenylnaphthalene -vinylnaphthalenenaphthalen
