1、2019/5/7,1,3.1 Nomenclatures of Organic Compounds,3 Nomenclatures of Chemicals,2019/5/7,2,outline,Hydrocarbons （烃） Alkyl Halides （卤代烷） Alcohols （醇） Ketones （酮） Aldehedye （醛） Carboxylic acid （羧酸） Ethers （醚） Esters （酯） Amine （胺） Amide （酰胺）,3.1 Nomenclatures of Organic Compounds,2019/5/7,3,The IUPAC no
2、menclature of organic chemistry is a systematic method (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. T
3、here is also an IUPAC nomenclature of inorganic chemistry .,2019/5/7,4,1. Identify the parent hydrocarbon chain. This chain must follow the following rules, in order of precedence: It should have maximum substituents （取代基）of the suffix functional group. It should have maximum number of multiple bond
4、s. It should have the maximum length. It should have maximum number of double bonds,In chemistry, a number of prefixes(前缀）, suffixes （后缀） and infixes are used to describe the type and position of functional groups in the compound.,2019/5/7,5,Identify the parent functional group, if any, with the hig
5、hest order of precedence. Identify the side-chains. Identify the remaining functional groups, if any, and name them by the name of their ions . Different side-chains and functional groups will be grouped together in alphabetical order. Identify double/triple bonds. Number the chain. Has the lowest l
6、ocant for the suffix functional group. Has the lowest locants for multiple bonds. Has the lowest locants for double bonds Has the lowest locants for prefixes,2019/5/7,6,Number the various substituents and bonds with their locants Arrange everything like this:Group of side chains and secondary functi
7、onal groups with numbers 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-
8、) Add punctuation: Put 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),2019/5/7,7,The finalized name should look like thi
9、s,#,#-di-#-#-#,#,#-tri-#,#-di-#-#-,# is used for a number,2019/5/7,8,Straight-chain alkanes take the suffix(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),Hydrocarbons(烃),Nomenclature (系统命名法) for so
10、me alkanes,3.1 Nomenclatures of Organic Compounds,2019/5/7,9,Triacontane三十烷 Hentriacontane三十一烷 Dotriacontane 三十二烷 Tritriacontane 三十三烷 Tetratriacontane 三十四烷. Hexatriacontane三十六烷 Heptatriacontane 三十七烷 Nonatriacontane三十九烷,Eicosane二十烷 Heneicosane 二十一烷 Docosane二十二烷 Tricosane二十三烷 Tetracosane二十四烷 Pentacosa
11、ne二十五烷 Octacosane二十八烷 Nonacosane二十九烷,Tetracontane 四十烷 Hentetracontane 四十一烷 Dotetracontane 四十二烷 Tetratetracontane 四十四烷 Hexatetracontane 四十六烷 Octatetracontane 四十八烷,Dopentacontane 五十二烷 Hexapentacontane 五十六烷 Tetrapentacontane 五十四烷,一百烷 hectane 一百三十二烷 dotricontahectane,Decane 十烷,2019/5/7,10,The naming con
12、vention for alkyls is much the same as alkanes. The suffix（后缀） is always -yl.,2. alkyls(烷基),2,3,3-trimethylpentane,Hydrocarbons,3.1 Nomenclatures of Organic Compounds,表示基团个数：mono-, di-, tri-, tetra-, penta-, hexa-,2019/5/7,11,Prefix（前缀） of alkyls: n-（正）, iso-(异）, sec（仲）-, tert（叔）-,Hydrocarbons,3.1 N
13、omenclatures of Organic Compounds,n: normal; sec: secondary (仲）; tert: tertiary （叔）,CH3,仲丁基,叔丁基,叔戊基,异戊基,异丁基,正丁基,2019/5/7,12,(CH3) 2CHCH3：isobutane, 2-methylpropane. iso: a methyl group bonded to the middle (2) carbon, and given the systematic name 2-methylpropane.,3. Branched alkanes,Hydrocarbons,3.
14、1 Nomenclatures of Organic Compounds,2-甲基丙烷,3-甲基-4-丙基-辛烷,4-甲基-3-乙基-己烷,If a chemical has different substituents, the substituents are ordered alphabetically .,2019/5/7,13,If several groups of the same kind are attached to the main chain, list the groups only once using the appropriate numerical prefi
15、x di, tri, tetra, penta, hexa, hepta, octa, nona, deca etc. to indicate how many times that side group appears.,a) Hyphens (连字号） must separate numbers and letters b) Commas（逗号） must separate numbers c) the di, tri, tetra etc. are not included in the alphabetizing process. d) n, s, and t are not incl
16、uded in the alphabetizing process, but iso is,5-ethyl-2,3-dimethylheptane,2019/5/7,14,Check 1: Please give name to the following structures,2,2,4,4-tetrametylpetane,2,3,3-trimetylhexane,2,2,4,4-四甲基戊烷,2,3,3-三甲基己烷,2019/5/7,15,Cyclopropane,Cyclobutane,Cyclopentane,Cyclohexane,Cyclic alkanes are simply
17、prefixed with “cyclo-“,4. Cyclic alkanes,2019/5/7,16,1-methylcyclopentane,Check 2: Please give name to the following structures,1,2-二甲基环丁烷,1-甲基环戊烷,1,2-二甲基环己烷,2019/5/7,17,2,3,5-三甲基-4-丙基庚烷,have maximum substituents,4-isopropyl-6-propylnonane,4-丙基-6-异丙基壬烷,2,3,5-trimethyl-4-propylheptane,have maximum le
18、ngth,2019/5/7,18,Halogen（卤素） functional groups are prefixed with the bonding position and take the form fluoro-（氟-）, chloro-（氯-）, bromo-（溴-）, iodo-（碘-）, etc., depending on the halogen. Multiple groups are dichloro-, trichloro-, etc, and dissimilar groups are ordered alphabetically as before. CHCl3 (
19、chloroform) : trichloromethane. The anesthetic （麻醉的）Halothane (氟烷 ,CF3CHBrCl): 2-bromo-2-chloro-1,1,1-trifluoroethane.,5. Halogens (Alkyl Halides 卤代烃),3.1 Nomenclatures of Organic Compounds,1,1,1-三氟-2-氯-2-溴-乙烷,氯仿 三氯甲烷,3-bromo-4-chlorohexane,2019/5/7,19,Check 3: Please give name to the following stru
20、ctures,3-chloro-5-methylheptane,2019/5/7,20,6. Alkenes(烯烃) and Alkynes(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.,Hydrocarbons,3.1 Nomenclatures of Organ
21、ic Compounds,cyclohexene,penta-1,3-diene,cyclohexene,7,7-dimethyl-4-propylnon-2-ene,2019/5/7,21,Alkynes are named using the same system, with the suffix “-yne“ indicating a triple bond: ethyne (acetylene), propyne (methylacetylene).,6,6-diethyl-oct-3-yne,Acetylene bond (炔鍵 ), triple bond,2019/5/7,22
22、,2,4-dimethylhexane,5-ethyl-3,3-dimethylhept-1-ene (not 3-ethyl-5,5-dimethylhept-6-ene),Check 4: Please give name to the following structures,2019/5/7,23,Alcohols (R-OH) take the suffix “-ol“ with an infix numerical bonding position: CH3CH2CH2OH is propan-1-ol. The suffixes -diol, -triol, -tetraol,
23、etc., are used for multiple -OH groups: Ethylene glycol CH2OHCH2OH is ethane-1,2-diol.,2. Alcohols(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
24、of Organic Compounds,ethan-1,2-diol,2019/5/7,24,pentan-2-ol,1,1,1-trichloro-3,3-dimethylhexan-2-ol,Cyclohexan-1,2-diol,Check 5: Please give name to the following structures,2019/5/7,25,Ethers (R-O-R) consist of an oxygen atom between the two attached carbon chains. The shorter of the two chains beco
25、mes the first part of the name with the -ane suffix changed 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 i
26、ts bonding position on the main chain. Thus CH3OCH(CH3)2 is 2-methoxypropane.,(not ethoxymethane).,3. Ethers(醚),3.1 Nomenclatures of Organic Compounds,2019/5/7,26,4-ethoxy-2-methylhexane,Check 6: Please give name to the following structures,2-methoxy-3-chloropentane,O,isopropoxybutane,2019/5/7,27,Al
27、dehydes (R-CHO) take the suffix “-al“.If other functional groups are 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
28、 acid. If the carbon in the carbonyl group cannot be included in the 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),3.1 Nomenclatures of Organic Compounds,5-methyl-4-en-he
29、xal,5-甲基-4-己烯醛,4-(Benzyloxy)- 3-formyl(1,1-biphenyl)-3-carboxylic acid,4-(苯氧基）-3-甲酰(1,1-联苯)-3-羧酸,2019/5/7,28,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
30、 “oxo-“ is used.,5. Ketones(酮),CH3CH2CH2COCH2CHO 3-oxohexanal,3.1 Nomenclatures of Organic Compounds,2019/5/7,29,In 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
31、Ph-COOH, these are named as benzoic acid or its derivatives.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 t
32、he main alkane chain.,6. Carboxylic acids(羧酸),Citric acid (柠檬酸）,2-hydroxypropane- 1,2,3-tricarboxylic acid,3.1 Nomenclatures of Organic Compounds,2-(trifluoromethyl)benzoic acid,2019/5/7,30,3-chloro-3-methylbutanal,3,4-dibromobutan-2-one,2-pentanone,cyclohexanone,Check 7: Please give name to the fol
33、lowing structures,2019/5/7,31,7. Esters(酯),Esters (R-CO-O-R) 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
34、 is methyl pentanoate, (CH3) 2CHCH2CH2COOCH2CH3 is ethyl 4-methylpentanoate. 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
35、-ate. Some simple examples, named both ways, are shown in the figure above,3.1 Nomenclatures of Organic Compounds,dimethyl phthalate,2019/5/7,32,If 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 cal
36、led but-2-yl propanoate or but-2-yl propionate,Esters(酯),3.1 Nomenclatures of Organic Compounds,propionic acid - 丙酸,2019/5/7,33,2,2,2-trifluoroethanoic acid,1,2-ethanedioic acid (oxalic acid 草酸),Isopropyl 2,2-dimethylbutanoate,Check8: Please give name to the following structures,2019/5/7,34,.,8. Ami
37、nes(胺),3.1 Nomenclatures of Organic Compounds,2-butanamine,cyclohexanamine,Primary Amines (伯胺，R-NH2) are named for the attached alkane chain with the suffix “-amine” (e.g. CH3NH2 methanamine). If necessary, the bonding position infixed,If higher precedence functional groups are present (see order of
38、 precedence, below), the prefix “amino“ is used with the bonding position,2019/5/7,35,diethylamine,For secondary amines (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
39、 prefix given as an italic （斜体的） N : CH3NHCH2CH3 is N-methylethanamine.,乙二胺,N-甲基乙胺,N-甲基-N-乙基丙胺,N-ethylethanamine,2019/5/7,36,trimethylamine,triphenylamine,Tertiary amines (叔胺，R-NR-R) are treated similarly: CH3CH2N(CH3)CH2CH2CH3 is N-ethyl-N-methylpropanamine. Again, the substituent groups are ordere
40、d alphabetically.,三甲胺,三苯胺,2019/5/7,37,N-methylpropan-1-amine,N-ethyl-N-methylbutan-1-amine,N,N-dimethylbutan-2-amine,Check 9: Please give name to the following structures,2019/5/7,38,Amides (R-CO-NH2) take the suffix “-amide“. There is no prefix form, and no location number is required since they al
41、ways terminate a carbon chain, e.g. CH3CONH2 (acetamide) is named 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(
42、酰胺),3.1 Nomenclatures of Organic Compounds,2019/5/7,39,N-methylpropanamide,N,N-dimethylpropanamide,N-isopropyl-N-methylbut-2-en-amide,Check 10: Please give name to the following structures,2019/5/7,40,Benzene is the most common aromatic parent structure. a. The benzene ring is named as a phenyl grou
43、p when it is a substituent.b. Multiple substituents on a benzene ring 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 placemen
44、t) or para (p-) (1-4 placement).,ortho-xylene,10. Aromatic hydrocarbon(芳香烃）,Phenylethyne,benzene,meta-xylene,para-xylene,2019/5/7,41,Select the names for each structure:1. Chlorocyclohexane2. Chlorobenzene3. 1-chlorobenzene1. Meta-methyltoluene2. Meta-dimethylbenzene3. 1,3-dimethylbenzene,Check 11:
45、Please give name to the following structures,2019/5/7,42,1,3-diethyl-2-methylbenzene,1,3-dichlorobenzene,Ortho-chlorotoluene,1-ethyl-2-methylbenzene,1-methyl-3-vinyl - benzene,vinyl ：乙烯基,2019/5/7,43,anthracene,phenanthrene,a -isopropylnaphthalene,1-ethyl-5-methylnaphthalene,1-methylnaphthalene -meth
46、ylnaphthalene,2-ethenylnaphthalene -vinylnaphthalene,naphthalene,2019/5/7,44,nitro: 硝基,2019/5/7,45,When compounds contain more than one functional group, the order of precedence determines which groups are named with prefix or suffix forms. The highest precedence group takes the suffix, with all oth
47、ers taking the prefix form. However, double and triple bonds only take suffix form (-ene and -yne) and are used with other suffixes.Prefixed substituents are ordered alphabetically (excluding any modifiers such as di-, tri-, etc.), e.g. chlorofluoromethane, not fluorochloromethane. If there are mult
48、iple functional groups of the same type, either prefixed or suffixed, the position numbers are ordered numerically (thus ethane-1,2-diol, not ethane-2,1-diol.) The N position indicator for amines and amides comes before “1“, e.g. CH3CH(CH3)CH2NH(CH3) is N,2-dimethylpropanamine.,Order of precedence o
49、f groups,3.1 Nomenclatures of Organic Compounds,Carboxylic acid amide ester aldehyde ketone alcohol amine alkyne=alkene alkane,2019/5/7,46,Order of Precedence Among Common Functional Groups,2019/5/7,47,1-Aminocyclopentane-1-carboxylic acid,2-amino-3-buten-1-ol,Please give name to the following struc
50、tures,2019/5/7,48,1,3-dihydroxypent-4-yn-2-one,4-oxohexanoic acid,2-amino-3-hydroxy-5-oxo-8-phenyloct-2-en-6-ynoic acid,2019/5/7,49,2.2 Nomenclature of inorganic chemistry,2019/5/7,50,3.2 Nomenclature of inorganic chemistry,2019/5/7,51,Outline,Elements Naming Metal Oxides. Bases, and Salts Acids Nonmetal oxides Nonmetal hydrides,
