Nomenclature_of_Organic_Compounds.ppt

1、Nomenclature of Organic Compounds,The field of organic chemistry is vast, for it includes not only the composition of all living organisms but also of a great many other materials that we use daily. It is physically impossible for one to study the properties of each of the hundreds of thousands of k

2、nown organic compounds.,The Need for Classification of Organic Compounds,Hence organic compounds with similar structural features are grouped into series or classes. Some of the classes of organic compounds are hydrocarbons, alcohols, aldehydes, ketones, ethers, carboxylic acids, esters, carbohydrat

3、es, and proteins. Each of these classes of compounds is identified by certain characteristic structural features.,Classes,hydrocarbons, 烃类，碳氢化合物 alcohols, 醇类 aldehydes, 醛类 ketones, 酮类 ethers, 醚类 carboxylic acids, 羧酸 esters, 酯类 carbohydrates,糖类，碳水化合物,IUPAC System,Beginning with a meeting in Geneva in

4、 1892, an international system for naming compounds was developed. In its present form, the system recommended by the International Union of Pure and Applied Chemistry is systematic, generally unambiguous, and internationally accepted. It is called the IUPAC System.,Geneva dini:v 日内瓦 IUPAC 国际纯粹与应用化学

5、联合会,IUPAC System,Despite the existence of the official IUPAC System, a great many well-established common or trivial names, and even abbreviations are used , and because of their brevity and convenience, will doubtless continue to be used. So it is necessary to have a knowledge of both the IUPAC Sys

6、tem and of many non-IUPAC common names.,Hydrocarbon,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 alkanes, alkenes, alkynes, and aromatic hydrocarbons.,alkanes, lkeinz 烷烃 alkenes, lk

7、i:nz 烯烃 alkynes, lkainz 炔烃 aromatic hydrocarbons，芳香烃,Hydrocarbon,The alkanes, also known as “paraffins” or “saturated hydrocarbons”, are straight or branched-chain hydrocarbons having only single covalent bonds between the carbon atoms. It is necessary to learn the names of the first 10 members of t

8、he alkane series as these names are used, with slight modifications, for corresponding compounds belonging to other classes.,Rule A-1. Saturated Unbranched-chain Compounds and Univalent Radicals Rule A-2. Saturated Branched-chain Compounds and Univalent Radicals Rule A-3. Unsaturated Compounds and U

9、nivalent Radicals,Rule A-1.Saturated Unbranched-chain Compounds and Univalent Radicals,二 有机物的命名,1 烷烃（alkanes） 1.1 直链烷烃 烃类化合物的命名是有机命名的基础。英文名称除了含1到4个碳原子以外，其余均用希腊文和拉丁文的数词加上相应的词尾（-ane）来命名，10个碳原子以上的则在数词前加前缀un、do、tri、tetra、penta等。 Alkane = Number prefix-ane,Rules,1119Alkane = Number prefix-decane 2129Alka

10、ne = Number prefix-cosane 3139Alkane = Number prefix-triacontane 4090Alkane = Number prefix-contane,1119Alkane = Number prefix-decane,11 Undecane 12 Dodecane 13 Tridecane 14 Tetradecane 15 Pentadecane,16Hexadecane 17 Heptadecane 18 Octadecane 19 Nonadecane,Examples 1-1,20Icosane 21 Henicosane 22 Doc

11、osane 23 Tricosane 24 Tetracosane,Examples 1-2,25 Pentacosane 26 Hexacosane 27 Heptacosane 28 Octacosane 29 Nonacosane,2129Alkane = Number prefix-cosane,Examples 1-3,30 Triacontane 31 Hentriacontane 32 Dotriacontane 33 Tritriacontane 34 Tetratriacontane,3139Alkane = Number prefix-triacontane,35 pent

12、atriacontane 36 Hexatriacontane 37 Heptatriacontane 38 Octatriacontane 39 Nonatriacontane,Examples 1-4,20Icosane 30 Triacontane 40 Tetracontane 50 Pentacontane,2090Alkane = Number prefix-contane,60 Hexacontane 70 Heptacontane 80 Octacontane 90 Nonacontane,132 Dotriacontahectane,100 Hectane 32 Dotria

13、contane,Univalent radicals,命名烷基时，只需把“基”（-yl）字加在相应的烷烃的字首后。 Radical = Alk -yl for example: CH3- Methyl CH3CH2- Ethyl CH3CH2CH2- Propyl CH3(CH2)2CH2- Butyl,Examples-2,5 Pentane,11 Undecane,Questions A-1-1,1. Give the name of the alkane represented by each of the following line structures:,Undecane Buta

14、ne Octane 3 Propane,Questions A-1-2,2. Give the name and the line structure for the unbranched alkane with the following formulas: C6H14 C9H20 C2H6 C8H18 CH4 C4H10 C10H22,6 Hexane 2 Ethane 10 Decane 9 Nonane 8 Octane 4 Butane 1 Methane,Rule A-2. Saturated Branched-chain Compounds and Univalent Radic

15、als,2.1 支链烷烃和烷基,Univalent radicals derived from saturated unbranched acyclic hydrocarbons by removal of hydrogen from a terminal carbon atom are named by replacing the ending -ane of the name of the hydrocarbon by -yl. 命名含支链的烷烃时，可把它们视为直链烷烃，但分別是某些氢（hydrogen）原子被称为烷基的原子取代。命名烷基时，只需把“基”（-yl）字加在相应的烷烃的字首后。

16、,A saturated branched acyclic hydrocarbon is named by prefixing the designations of the side chains to the name of the longest chain present in the formula,Methane Methyl 5 Pentane,The following names are retained for unsubstituted hydrocarbons only:,methyl propane,methyl butane,Saturated branched-c

17、hain hydrocarbon,branched-chain hydrocarbon = N - Radical+alkane for example:,Questions A-2-1,Answers A-2-1,对取代的烷基也可以在相应的烃名前加“异”（iso-）、“仲”(sec-)、 “叔”（tert-）、“新”（neo-）等字命名。,2.2 可采用普通命名的支链烷烃：,Isobutane Isopentane,methyl propane,methyl butane,Neopentane Isohexane,2,2-dimethyl propane,2,2-dimethyl propa

18、ne,下面是一些符合条件的烷基，其系统命名和普通命名如下： Isopropyl 1-Methylethyl Isobutyl 2-Methylpropyl sec-Butyl 1-Methylpropyl,tert-Butyl 1,1-Dimethylethyl Isopentyl 3-methybutyl Neopentyl 2,2-Dimethylpropyl,tert-Pentyl 1,1-Dimethylpropyl Isohexyl,Questions A-2-2,Answers A-2-2,2.3 复杂的烷烃 结构较复杂的烷烃不能用普通命名法命名，只能采用系统命名法。选最长的碳链为

19、主链，从一端向另一端编号，支链作为取代基放在母体名称前，编号时使支链的编号尽可能小且支链的排列按基团的字母顺序。 如: 3-Ethyl-2-methylhexane 4-ethyl-3,3-dimethylheptane,烷烃的命名规则,（1）选最长碳链作母体 （2）侧链作为烷基 （3）序号最小 （4）选取代基多 （5）侧链作前缀 a:烷基字头字母顺序 b:先简后繁,The longest chain is numbered from one end to the other by Arabic numerals, the direction being so chosen as to giv

20、e the lowest numbers possible to the side chains. When series of locants containing the same number of terms are compared term by term, that series is lowest which contains the lowest number on the occasion of the first difference. This principle is applied irrespective of the nature of the substitu

21、ents,Examples,Polyside chain hydrocarbon,ButylEthylIsopropylMethylPropyl for example:,Univalent branched radicals,Radical = Alk -yl for example:,Questions A-2-3,Answers A-2-3,Rule A-3. Unsaturated Compounds and Univalent Radicals,3.1,Unsaturated unbranched acyclic hydrocarbons having one double bond

22、 are named by replacing the ending -ane of the name of the corresponding saturated hydrocarbon with the ending -ene. If there are two or more double bonds, the ending will be -adiene, -atriene, etc. The generic names of these hydrocarbons (branched or unbranched) are alkene, alkadiene, alkatriene, e

23、tc.,命名 烯烃命名时将相应的烷烃的词尾“烷”（ane）改为“烯”（ene），名称前加上不饱和键的编号即可。当所带的双键或叁键不止一个时，可在前边加上di、tri、tetra等数字来表示。例如： CH2=CH2 Ethene CH2=CHCH2CH2CH3 1-Pentene CH2=C=CH2 1,2-Propadiene,For example,2- Hexene 1,4-Hexadiene,Unbranched acyclic alkene,Alkene = Number prefix-ene for example: C-C-C-C=C-C 2-Hexene C-C=C Propen

24、e C-C=C-C 2-Butene C-C-C-C=C 1-Pentene,Poly-ene,n-Alkene =Alk-a-n-ene n=2 -adiene n=3 -atriene n=4 -atetraene for example: C-C=C-C=C-C=C 1,3,5-Heptatriene C=C-C=C 1,3-Butadiene C-C=C-C=C 1,3-Pentadiene,含支链烯烃的命名规则,含双键最长链 母体将相应烷的词尾-ane改为烯的词尾-ene 双键以最小序号 余同烷烃,3.2,Unsaturated unbranched acyclic hydrocar

25、bons having one triple bond are named by replacing the ending -ane of the name of the corresponding saturated hydrocarbon with the ending -yne. If there are two or more triple bonds, the ending will be -adiyne, atriyne, etc. The generic names of these hydrocarbons (branched or unbranched) are alkyne

26、, alkadiyne, alkatriyne, etc.,Alkyne,Alkyne = Alk-yne (-a-n-yne) n=2 -adiyne n=3 -atriyne for exanmple:,Questions A-3-2,2-Methyl-3-octyne,2,5-Dimethyl-3-hexyne,4-Butyl-4-propyl-2-decyne,Questions A-3-2,3-Propyl-1,6-heptdiyne 4,4-Dimethyl-2,5-heptdiyne,3.3,Unsaturated unbranched acyclic hydrocarbons

27、having both double and triple bonds are named by replacing the ending -ane of the name of the corresponding saturated hydrocarbon with the ending -enyne, -adienyne, -atrienyne, -enediyne, etc.,烯炔的命名,烃类分子中同时含有双键和叁键时成为烯炔，命名时烯在前炔在后，双键的编号写在前面，叁键的定位号写在表示炔烃词尾之前。例如： 1,3-Hexadien-5-yne 3-Penten-1-yne,Unsatu

28、rated hydrocarbon withboth double and triple bonds,Alkenyne = Number prefix-en-yne Two ene + one yne -adien-?-yne Three ene+ one yne -atrien-?-yne One ene + two yne -en-?-diyne for example:,Numbers as low as possible are given to double and triple bonds even though this may at times give -yne a lowe

29、r number than -ene. When there is a choice in numbering, the double bonds are given the lowest numbers.,Examples 3.3,Practices 3.3,1,3-Hexadien-5-yne 3-Penten-1-yne 1-Penten-4-yne,系统命名中，应选含不饱和键最多且最长的直链。如分子中有两条直链具有相同数目的不饱和键时，取碳原子数较多者为主链。如碳原子数相同，则取含双键数目较多者为主链。例如: 3,4-Dipropyl-1,3-hexadien-5-yne,4-Vinyl-1-hepte