Survey
* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
* Your assessment is very important for improving the workof artificial intelligence, which forms the content of this project
Terms for organic chemistry 1 I. Alkanes(烷烃) Hydrocarbons having no double or triple bond functional groups are classified as alkanes or cycloalkanes, depending on whether the carbon atoms of the molecule are arranged only in chains or also in rings. Although these hydrocarbons have no functional groups, they constitute the framework on which functional groups are located in other classes of compounds, and provide an ideal starting point for studying and naming organic compounds. 2 1. Acyclic Alkanes (非环烷烃,链烷烃) 1.1 Straight-chain alkanes (直链烷烃) The first four saturated unbranched acyclic hydrocarbons are called methane, ethane, propane and butane. Names of the higher members of this series consist of a numerical term, followed by “ane” with elision of terminal “a” from the numerical term。 3 4 = Number prefix-ane CH4 Methane CH3CH2CH3 Propane CH3CH3 Ethane CH3(CH2)2CH3 Butane CH3(CH2)3CH3 Pentane CH3(CH2)4CH3 Hexane CH3(CH2)5CH3 Heptane CH3(CH2)6CH3 Octane CH3(CH2)7CH3 CH3(CH2)8CH3 Decane Nonane 5 1.2 Branched alkanes and alkyl groups The naming of branched alkanes is the same as straight chain alkanes except than one or more hydrogen atoms are substituted by alkyl groups (side chain). The branched alkane is named by prefixing the designations(名称) of the side chains to the name of the longest chain present in the formula 。 6 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". Radical = Alk -yl 7 for example: CH3Methyl CH3CH2Ethyl CH3CH2CH2Propyl CH3(CH2)2CH2Butyl pentyl (amyl), hexyl, heptyl, phenyl, benzyl, isobutyl, isopentyl, cyclopropyl, cyclohexyl 8 branched-chain hydrocarbon = n-Radical+alkane C C C C 2-Methylbutane C C C C C 2,2-Dimethylpropane C C C C C C C C 4-Ethyl-2,5-dimethylheptane C C C C 9 CH2CH3 CH3CH2CH2CHCH2CHCH2CH2CH2CH3 CH3 4-甲基-6-乙基癸烷 6-ethyl-4-methyldecane 2,7-二甲基-3-乙基-4-丙基辛烷 3-ethyl-2,7-dimethyl-4-propyloctane 10 Univalent radicals derived from saturated branched acyclic hydrocarbons are also named by replacing the ending "-ane" of the name of the hydrocarbon by "-yl". But some common names are also used, such as “异” (iso-), “仲”(sec-), “叔”(tert-), “新” (neo-),etc. 11 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。下面是一些符合条件的烷基,其系统命 名和普通命名如下: (CH3)2CH-CH2-Methylpropyl Isobutyl CH3-CH2-CH(CH3)- 1-Methylpropyl sec-Butyl (CH3)3C1,1-Dimethylethyl tert-Butyl CH3-CH2-C(CH3)2- 1,1-Dimethylpropyl tert-pentyl (CH3)3C-CH22,2-Dimethylpropyl Neopentyl 12 2.cycloalkanes 2.1Unsubstituted cycloalkanes= Cyclo+alkane Cyclopropane Cyclobutane Cyclopentane Cyclohexane Cycloheptane 13 2.2 Substituted cycloalkanes They are named in a fashion very similar to that used for naming branched alkanes. The chief difference is that the numbering starts at a substituted ring atom. 1-ethyl-3-methylcyclopentane CH2CH2CH2CH2CH3 CH2CH2 1-cyclobutylpentane 1,2-dicyclohexylethane 14 II. Alkene and alkynes Alkenes and alkynes are hydrocarbons which respectively have carbon-carbon double bond and carbon-carbon triple bond functional groups. They are named by replacing “ane” with “ene” and “yne” respectively. When there are more than one double bond or triple bond, The prefixes di, tri, tetra etc are added before “ene” or “yne” . 15 C-C-C-C=C-C C-C=C C-C=C-C C-C-C-C=C C-C=C-C=C-C=C C=C-C=C C-C=C-C=C Hex-2-ene Propene But-2-ene Pent-1-ene Hepta-1,3,5-triene Buta-1,3-diene Penta-1,3-diene 16 C C C C C C C C C C C C C C Propyne 2-Pentyne Ethyne (acetylene) 1,3-Butadiyne 17 C C C C 2-Methyl-2-butene C C C C C C 2-Methyl-2,4-hexadiene C C C C C C C C C C C C 3-Ethyl-4-Methyyl-1,5-heptadiene C C C C C C C C C 2-Methyl-2,4,6-octatriene 18 III. Aromatic hydrocarbon Aromatic compounds contain benzene. Benzene C6H6 has 6 C atoms and 6 H Atoms. The structures for benzene are also written as one formula with a circle within the ring to represent the alternating double bonds. 19 Aromatic compounds are named with benzene as the parent chain. One side group is named in front of the name benzene. CH3 methylbenzene Cl chlorobenzene 20 When two groups are attached to benzene, the ring is numbered to give these substituents the lowest possible numbers. The prefixes ortho (1,2), meta (1,3-) and para (1,4-) are also used. Cl CH3 Cl CH3 Cl 1,2-dimethylbenzene 1,3-dichlorobenzene (ortho-dimethylbenzene) (meta-dichlorobenzene) CH3 1-chloro-4-methylbenzene (para-chloromethylbenzene) 21 The compound is termed as ortho if the two substituents are on the adjacent carbon atoms. In IUPAC system to indicate these positions are 1, 2. (b) Meta. The compound is termed as meta if the two substituents are on alternate carbon atom. In IUPAC system to indicate these position are 1, 3. (c) Para. The compound is termed as para if the two substituents are present on diagonally opposite carbon atoms. In IUPAC system to indicate these positions are 1, 4.. 22 IV. Alcohols Alcohol = Alkan-ol The systematic nomenclature for alcohols adds the ending -ol to the name of the parent alkane and uses a number to identify the carbon that carries the OH group. When there are more than one hydroxy groups , the prefixes di, tri, tetra etc are added before “ol” or “yne”. In this case, the letter “e” in the original suffix “ane” should be kept, since those prefixes di, tri, tetra etc begin with a consonant. 23 24 V. phenols 25 VI. ethers Alcohols (ROH) can be thought of as derivatives of water in which one of the hydrogen atoms has been replaced by an alkyl group. If both of the hydrogen atoms are replaced by alkyl groups, we get an ether (ROR). 26 1) Ethers can be named by naming each of the two carbon groups as a separate word followed by a space and the word ether. “di” indicate two same alkyl groups Ether = R+R’+ether CH3CH2OCH3 ethylmethyl ether (CH3)2CHOCH3 Isopropyl methyl ether CH3CH2CH2OCH2CH2CH3 Dipropyl ether CH3CH2OCH2CH3 diethyl ether 27 2) Alternatively, the “R2” in the ether molecule “R1O-R2” can be taken as the parent structure, while “R1O” is taken as a substitute. RO is called “alkoxy”, such as methoxy, ethoxy, propoxy, butoxy,pentyloxy, hexyloxy,ect. CH3CH2OCH3 methoxyethane (CH3)2CHOCH3 Isopropoxypropane CH3CH2CH2OCH2CH2CH3 propoxypropane CH3CH2OCH2CH3 ethoxyethane 28 VII. Aldehydes Aldehydes are organic chemical compounds that include a -carbonyl group (i.e. an oxygen atom attached to a carbon atom by a double covalent bond) and a hydogen atom attached to the same carbon atom as is attached to the carbonyl group. Aldehydes are named by replacing “e” at the end of the corresponding alkane by a suffix “-al”. 29 Aldehyde = Alkan -al CH3 CH3CHCH2CH2CH2CHO 5-Methylhexanal CH3CH2CH2CH2CHO Pentanal OHCCH2CH2CH2CH2CHO Hexanedial 30 VII. Ketones Ketones always have two carbon atoms attached to the carbon atom of the carbonyl group, so the functional group is C-CO-C. Ketones are named by replacing “e” at the end of the corresponding alkane by a suffix “-one”. If the carbon chain is five carbon atoms or longer, indicate the position of the carbonyl group by assigning it the lowest number possible. 31 O O CH3CH2CCH3 CH2 CH CH2 C CH3 2-Butanone 4-Penten-2-one O O CH3 CH2 C CH2 C CH3 2,4-Hexanedione CH3CH2 O O CH2 CH CH C CH2 C CH3 5-Ethyl-6-heptene-2,4-dione 32 VIII. Carboxylic acid Carboxylic acids contain the -COOH group .The nomenclature for carboxylic acids requires the longest carbon chain of the molecule to be identified and the -e of alkane name to be replaced with -oic acid. Carboxylic acid = Alkan-oic acid 33 HCOOH CH3-COOH CH3CH2-COOH CH2=CH-COOH CF3-COOH HOOCCOOH HOOCCH2CH2-COOH methanoic acid ethanoic acid propanoic acid propenoic acid trifluoroethanoic acid Ethanedioic acid butanedioic acid 34 CH3CH2CH2CH2CH2COOH Hexanoic acid CH3CH=CHCH2COOH 3-Pentenoic acid CH3CH=CCH=CHCOOH 4-Ethyl-2,4-hexadienoic acid CH2CH3 HO2CCH2CH2CH2CH2CH2CO2H Heptanedioic acid 35 XI. Ester In an ester, the hydrogen in the -COOH group is replaced by an alkyl group. An ester name has two parts: the part that comes from the acid (propanoate) and the part that shows the alkyl group (methyl). Ester = Alkyl (某酯)+ alkan+oate(某酸) 36 Start by thinking about propanoic acid - a 3 carbon acid with no carbon-carbon double bonds. . The hydrogen in the -COOH group is replaced by an alkyl group - in this case, a methyl group 37 CH3COOCH3 methyl ethanoate 乙酸甲酯 CH3CH2COOC2H5 COOC4H9 ethyl propanoate 丙酸乙酯 butyl benzoate 苯甲酸丁酯 38 Excise CH3CH2CHCOOH CH3 2-methyl butanoic acid 2-甲基丁酸 CH3CH CHCH2COOH 3-pentenoic acid 3-戊烯酸 CH3CH2CHCH2CHCH3 2-ethyl-4-methylpentanedioic acid COOH COOH 2-甲基- 4-乙基戊二酸 39 Exercise CH2CH 3 4 2 5 1 CH3 CH3 6 3−(2−methylpropyl)cyclohexene或 3−isobutyl cyclohexene 40 1,3-butadiene 1,3,6-heptatriene 41 5-methyl-1,3cyclohexadiene 42 4-amino-3-isopropyl-2-hexanone 5,5-dimethyl-3-oxohexanoic acid 43 2-mercapto-4-oxo-heptanal * 44 4-amino-6-heptenoic acid ethanedioic acid * or oxalic acid 45 isopropyl benzoate 1-chloro-3ethylbenzene or m-chloroethylbenzene 46 4-hydroxybenzaldehyde or p-hydroxybenzaldehyde 47 1-chloro-2-methyl-4-propylbenzene 48 2,4,6-trimethylbenzoic acid 49 3-bromo-4-methyl-benzenesulphonic acid 50 ethyl 2,4-dimethylbenzoate 51 (R)-3,4-dihydroxy-5-((S)- 1,2-dihydroxyethyl)furan-2(5H)-one (R)-3,4-二羟基-5-((S)- 1,2-二羟乙基)呋喃-2(5H)-酮 52