Ch.26 – Organic Chemistry – Nomenclature

2-chloroethanol 2- 氯 乙 醇 A. Introduction引言 The name of an organic compound comprises three parts: 有機化合物的名稱由三部分組成： e.g. Cl - CH2CH2 – OH 2-chloroethanol 2- 氯 乙 醇 Prefix - indicating substituent groups 詞頭 -顯示取代基 2. Stem - indicating parent hydrocarbon 主幹 - 顯示母烴主鏈 3. Suffix - indicating the principal functional groups 詞尾- 顯示主要官能基

B. Nomenclature of hydrocarbons烴的命名 Straight chain acyclic hydrocarbons 直鏈無環烴

CH3CH2CH2CH2CH2CH2CH2CH3 CH3CH2CH3 Octane 辛烷 Propane 丙烷 CH≡CH CH3CH＝CH2 ethyne 乙炔 Propene 丙烯

CH3CH2CH＝CHCH＝CH2 CH3CH＝CHCH3 Hexa-1,3-diene 己-1,3-二烯 But-2-ene 丁-2-烯 CH2＝CHOH Ethenol 乙烯醇

b) Branched-chain acyclic hydrocarbons 支鏈無環烴   2-methylhexane 2-甲基己烷 3-methylheptane 3-甲基庚烷

3-methylbut-1-ene 3-甲基丁-1-烯     5-methylhex-1-yne 5-甲基己-1-炔

4-ethyl-2-methylhexane 4-乙基-2-甲基己烷   3-ethyl-3-methylhexane 3-乙基-3-甲基己烷

2,3-dimethylbutane 2,3-二甲基丁烷   2,3,4-trimethylpentane 2,3,4-三甲基戊烷

2,2,4,4-tetramethylpentane 2,2,4,4-四甲基戊烷

c) Cyclic hydrocarbons環烴     cyclohexane 環己烷 cyclopentadiene 環戊二烯 cyclohexa-1,4-diene 環己-1,4-二烯 cyclohexa-1,3-diene 環己-1,3-二烯

d) Aromatic hydrocarbons芳香烴 anthracene benzene苯 naphthalene 

      1,2,3-trimethylbenzene 1,2,3-三甲基苯 1-ethyl-4-methylbenzene 1-乙基-4-甲基苯

Ex. 1. Give the structural formula for each of the following compounds: (a) 2-methylbutane (b) 2,2,3-trimethylpentane (c) 3-ethyl-2-methylhexane (d) 3-methylbut-1-ene (e) 2-propylpent-1-ene (f) 3-ethylhex-1-yne (g) 1,2-dimethylbenzene (h) cyclopentane

Ex. 1. Give the structural formula for each of the following compounds: (a) 2-methylbutane (b) 2,2,3-trimethylpentane (c) 3-ethyl-2-methylhexane (d) 3-methylbut-1-ene (e) 2-propylpent-1-ene (f) 3-ethylhex-1-yne (g) 1,2-dimethylbenzene (h) cyclopentane

Ex. 1. Give the structural formula for each of the following compounds: (a) 2-methylbutane (b) 2,2,3-trimethylpentane (c) 3-ethyl-2-methylhexane (d) 3-methylbut-1-ene (e) 2-propylpent-1-ene (f) 3-ethylhex-1-yne (g) 1,2-dimethylbenzene (h) cyclopentane

Ex. 1. Give the structural formula for each of the following compounds: (a) 2-methylbutane (b) 2,2,3-trimethylpentane (c) 3-ethyl-2-methylhexane (d) 3-methylbut-1-ene (e) 2-propylpent-1-ene (f) 3-ethylhex-1-yne (g) 1,2-dimethylbenzene (h) cyclopentane

2.Give the IUPAC name for each of the following compounds: 2,4-Dimethylhex-2-ene 2,4-二甲基己-2-烯 Dimethylpropane 二甲基丙烷 3-Methylpent-1-yne 3-甲基戊-1-炔 1-Methylcyclohexene 1-甲基環己烯 Ethylbenzene 乙基苯

C. Derivatives of hydrocarbons烴的衍生物 Compounds with functional groups that must be designated as prefixes a) 化合物含只能作詞頭的官能基：

methoxyethane 甲氧基乙烷 3-bromohexane 3-溴己烷 Chlorocyclohexane 氯環己烷 2-chloro-3-methylpentane 2-氯-3-甲基戊烷

3-iodo-1-methoxybutane 3-碘-1-甲氧基丁烷 1,1,1-trichloroethane 1,1,1-三氯乙烷 1,2-dimethoxyethane 1,2-二甲氧基乙烷 1,3-dinitrocyclobutane 1,3-二硝基環丁烷

b) Compounds with functional groups that must be designated as prefixes or suffixes 化合物含可作詞頭或詞尾的官能基： Only one type of functional group: 只含一種官能基：

Alcohols (ending ‘-ol’) 烷醇 (以 ‘醇’ 結尾) butan-2-ol 丁-2-醇 propan-1-ol 丙-1-醇

3-chloropropan-1-ol 3-氯丙-1-醇 4 -methylpentan-1-ol 4-甲基戊-1-醇 4,4 -dimethylpentan-2-ol 4,4 -二甲基戊-2-醇

2. Aldehydes (ending ‘-al’) and ketones (ending ‘-one’) 烷醛 (以 ‘醛’ 結尾) 及烷酮 (以 ‘酮’ 結尾)   3-methylpentanal 3-甲基戊醛 Ethanal 乙醛 4-chlorobutanal 4-氯丁醛

    butanone 丁酮 2-methylpentan-3-one 2-甲基戊-3-酮

3. Carboxylic acids (ending ‘-oic acid’) 羧酸 (以 ‘酸’ 結尾)     4-methylhexanoic acid 4-甲基己酸 Propanoic acid 丙酸

4. Acyl chlorides (ending ‘-yl chloride’) 氯(以 ‘氯’ 結尾)     Ethanoyl chloride 乙氯 butanoyl chloride 丁氯

5. Amides (ending ‘amide’) 胺(以 ‘胺’ 結尾)     N-ethylbutanamide N-乙基丁胺 Propanamide 丙胺 N,N-dimethylpropanamide N,N-二甲基丙胺

6. Esters (ending ‘-oate’) 酯(以 ‘酯’ 結尾)   Methyl ethanoate 乙酸甲酯 ethyl 2-methylbutanoate 2-甲基丁酸乙酯 Ethenyl ethanoate 乙酸乙烯酯

Give the structural formula for each of the following compounds: (a) 2-methylhexane (b) 4-methylheptan-2-ol (c) pentan-2-one (d) 5-methylhexanoic acid (e) methyl 2,2-dimethylpentanoate (f) N-ethyl-N-propylethanamide

Solution: (a) (b) (c) (d)

Solution: (e) (f)

2. Give the IUPAC name for each of the following compounds: Pentan-2-ol 戊-2-醇 3,4-Dimethylpentanoic acid 3,4-二甲基戊酸 N,N-Dimethylpropanamide N,N-二甲基丙胺 3,4-Dimethylhexanal 3,4-二甲基己醛

(II) Two types of functional groups

4-chloro-4-methylpentanal 4-氯-4-甲基戊醛 2-bromo-3-methylbut-2-enoic acid 2-溴-3-甲基丁-2-烯酸 3-chloro-2-iodobutanamide 3-氯-2-碘丁胺

3,4-dichloro-5-hydroxy-4-methylpentan-2-one 3,4-二氯-5-羥基-4-甲基戊-2-酮 4-amino-2-phenylhexanal 4-氨基-2-苯基己醛

Ex. 1. Give the structural formula for each of the following compounds: (a) 3-oxobutanoic acid (b) 5-hydroxypentanal (c) 2-hydroxy-4-oxohexanal (d) 1,8-dihydroxyoctan-3-one

2. A student has given the wrong names for the following organic compounds. Given the structural formulae and the correct names for these compounds. (a) 3-hydroxy-3-ethylbutanoic acid (b) 2-chloro-3-cyano-1-methylpropane (c) propoxyethane 3-Hydroxy-3-methylpentanoic acid 3-羥基-3-甲基戊酸

2. A student has given the wrong names for the following organic compounds. Given the structural formulae and the correct names for these compounds. (a) 3-hydroxy-3-ethylbutanoic acid (b) 2-chloro-3-cyano-1-methylpropane (c) propoxyethane 3-Chloropentanenitrile 3-氯戊

2. A student has given the wrong names for the following organic compounds. Given the structural formulae and the correct names for these compounds. (a) 3-hydroxy-3-ethylbutanoic acid (b) 2-chloro-3-cyano-1-methylpropane (c) propoxyethane Ethoxypropane 乙氧基丙烷

Give the IUPAC name for each of the following compounds: (a) (b) (c) (d) 3-Chlorobutanone 3-氯丁酮 1-Ethoxyethanol 1-乙氧基乙醇 2-Amino-3-hydroxypentanoic acid 2-氨基-3-羥基戊酸 4-Hydroxy-2-methylpentanamide 4-羥基-2-甲基胺

D. Derivatives of aromatic hydrocarbons 芳香烴的衍生物 Monosubstituted aromatic hydrocarbons 單取代芳香烴 fluorobenzene 氟苯 chlorobenzene 氯苯 bromobenzene 溴苯 nitrobenzene 硝基苯

phenol 酚 aniline 苯胺 benzenesulphonic acid 苯磺酸 toluene 甲苯

benzoic acid苯酸 benzaldehyde 苯醛 acetophenone 苯乙酮 benzonitrile 苯甲

b) Polysubstituted aromatic hydrocarbons 多取代芳香烴 1,2-dibromobenzene 1,2-二溴苯 1,3-dichlorobenzene 1,3-二氯苯 1,4-dinitrobenzene 1,4-二硝基苯

1-bormo-2-chlorobenzene 1-溴-2-氯苯 2-bromo-1-chloro-4-nitrobenzene 2-溴-1-氯-4-硝基苯

3,5-dinitrobenzoic acid 3,5-二硝基苯酸 2,4-dichlorophenol 2,4-二氯酚

Ex.1. Give the structural formula for each of the following compounds: (a) 1,4-dichlorobenzene (b) 3-nitrobenzoic acid (c) 4-bromotoluene (d) 3,5-dinitrophenol

Give the IUPAC name for each of the following compounds: 5-Bromo-2-chlorobenzoic acid 5-溴-2-氯苯酸 2-Bromo-1,4-dichlorobenzene 2-溴-1,4-二氯苯 2,4-Difluorobenzenesulphonic acid 2,4-二氟苯磺酸 4-Hydroxybenzoic acid 4-羥基苯酸