厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十一章 醇和醚（11.1-11.3）Structure and Nomenclaturechpt11_1

Chapter 11 Alcohols and Ethers 醇和两

Chapter 11 Alcohols and Ethers 醇和醚

ORGANIC CHEMISTRY Chapter ll 11.1 Structure and Nomenclature Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.1 Structure and Nomenclature

ORGANIC CHEMISTRY Chapter ll o Alcohols are compounds whose molecules have a hydroxyl group attached to a saturated carbon atom CH3OH CH3 CH,OH CH3 CHCH3 CH3)3COH OH Methanol Ethanol 2-Propanol 2-Methyl-2-Propanol a1° alcohol a2° alcohol a3° alohol CH2OH CH,=CHCH,OH HC=CCH,OH Benzyl alcohol 2-Propenol 2-Propynol Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 Alcohols are compounds whose molecules have a hydroxyl group attached to a saturated carbon atom. CH3OH CH3CH2OH CH3CHCH3 OH (CH3)3COH Methanol Ethanol 2-Propanol 2-Methyl-2-Propanol a 1° alcohol a 2° alcohol a 3° alohol CH2OH CH2 CHCH2OH HC CCH2OH Benzyl alcohol 2-Propenol 2-Propynol

ORGANIC CHEMISTRY Chapter ll o Compounds that have a hydroxyl group attached directly to an aromatic ring are called heno o Compounds in which a hydroxyl group is attached to a vinylic carbon are called enolS OH OH C=C CH3 Phenol p- Methylphenol an enol(烯醇) Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 Compounds that have a hydroxyl group attached directly to an aromatic ring are called phenols. Compounds in which a hydroxyl group is attached to a vinylic carbon are called enols OH C C OH (烯醇) OH CH3 Phenol p-Methylphenol an enol

ORGANIC CHEMISTRY Chapter ll o Ethers differ from alcohols in that the oxygen atom of an ether is bonded to two carbon atoms The hydrocarbon groups may be alkyl, alkenyl (烯基), vinyl(乙烯基, alkynyl(炔基), or aryl (芳基 CHrCH,-O-CH,CH O-CH3 CH2,O-CH=CH Methyl phenyl ether Ethyl vinyl ether D ethyl ether (Anisole 二乙醚(乙醚)苯甲醚茴香醚) 乙基乙烯基醚 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 Ethers differ from alcohols in that the oxygen atom of an ether is bonded to two carbon atoms. The hydrocarbon groups may be alkyl, alkenyl (烯基), vinyl (乙烯基), alkynyl (炔基), or aryl (芳基). O CH3 苯甲醚(茴香醚) Methyl phenyl ether CH3CH2 O CH 乙基乙烯基醚 Ethyl vinyl ether CH3CH2 O CH2CH3 二乙醚(乙醚) Diethyl ether (Anisole) CH2

ORGANIC CHEMISTRY Chapter ll 11.a Nomenclature of alcohols o Simple alcohols are name by the IUPac system as derivatives of the parent alkane, using the suffix -ol H OH CH CHCHCH OH OH 顺-1.4-环己二醇 3-苯基-2-丁醇 cis-1 4-Cyclohexanediol 3-Pheny1-2-butanol CH,CI 2-(氯甲基)-1-丁醇 CH3 CH, CHCH,OH 2-(Chloromethyl)-1-butanol) Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.1A Nomenclature of Alcohols Simple alcohols are name by the IUPAC system as derivatives of the parent alkane, using the suffix -ol H H OH OH CHCHCH3 CH3 OH CH3CH2CHCH2OH CH2Cl 顺-1,4-环己二醇 cis-1,4-Cyclohexanediol 3-苯基-2-丁醇 2- (氯甲基)-1-丁醇 3-Phenyl-2-butanol 2-(Chloromethyl)-1-butanol)

ORGANIC CHEMISTRY Chapter ll o Certain simple and widely occurring alcohols have common names that are accepted by iupac, for example (CH3 )3 COH CH -CHCH,OH CH2OH tert-Butyl alcohol Allyl alcohol Benzyl alcohol (2-Methyl-2-propanol)(2-Propen-1-ol)(Phenylmethanol 叔丁醇 烯丙醇 苄醇 H HOCH, CH,OI CHCHCH2 OH OHOH Ethylene glycol Glycerol (1, 2-Ethanediol 1, 2, 3-Propanetriol) 乙二醇 甘油 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 Certain simple and widely occurring alcohols have common names that are accepted by IUPAC, for example: CH2 CHCH2OH CH2OH 烯丙醇 苄醇 Allyl alcohol Benzyl alcohol (2-Propen-1-ol) (Phenylmethanol) HOCH2CH2OH CH2CHCH2 OH OHOH 乙二醇 甘油 Ethylene glycol Glycerol (1,2-Ethanediol) (1,2,3-Propanetriol) 叔丁醇 (2-Methyl-2-propanol) tert-Butyl alcohol (CH3)3COH

ORGANIC CHEMISTRY Chapter ll 11.1B Nomenclature of ethers o Common names-two alkyl groups(in alphabetical order)+ ether o IUPAC nomenclature -ethers are named as alkoxy(RO-烷氧基) derivatives of alkanes CH3-o-CH2CH3 CH3 CH2-O-CH2CH3 CH3 -0-C(CH3)3 Ethyl methyl ether Diethyl ether tert-Buthyl methyl ether 甲基乙基醚 二乙醚(乙醚) 甲基叔丁基醚 Methoxyethane Ethoxyethane 2-Methyl-2-methoxypropane Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 11.1B Nomenclature of Ethers Common names — two alkyl groups (in alphabetical order) + ether IUPAC nomenclature — ethers are named as alkoxy (RO– 烷氧基) derivatives of alkanes CH3CH2 O CH2CH3 二乙醚(乙醚) Diethyl ether CH3 O CH2CH3 CH3 O C(CH3)3 甲基乙基醚 甲基叔丁基醚 Ethyl methyl ether tert-Buthyl methyl ether Methoxyethane Ethoxyethane 2-Methyl-2-methoxypropane

ORGANIC CHEMISTRY Chapter ll CH CH3 CH2-O-CHCH2CH2CH3 CH3 OCH2 CH2OCH 2-Ethoxypentane 1. 2-Dimethoxyethane 2-乙氧基戊烷 1.2-二甲氧基乙烷 CH2O OCH CHr CH,-O-Ch, Ch, Ch,CI 1, 4-Dimethoxybenzene 1-Chloro-3-ethoxypropane 14-二甲氧基苯 1-甲氧基-3-氯丙烷 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 CH3CH2 O CHCH2CH2CH3 CH3 2-乙氧基戊烷 2-Ethoxypentane 1,2-二甲氧基乙烷 1,2-Dimethoxyethane CH3OCH2CH2OCH3 CH3O OCH3 CH3CH2 O CH2CH2CH2Cl 1,4-二甲氧基苯 1,4-Dimethoxybenzene 1-Chloro-3-ethoxypropane 1-甲氧基-3-氯丙烷

ORGANIC CHEMISTRY Chapter ll Cyclic ethers can be named in several ways o Replacement nomenclature-oxa-to indicate that an oxygen atom replaces a CH group o Cyclic three-membered ether -oxirane o Cyclic four-membered ether -oxetane o Cyclic three-or four-membered ethers are also named by using prefix epox O O Oxacyclopentane 4-Dioxacyclohexane tetrahydrofuran,四氢呋喃)(,4- dioxane,1,4-二氧六环) Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 11 Cyclic ethers can be named in several ways: Replacement nomenclature — oxa- to indicate that an oxygen atom replaces a CH2 group. Cyclic three-membered ether — oxirane Cyclic four-membered ether — oxetane Cyclic three- or four-membered ethers are also named by using prefix epoxy￾O OO Oxacyclopentane 1,4-Dioxacyclohexane (tetrahydrofuran, 四氢呋喃) (1,4-dioxane, 1,4-二氧六环)