[理学]chapter 11醇、醚

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1、Chapt11AlcoholsandEthers醇、醚的命名醇的制备——羟汞化－还原反应——硼氢化－氧化反应醇的化学反应醚的制备醚的化学反应——保护基环氧化合物StructureandNomencaltureAlcohols:-OHisattachedtoasaturatedcarbonatom.Enols:-OHisattachedtoanunsaturatedcarbonatom.CH3CH2OHEthanolH–C≡CCH2OH2-PropynolCH2=CHCH2OH2-PropenolBenzylalcoholPheno

2、ls:-OHisattachedtoabenzenering.Ethersarecompoundswhosemoleculeshaveanoxygenatombondedtotwocarbonatom.Phenolp-Methylphenol(p-Cresol)CH2=CHCH2–O–CH3Allylmethylether烯丙基NomenclatureofEthersIUPACsubstitutivenamesareusedformorecomplicatedethersandforcompoundswithmorethanone

3、etherlinkage.Ethersarenamedasalkoxyalkanes,alkoxyalkenes,andalkoxyarenes.Simpleethersarefrequentlygivencommonradicofunctionalnames.Methylphenylether(Anisole茴香醚，苯甲醚)1,2-DimethoxyethaneCH3–O–CH2CH2–O–CH32-Methoxypentane1-Ethoxy-4-methylbenzeneCyclicetherscanbenamesinsev

4、eralways.Replacementnomenclature:relatingthecyclicethertothecorrespondinghydrocarbonringsystemandusetheprefixoxa-toindicatethatanoxygenatomreplacesaCH2group.Oxirane:acyclicthree-memberedether(epoxide).Oxetane:acyclicfour-memberedether.Commonnames:giveninparentheses.Ox

5、acyclopropaneoroxirane(ethyleneoxide)1,4-Dioxacyclohexane(1,4-dioxane)OxacyclobutaneoroxetaneOxacyclopentane(tertahydrofuran)PhysicalPropertiesofAlcoholsAlcoholshavemuchhigherb.p.thancomparableethersorhydrocarbons.------H-bondMethanol,ethanol,bothpropanols,andtert-but

6、ylalcoholarecompletelymisciblewithwater.95%ethanoland5%waterazeotrope(共沸物,78.15°C)Thesolubilityofalcoholsinwatergraduallydecreasesasthehydrocarbonportionofthemoleculelengthens.PhysicalPropertiesEthersEthershavesimilarboilingpointsthatarecomparablewiththoseofhydrocarb

7、onsofthesamemolecularweight.-----Theb.p.ofdiethylether(MW=74)is34.60C;thatofpentane(MW=74)is360C.Ethersareabletoformhydrogenbondswithcompoundssuchaswater.Ethershavesolubilitiesinwaterthataresimilartothoseofalcoholsofthesamemolecularweight.-----Diethyletherand1-butanol

8、havethesamesolubilityinwater,approximately8g/100mLatroomtemperature.Pentane,bycontrast,isvirtuallyinsolubleinwater.Synthesis