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Chapter16
Ethers,Epoxides,andSulfides
16.1
NomenclatureofEthers,Epoxides,andSulfides
nameasalkoxyderivativesofalkanesCH3OCH2CH3methoxyethaneCH3CH2OCH2CH3ethoxyethaneCH3CH2OCH2CH2CH2Cl1-chloro-3-ethoxypropaneSubstitutiveIUPACNamesofEthers
namethegroupsattachedtooxygenin
alphabeticalorderasseparatewords;etheris
lastwordCH3OCH2CH3ethylmethyletherCH3CH2OCH2CH3diethyletherCH3CH2OCH2CH2CH2Cl3-chloropropylethyletherFunctionalClassIUPACNamesofEthers
nameasalkylthioderivativesofalkanesCH3SCH2CH3methylthioethaneCH3CH2SCH2CH3ethylthioethane(methylthio)cyclopentaneSubstitutiveIUPACNamesofEthersSCH3
cyclopentylmethylsulfideanalogoustoethers,butreplace“ether”aslast
wordinthenameby“sulfide.”CH3SCH2CH3ethylmethylsulfideCH3CH2SCH2CH3diethylsulfideFunctionalClassIUPACNamesofSulfidesSCH3
Oxirane
(Ethyleneoxide)OxetaneOxolane
(tetrahydrofuran)Oxane
(tetrahydropyran)1,4-Dioxane
NamesofCyclicEthersOOOOOO
ThiiraneThietaneThiolaneThianeNamesofCyclicSulfidesSSSS
bentgeometryatoxygenanalogous
towaterandalcohols16.2
StructureandBonding
in
EthersandEpoxides
112°HOH105°108.5°(CH3)3COC(CH3)3132°HOCH3CH3OCH3Bondanglesatoxygenaresensitive
tostericeffects
moststableconformationofdiethylether
resemblespentaneAnoxygenatomaffectsgeometryinmuchthe
samewayasaCH2group
moststableconformationoftetrahydropyran
resemblescyclohexaneAnoxygenatomaffectsgeometryinmuchthe
samewayasaCH2group
16.3
PhysicalPropertiesofEthers
boilingpoint36°C35°C117°CEthersresemblealkanesmorethanalcohols
withrespecttoboilingpointOOH Intermolecularhydrogen
bondingpossiblein
alcohols;notpossible
inalkanesorethers.
solubilityinwater(g/100mL)verysmall97.5Ethersresemblealcoholsmorethanalkanes
withrespecttosolubilityinwaterOOH Hydrogenbondingto
waterpossibleforethers
andalcohols;not
possibleforalkanes.
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