Structural-determination-of-organic-compounds：有机化合物的结构测定课件

StructuralDeterminationofOrganicCompounds34.1 Introduction34.2 IsolationandPurificationofOrganicCompounds34.3 TestsforPurity34.4 QualitativeAnalysisofElementsinanOrganicCompound34.5 DeterminationofEmpiricalFormulaandMolecular FormulafromAnalyticalData34.6 StructuralInformationfromPhysicalProperties34.7 StructuralInformationfromChemicalProperties34.8 UseofInfra-redSpectrocopyintheIdentificationof FunctionalGroups34.9 UseofMassSpectratoObtainStructuralInformation34StructuralDeterminationofOrThegeneralstepstodeterminethestructureofanorganiccompoundThegeneralstepstodetermineIsolationandPurificationofOrganicCompoundsIsolationandPurificationofTechniqueAim1.FiltrationToseparateaninsolublesolidfromaliquid(slow)2.CentrifugationToseparateaninsolublesolidfromaliquid(fast)3.RecrystallizationToseparateasolidfromothersolidsbasedontheirdifferentsolubilitiesinsuitablesolvent(s)4.SolventextractionToseparateacomponentfromamixturewithasuitablesolvent5.DistillationToseparatealiquidfromasolutioncontainingnon-volatilesolutesTechniqueAim1.FiltrationToseTechniqueAim6.FractionaldistillationToseparatemiscibleliquidswithwidelydifferentboilingpoints7.SteamdistillationToseparateliquidswhichareimmisciblewithwateranddecomposeeasilybelowtheirb.p.8.Vacuumdistillationditto9.SublimationToseparateamixtureofsolidsinwhichonlyonecansublime10.ChromatographyToseparateacomplexmixtureofsubstances(large/smallscale)Themixtureboilsbelow100CTechniqueAim6.FractionaldistIfthesubstanceisasolid,

itspuritycanbecheckedby determiningitsmeltingpointIfitisaliquid,

itspuritycanbecheckedby determiningitsboilingpointTestsforPurityIfthesubstanceisasolid,Te34.2IsolationandPurificationofOrganicCompounds(SBp.78)IsolationandPurificationofOrganicCompoundsTheselectionofapropertechnique

dependsontheparticulardifferences inphysicalpropertiesofthe substancespresentinthemixture34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.78)FiltrationToseparateaninsolublesolidfromaliquidparticularlywhenthesolidissuspendedthroughouttheliquidThesolid/liquidmixtureiscalledasuspension34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.78)FiltrationThelaboratoryset-upoffiltration34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.78)FiltrationTherearemanysmallholesinthefilterpaper

allowverysmallparticlesofsolvent anddissolvedsolutestopassthrough asfiltrateLargerinsolubleparticlesareretainedonthefilterpaperasresidue34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)CentrifugationWhenthereisonlyasmallamountofsuspension,orwhenmuchfasterseparationisrequired

Centrifugationisoftenused insteadoffiltration34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)CentrifugationTheliquidcontainingundissolvedsolidsisputinacentrifugetubeThetubesarethenputintothetubeholdersinacentrifugeAcentrifuge34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)CentrifugationTheholdersandtubesarespunaroundataveryhighrateandarethrownoutwardsThedensersolidiscollectedasalumpatthebottomofthetubewiththeclearliquidabove34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)CrystallizationCrystalsaresolidsthathave

adefiniteregularshape

smoothflatfacesandstraightedgesCrystallizationistheprocessofformingcrystals34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)1.CrystallizationbyCoolingaHotConcentratedSolutionToobtaincrystalsfromanunsaturatedaqueoussolution

thesolutionisgentlyheatedtomakeit moreconcentratedAfter,thesolutionisallowedtocoolatroomconditions34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)1.CrystallizationbyCoolingaHotConcentratedSolutionThesolubilitiesofmostsolidsincreasewithtemperatureWhenahotconcentratedsolutioniscooled

thesolutioncannotholdallofthe dissolvedsolutesThe“excess”soluteseparatesoutascrystals34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.79)1.CrystallizationbyCoolingaHotConcentratedSolutionCrystallizationbycoolingahotconcentratedsolution34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)2.CrystallizationbyEvaporatingaColdSolutionatRoomTemperatureAsthesolventinasolutionevaporates,

theremainingsolutionbecomes moreandmoreconcentrated

eventuallythesolutionbecomes saturated

furtherevaporationcauses crystallizationtooccur34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)2.CrystallizationbyEvaporatingaColdSolutionatRoomTemperatureIfasolutionisallowedtostandatroomtemperature,

evaporationwillbeslowItmaytakedaysorevenweeksforcrystalstoform34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)2.CrystallizationbyEvaporatingaColdSolutionatRoomTemperatureCrystallizationbyslowevaporationofasolution(preferablysaturated)atroomtemperature34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)SolventExtractionInvolvesextractingacomponentfromamixturewithasuitablesolventWateristhesolventusedtoextractsaltsfromamixturecontainingsaltsandsandNon-aqueoussolvents(e.g.1,1,1-trichloroethaneanddiethylether)canbeusedtoextractorganicproducts34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)SolventExtractionOfteninvolvestheuseofaseparatingfunnelWhenanaqueoussolutioncontainingtheorganicproductisshakenwithdiethyletherinaseparatingfunnel,

theorganicproductdissolvesinto theetherlayer34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)SolventExtractionTheorganicproductinanaqueoussolutioncanbeextractedbysolventextractionusingdiethylether34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)SolventExtractionTheetherlayercanberunofffromtheseparatingfunnelandsavedAnotherfreshportionofetherisshakenwiththeaqueoussolutiontoextractanyorganicproductsremainingRepeatedextractionwillextractmostoftheorganicproductintotheseveralportionsofether34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.80)SolventExtractionConductingtheextractionwithseveralsmallportionsofetherismoreefficientthanextractinginasinglebatchwiththewholevolumeofetherTheseseveraletherportionsarecombinedanddried

theetherisdistilledoff

leavingbehindtheorganicproduct34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.81)DistillationAmethodusedtoseparateasolvent

fromasolutioncontainingnon-volatilesolutesWhenasolutionisboiled,

onlythesolvent

vaporizes

thehotvapourformedcondensesto liquidagainonacoldsurfaceTheliquidcollectedisthedistillate34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.81)DistillationThelaboratoryset-upofdistillation34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.81)DistillationBeforethesolutionisheated,

severalpiecesofanti-bumping granulesareaddedintotheflask

preventvigorousmovementofthe liquidcalledbumpingtooccurduring heating

makeboilingsmooth34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.81)DistillationIfbumpingoccursduringdistillation,

somesolution(notyetvaporized) mayspurtoutintothecollecting vessel34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.81)FractionalDistillationAmethodusedtoseparateamixtureoftwoormoremiscibleliquids34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.82)FractionalDistillationThelaboratoryset-upoffractionaldistillation34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.82)FractionalDistillationAfractionatingcolumnisattachedverticallybetweentheflaskandthecondenser

acolumnpackedwithglassbeads

providealargesurfaceareaforthe repeatedcondensationandvaporization ofthemixturetooccur34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.82)FractionalDistillationThetemperatureoftheescapingvapourismeasuredusingathermometerWhenthetemperaturereadingbecomessteady,

thevapourwiththelowestboiling pointfirstlycomesoutfromthetopof thecolumn34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.82)FractionalDistillationWhenallofthatliquidhasdistilledoff,

thetemperaturereadingrisesand becomessteadylateron

anotherliquidwithahigherboiling pointdistilsoutFractionswithdifferentboilingpointscanbecollectedseparately34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.82)SublimationSublimationisthedirectchangeof

asolidtovapouronheating,or

avapourtosolidoncooling

withoutgoingthroughtheliquid state34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.82)SublimationAmixtureoftwocompoundsisheatedinanevaporatingdishOnecompoundchangesfromsolidtovapourdirectly

Thevapourchangesbacktosolidona coldsurfaceTheothercompoundisnotaffectedbyheatingandremainsintheevaporatingdish34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)SublimationAmixtureoftwocompoundscanbeseparatedbysublimation34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)ChromatographyAneffectivemethodofseparatingacomplexmixtureofsubstancesPaperchromatographyisacommontypeofchromatography34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)ChromatographyThelaboratoryset-upofpaperchromatography34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)ChromatographyAsolutionofthemixtureisdroppedatoneendofthefilterpaper34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)ChromatographyThethinfilmofwateradheredontothesurfaceofthefilterpaperformsthestationaryphaseThesolventiscalledthemobilephaseoreluent34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)ChromatographyWhenthesolventmovesacrossthesamplespotofthemixture,

partitionofthecomponentsbetweenthe stationaryphaseandthemobilephaseoccurs34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.83)ChromatographyAsthevariouscomponentsarebeingadsorbedorpartitioned

atdifferentrates,

theymoveupwardsatdifferentratesTheratioofthedistancetravelledbythesubstancetothedistancetravelledbythesolvent

knownastheRfvalue

acharacteristicofthesubstance34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.84)TechniqueAim(a)FiltrationToseparateaninsolublesolidfromaliquid(slow)(b)CentrifugationToseparateaninsolublesolidfromaliquid(fast)(c)CrystallizationToseparateadissolvedsolutefromitssolution(d)SolventextractionToseparateacomponentfromamixturewithasuitablesolvent(e)DistillationToseparatealiquidfromasolutioncontainingnon-volatilesolutesAsummaryofdifferenttechniquesof

isolationandpurification34.2IsolationandPurificati34.2IsolationandPurificationofOrganicCompounds(SBp.84)TechniqueAim(f)FractionaldistillationToseparatemiscibleliquidswithwidelydifferentboilingpoints(g)SublimationToseparateamixtureofsolidsinwhichonlyonecansublime(h)ChromatographyToseparateacomplexmixtureofsubstancesAsummaryofdifferenttechniquesof

isolationandpurificationCheckPoint34-234.2IsolationandPurificati34.4QualitativeAnalysisofElementsinanOrganicCompound34.4QualitativeAnalysisofEl34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)Qualitativeanalysisofanorganiccompoundis

todeterminewhatelementsare presentinthecompoundQualitativeAnalysisofanOrganicCompound34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)CarbonandHydrogenTestsforcarbonandhydrogeninanorganiccompoundareusuallyunnecessary

anorganiccompoundmust containcarbonandhydrogen34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)CarbonandHydrogenCarbonandhydrogencanbedetectedbyheatingasmallamountofthesubstancewithcopper(II)oxideCarbonandhydrogenwouldbeoxidized

tocarbondioxideandwaterrespectivelyCarbondioxideturnslimewatermilkyWaterturnsanhydrouscobalt(II)chloridepaperpink34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)Halogens,NitrogenandSulphurHalogens,nitrogenandsulphurinorganiccompoundscanbedetected

byperformingthesodiumfusiontest34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)Halogens,NitrogenandSulphurThecompoundundertestis

fusedwithasmallpieceofsodium metalinasmallcombustiontube

heatedstronglyTheproductsofthetestareextractedwithwaterandthenanalyzed34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)Halogens,NitrogenandSulphurDuringsodiumfusion,

halogensintheorganiccompoundis convertedtosodiumhalides

nitrogenintheorganiccompoundis convertedtosodiumcyanide

sulphurintheorganiccompoundis convertedtosodiumsulphide34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)ElementMaterialusedObservationHalogens,asAcidifiedsilvernitratesolutionchlorideion(Cl-)Awhiteprecipitateisformed.ItissolubleinexcessNH3(aq).bromideion(Br-)Apaleyellowprecipitateisformed.ItissparinglysolubleinexcessNH3(aq).iodideion(I-)Acreamyyellowprecipitateisformed.ItisinsolubleinexcessNH3(aq).Resultsforhalogens,nitrogenandsulphurinthesodiumfusiontest34.4QualitativeAnalysisof34.4QualitativeAnalysisofElementsinanOrganicCompound(SBp.86)Resultsforhalogens,nitrogenandsulphurinthesodiumfusiontestElementMaterialusedObservationNitrogen,ascyanideion(CN-)Amixtureofiron(II)sulphateandiron(III)sulphatesolutionsAblue-greencolourisobserved.Sulphur,as

sulphideion(S2-)Sodiumpentacyanonitrosylferrate(II)solutionAblackprecipitateisformedCheckPoint34-434.4QualitativeAnalysisof34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData34.5DeterminationofEmpirical34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)Afterdeterminingtheconstituentelementsofaparticularorganiccompound

performquantitativeanalysistofindthe percentagecompositionbymassofthe compound

themassesofdifferentelementsinan organiccompoundaredeterminedQuantitativeAnalysisofanOrganicCompound34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)1.CarbonandHydrogenTheorganiccompoundisburntinexcessoxygenThecarbondioxideandwatervapourformedarerespectivelyabsorbedby

potassiumhydroxidesolutionand anhydrouscalciumchloride34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)1.CarbonandHydrogenTheincreasesinmassinpotassiumhydroxidesolutionandcalciumchloriderepresent

themassesofcarbondioxide

and watervapourformedrespectively34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)2.NitrogenTheorganiccompoundisheatedwithexcesscopper(II)oxideThenitrogenmonoxideandnitrogendioxideformedarepassedoverhotcopper

thevolumeofnitrogenformedis measured34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)3.HalogensTheorganiccompoundisheatedwithfumingnitric(V)acidandexcesssilvernitratesolutionThemixtureisallowedtocool

thenwaterisadded

thedrysilverhalide

formedisweighed34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)4.SulphurTheorganiccompoundisheatedwithfumingnitric(V)acidAftercooling,

bariumnitratesolutionisadded

thedrybariumsulphateformedis weighed34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)QuantitativeAnalysisofanOrganicCompoundAfterdeterminingthepercentagecompositionbymassofacompound,

theempiricalformulaofthecompound canbecalculated34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)QuantitativeAnalysisofanOrganicCompoundTheempiricalformulaofacompoundistheformulawhichshowsthesimplestwholenumberratiooftheatomspresentinthecompound34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.87)QuantitativeAnalysisofanOrganicCompoundWhentherelativemolecularmassandtheempiricalformulaofthecompoundareknown,

themolecularformulaofthe compoundcanbecalculated34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.88)QuantitativeAnalysisofanOrganicCompoundThemolecularformulaofacompoundistheformulawhichshowstheactualnumberofeachkindofatomspresentinamoleculeofthecompound34.5DeterminationofEmpiric34.5DeterminationofEmpiricalFormulaandMolecularFormulafromAnalyticalData(SBp.88)Example34-5AExample34-5BCheckPoint34-534.5DeterminationofEmpiric34.6StructuralInformationfromPhysicalProperties34.6StructuralInformationfro34.6StructuralInformationfromPhysicalProperties(SBp.89)Thephysicalpropertiesofacompoundincludeitscolour,odour,density,solubility,meltingpointandboilingpointThephysicalpropertiesofacompounddependonitsmolecularstructureStructuralInformationfromPhysicalProperties34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.89)StructuralInformationfromPhysicalPropertiesFromthephysicalpropertiesofacompound,

obtainpreliminaryinformationabout thestructureofthecompound34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.89)StructuralInformationfromPhysicalPropertiese.g.

Hydrocarbonshavelowdensities, oftenabout0.8gcm–3

Compoundswithfunctionalgroups havehigherdensities34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.89)StructuralInformationfromPhysicalPropertiesThedensitiesofmostorganiccompoundsare<1.2gcm–3Compoundshavingdensities>1.2gcm–3mustcontainmultiplehalogenatoms34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.90)OrganiccompoundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsHydrocarbons(saturatedandunsaturated)Allhavedensities<0.8gcm–3• Generallylowbutincreaseswithnumberofcarbonatomsinthemolecule•Branched-chainhydrocarbonshavelowerboilingpointsbuthighermeltingpointsthanthecorrespondingstraight-chainisomersInsolubleSolublePhysicalpropertiesofsomecommonorganiccompounds34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.90)OrganiccompoundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsAromatichydrocarbonsBetween0.8and1.0

gcm–3GenerallylowInsolubleSolublePhysicalpropertiesofsomecommonorganiccompounds34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.90)OrganiccompoundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsHalo-alkanes• 0.9-1.1gcm–3forchloro-alkanes•>1.0gcm–3forbromo-alkanesandiodo-alkanes• Higherthanalkanesofsimilarrelativemolecularmasses

(

haloalkanemoleculesarepolar)• Allhaloalkanesareliquidsexcepthalomethanes• Boththem.p.andb.p.

increaseintheorder:RCH2F<RCH2Cl<RCH2Br<RCH2IInsolubleSolublePhysicalpropertiesofsomecommonorganiccompounds34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.90)Organiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsAlcohols• Simplealcoholsareliquidsandalcoholswith>12carbonsarewaxysolids• Muchhigherthanhydrocarbonsofsimilarrelativemolecularmasses(

formationofhydrogenbondsbetweenalcoholmolecules)•Lowermembers:Completelymisciblewithwater(

formationofhydrogenbondsbetweenalcoholmoleculesandwatermolecules)SolublePhysicalpropertiesofsomecommonorganiccompounds34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.90)PhysicalpropertiesofsomecommonorganiccompoundsOrganiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsAlcohols• Allsimplealcoholshavedensities

<1.0gcm–3• Straight-chainalcoholshavehigherb.p.thanthecorrespondingbranched-chainalcohols•SolubilitydecreasesgraduallyasthehydrocarbonchainlengthensSoluble34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.91)PhysicalpropertiesofsomecommonorganiccompoundsOrganiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsCarbonylcomp-ounds(alde-hydesandketones)• <1.0gcm–3foraliphaticcarbonylcompoundsHigherthanalkanesbutlowerthanalcoholsofsimilarrelativemolecularmasses(Moleculesofaldehydesorketonesareheldtogetherbystrongdipole-dipoleinteractionsbutnothydrogenbonds)•Lowermembers:

Solubleinwater(

theformationofhydrogenbondsbetweenmoleculesofaldehydesorketonesandwatermolecules)Soluble34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.91)PhysicalpropertiesofsomecommonorganiccompoundsOrganiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsCarbonylcomp-ounds(alde-hydesandketones)• >1.0gcm–3foraromaticcarbonylcompounds•SolubilitydecreasesgraduallyasthehydrocarbonchainlengthensSoluble34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.91)PhysicalpropertiesofsomecommonorganiccompoundsOrganiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsCarbo-xylicacids• Lowermembershavedensitiessimilartowater•Methanoicacidhasadensityof1.22gcm–3Higherthanalcoholsofsimilarrelativemolecularmasses(

theformationofmoreextensiveintermolecularhydrogenbonds)•Firstfourmembersaremisciblewithwaterinallproportions•SolubilitydecreasesgraduallyasthehydrocarbonchainlengthensSoluble34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.91)PhysicalpropertiesofsomecommonorganiccompoundsOrganiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsEstersLowermembershavedensitieslessthanwaterSlightlyhigherthanhydrocarbonsbutlowerthancarbonylcompoundsandalcoholsofsimilarrelativemolecularmassesInsolubleSoluble34.6StructuralInformationf34.6StructuralInformationfromPhysicalProperties(SBp.91)PhysicalpropertiesofsomecommonorganiccompoundsOrganiccomp-oundDensityat20oCMeltingpointandboilingpointSolubilityInwaterorhighlypolarsolventsInnon-polarorganicsolventsAminesMostamineshavedensitieslessthanwater• Higherthanalkanesbutlowerthanalcoholsofsimilarrelativemolecularmasses• Generallysoluble•Solubilitydecreasesintheorder: 1oamines