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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
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