Chem31.

1zzzGroup2
DatePerformed:Feb.5,2015
GroupMembers:Cepeda,RalphDuhalngon,JeiaDateSubmitted:Feb.13,2015
Fabricante,JeremiasFajardo,Angel

Experiment2
SOLUBILITYBEHAVIOROFORGANICCOMPOUNDS
Cepeda,RalphDuhalngon,JeiaFabricante,JeremiasFajardo,Angel
CollegeofScience
UniversityofthePhilippinesBaguio

Abstract

The experimentaimed torelate the organic compounds structures to theirsolubilityandtoclassify

the organic compounds as waterether soluble (S1),water soluble(S2),strong acid(A1), weak acid (A2),
base (B), neutral (N), miscellaneous neutral (M), and inert (I). The solubility of each compound wasfirst
tested in 1mLofwater, andthen compounds thatresultedaspositiveor solublewerefurther testedinether
and those which are insoluble were tested in 5% NaOH. Compounds which are soluble in ether were
classified as S1 and those that did not, as S2. Then, soluble compounds in NaOH were tested in 5%
NaHCO3and insolublecompoundswith5%HCL.Insoluble testcompoundswithoutNorSin theirchemical
formula were testedinconcentratedH2SO4.Compounds thatmanifestedreactions suchaschangein color,
productionof heat,formationofprecipitate,orevolutionof gasin thesaid reactionwererecordedassoluble.
Benzamide and aniline were insoluble to water, NaOH and HCl, but were soluble in H2SO4 and were
labeledasneutral compounds. Benzaldehyde, toluene, and hexaneareS2 orcompoundssolubleinwater
Benzyl alcohol,ethanol,phenol,sucrose,and acetoneontheotherhandwereS1whichwereonlysolublein
water and not in ether. Benzoic acid was insoluble in water but soluble in NaOH. The experiment was
successfulbecausethesolubilityof allthetestcompoundsinthegivensolventsweredetermined,observed
andfurther classified. Basedonobservedreactions, acetone,ethylalcoholandsucrose whichweresoluble
in waterand ether were classifiedas S1 orwaterethersolublecompounds.Hexaneandphenolwhich were
insoluble in water but soluble in NaOH and NaHCO3 were classified as A1 or strong acids. Benzamide
which was insolubleinwater andNaOHbutinsolubleinNaHCO3wasclassifiedasA2orweakacid.Benzyl
alcohol,toluene, andbenzaldehydewhichwere insoluble in water,NaOH andHClbut reactedwithH2SO4
were neutral aniline was a miscellaneous neutral compound because it did not react to any of the test
solventswhilebenzoicacidisinertbecauseitwasnotdissolvedinthesolvents.

Introduction
Oneimportantpropertythatorganiccompoundsexhibitisthattheirstructureisrelatedtotheir
solubility.Solubilityistheamountofasubstancethatwilldissolveinagivenamountofanothersubstance
andistypicallyexpressedasthenumberofpartsbyweightdissolvedby100partsofsolventataspecified
temperatureandpressureoraspercentbyweightorbyvolume.Thegeneralruleusedindetermining
whetherasoluteissolubleorinsolubleinagivensolventislikedissolveslikewherenonpolarsolutes
dissolveinnonpolarsolventspolarsolutesdissolveinpolarsolventsorchemicalreactionsmayoccur
betweenthesolventandthesolutecausingdissolution.
Compoundsthatarebranchchainedaremoresolublethanthecorrespondingstraightchained
compound.Branchinglowersintermolecularforcesanddecreasesintermolecularattraction.Thepositionof
thefunctionalgroupinthecarbonchainalsoaffectssolubility.
The solubility of organiccompoundsin organicsolvents shouldbedeterminedinorderto planfora
variety of laboratoryoperationswhichinclude choosing solventsfororganicreactions,dissolvingsubstrates

for spectral analyses, cleaning glassware, extraction, thin layer and other chromatography and
crystallization.
Knowledge of the solubility of organic compounds is essential tool to a budding chemist. In
designingindustrialprocessessuch as crystallization andliquidextraction process,anunderstanding ofthe
solubility behavior of different chemicals is essential in selecting an appropriate solvent (Jiangang et al,
2014). In this experiment, the different solubility behaviors of organic compounds were examined. The
obtained results have pave way for the classification of compounds. Each test has allowed students to
classifytheorganiccompoundaseithersolubleorinsolubleineachofthetestsolvents.
Test organic compounds that are hydrocarbons such as toluene were insoluble in water. This is
because oftheir nonpolarnature.Inaddition,ifthereisapolarfunctionalgroupinacertaincompoundsuch
asinthecaseofbenzaldehyde,itisslightlysolubleinwater.
Ingeneral,theresults cemented the conceptoflike dissolveslike.Asobservedintheexperiment,
polar substances such acetone is readily miscible with water. In contrast, non polar molecules such as
hexane are insoluble with water. Consequently, the experiment shed light on the intermolecular forces
governing attraction between and among molecules. This is best exhibited by sucrose, a partially polar
substance yet it was dissolved in water due tothestrongersolventsolutebonding formation compared to
thesolventsolventorsolutesolutemolecularinteractions.
Theobjectivesoftheexperimentweretorelatetheorganiccompoundsstructurestotheirsolubility
andtoclassifytheorganiccompoundsaswatersoluble(S1),ethersoluble(S2),strongacid(A1),weakacid
(A2),base(B),neutral(N),miscellaneousneutral(M),andinert(I).

ResultsandDiscussion
Hexane
Hexane is a nonpolar compound thats why it is insoluble in water which is a polar solvent. A
nonpolarcompoundis hard todissolvebecauseofthepresenceofHbonding.Thedissolutionof hexaneis
following thelike dissolveslikeprinciplebecauseNaOHisastrongbasethusdissolvinghexanewhichisa
strongacid.HexanealsodissolvedinNaHCO
becauseitisastrongacidformingwatersolublesalts.
3
Benzamide
All nonpolar compounds are insolubleinwater, this isthereasonwhybenzamide didnotdissolve
in waterthus dissolving it in NaOH.NaOHisastrongbasethationizesweakacidswhereasbenzamide isa
weak acid.NaHCO
3is added to benzamide because it issoluble in NaOH.Less acidic compounds do not
dissolveinNaHCO
thereforethereisnoformationofwatersolublesalts.
3
Acetone
Acetone is the most common ketone thus its a polar compound. Following the principle like
dissolves like, water (a polar compound) dissolves acetone. Compound that dissolves in water also
dissolvesinNaOH,NaCHO
,HCl,andH
SO
becausealltheseareprimarilywater.
3
2
4
Ethylalcohol
Six drops of ethylalcohol was mixedwithonemillilitre ofwater. Theresultingsolution wasaclear
liquid solution.The physical descriptionimpliesthatethyl alcoholismiscibleinwater.Theresultalsotellsus
thatethylalcoholmusthaveapolarbondsincewaterisapolarcompound.

Ethanol is a compound with nonpolar and polar bonds. Ethanols formula looks like this:
CH
CH
OH.
The bonds between the carbons are nonpolar, while the bond of the OH group of the
3 2
compound is polar . The strength of the attraction of the OHgroup makes itcompletelymisciblein water
(SolubilityofThings,n.d.).
After being determined as water soluble, ethyl alcohols solubility was tested using ether as a
solvent. Ethyl alcohol was also dissolved in the mixture. Theresultof the experimentsuggeststhat ethyl
alcoholisalsoethersoluble.
Ethers are slightly polar,whichexplains thedissolvingof theethylalcohol.Ethers,Diethyletherfor
example,are also nonpolar compounds usedto determine ifawatersolublecompoundis extremelypolar.
Asubstancecannotbe dissolvedinether ifit is. Butsince ethylalcoholwas dissolved,it isnotextremely
polar.
Benzylalcohol
When benzyl alcoholwasmixed withwater, the resulting mixturehad twolayers. Thismeansthat
benzyl alcoholwasnotsoluble in waterdespitebeinganalcohol.Beinganalcohol, benzylalcoholisapolar
compound. Alcohols with one to three carbons are completely miscible in water, but the solubility of the
alcohol decreases asthenumber ofcarbonincreases .Benzylalcohol contains sevencarbonatomswhich
makesitpartiallysolubleinwater.
Two common functional groups dissolve in sodium hydroxide, which are carboxylic acids and
phenols (University of Puget Sound, n.d.). Benzyl alcohol is neither of the two explaining why it did not
dissolveinNaOH.
The5%HClsolutionwasunabletodissolvethebenzylalcoholbecauseHCldissolvesbasic
compoundsunlikebenzylalcoholwhichhasaslightacidicproperty.
Concentratedsulfuricacidisquicklyabletodissolvebenzylalcohol.Theresultingsolutionhad
changeincolor,releaseofheatandformationofprecipitate.Sulfuricacidprotonatescompoundscontaining
oxygen.Sulfuricacidwasusedtotestwhetheracompoundwithoutnitrogenorsulphurisaneutral
compoundoranextremelyweakbase.
Aniline
Similarlytothebenzylalcohol,amideslikeanilinearesolubletowater,but,sinceanilinehassix
carbons,itssolubilityinwaterdecreases.Alsolikebenzylalcohol,anilineisnotaphenoloracarboxylic
acid.Hence,therewasnoreactionwithsodiumhydroxide(UniversityofPugetSound).Sinceaniline
containsnitrogen,itwasnottestedwithsulfuricacidandwasclassifiedasa
miscellaneousneutralcompound.
Sucroseissolubleinwaterbecausethebondformationbetweenthesolventsoluteinteractionsis
strongenoughtodisrupttheweakbondsbetweenindividualmoleculesofsucroseandthehydrogenbondin
water.Thisisalsobecausewaterisapolarsolventandsucroseispartiallypolarmolecule.Assuch,therule
ofthethumbthatlikedissolveslikeclearlyapplieshere.Likewise,sucrosehasbeenslightlysolublein
etherbecauseoftheslightpolarityofthelatter.Polarityoftheetherisduetotheelectronegativitydifference
betweenitsoxygenandcarbonatoms.Hence,sucrosecouldbeclassifiedaswaterethersoluble
compound.
Ontheotherhand,tolueneisimmiscibletowaterduetothefactthattheyarenonpolarandpolar,
respectively.Thesameprincipleapplieswhentolueneissubjectedto5%NaOH.Asapolarmolecule,
sodiumhydroxidedoesnotreactwithnonpolarmolecules.However,whensubjectedunderconcentrated
sulfuricacid,thetoluenereactsbychangingitscolor.Themechanismbehindthisisthatsulfuricacid
interactswithtoluenethroughelectrophilicaromaticsubstitution.ElectrophilicAromaticSubstitution(EAS)is
asubstitutionreactionusuallyinvolvingthebenzeneringmorespecificallyitisareactioninwhichthe

hydrogenatomofanaromaticringisreplacedasaconsequenceofelectrophilicattackonthearomatic
ring.Asinthecaseoftoluene,itsbenzeneringwasattackedbytheelectronrichsulfuricacid.Thatswhy,
miscibilityoccurredbetweenthetwocompoundsandtolueneisclassifiedasneutralcompound.
Intermsofthesolubilityofbenzaldehyde,itissparinglysolubleinwater.Despitethenonpolarity
behaviorofitsbenzenering,anadditionofthealdehydefunctionalgroupmakesbenzaldehydeslightly
polar.Thus,thereisaminimalsolubilityinthesaidcompounds.Inthecaseofbenzaldehydessolubilitywith
ether,itisalmosthomogenous.Thisisbecausethelargehydrophobicaromaticringofbenzaldehydecould
readilyreactwithnonpolarsolventsuchasether.
Benzoicacidsolubility
Theprimaryreasonbenzoicacidisonlyslightly,barelyornotatallsolubleincoldorroom
temperaturewateristhat,eventhoughthecarboxylicacidgroupispolar,thebulkofthebenzoicacid
moleculeisnonpolar(waterispolar).Itisonlythecarboxylicgroupthatispolar.Also,carboxylicacidssuch
asbenzoicacidarerelativelyweakacids,andthusexistmostlyintheacidic(protonated)formwhenadded
topurewater.However,ionization,increaseinpH,orincreaseintemperatureincreasesthesolubilityofthe
benzoicacidmoleculeinwater.Theexplanationbehindthisisthatthehydrogenbonding,hydrophiliceffect
ofthecarboxylicacidgroupisnotpowerfulenoughtoovercomethelargerhydrophobiceffectofthe
6carbonbenzenegrouponbenzoicacid.

Phenol
PhenolsshowacidicnatureandhencearesolubleinalkalieslikeNaOH,Na
CO
etc.Theacidic
2
3
natureisduetoformationofresonancestabilizedphenoxideionformedbylosingaprotonfromOHgroup.
Phenolisalsosolubleinwatertosomeextent,althoughitdidnotdissolveduringtheexperiment.Itisdueto
itsabilitytoformhydrogenbondingwithwatermolecules.Howeverthelargepartofphenolmoleculeis
phenylgroupthatisnonpolarandhenceitssolubilityiflimitedinwater.Whenalkaliesareaddedtophenol,
+

theaboveequilibriumisshiftedmoretotherightsideastheH
ionsareremovedbytheOH
ionsthatare

furnishedbyalkalies.Thusmoreandmorephenolisconvertedtophenoxideionthatissolubleinwater.

NaHCO
isnotastrongalkaliandhenceitcannotprovideasmuchOH
ionsthatarerequiredtoshiftthe
3
abovementionedequilibrium.Henceonlysmallamountofphenoxideisformed.Hencephenolissparingly
solubleinNaHCO
.
3

SummaryandConclusion
Basedonthedatagatheredandobservationsmade,thestudentsclassifiedhexaneandphenol,
whichwereinsolubleinwater,butsolubleinNaOHandNaHCO3asstrongacids(A1).Ethylalcohol,
acetoneandsucrosewereclassifiedaswaterethersolublecompounds(S1).Then,benzamidewas
classifiedasaweakacid(A2)afteritwasfoundouttobeinsolubleinwaterandNaHCO3butsolublein
NaOH.Anilineandbenzoicacidwereclassifiedasamiscellaneousneutralcompoundandaninert
compoundrespectivelyafternotshowingsolubilityinanyofthesolvents.Benzylalcohol,tolueneand
benzaldehydewhichwereinsolubleinwater,NaOHandHClbutshowedsignsofchemicalreactionwith
H2So4wereclassifiedasneutralcompounds(N).

ANSWERSTOQUESTIONS
1.

Whatarethetypesofintermolecularforcespresentinsolutionsformeddueto
solventsoluteinteractions?
Basedontheresultsoftheexperiment,onlythreeorganictestcompounds
(sucrose,acetoneandethylalcohol)weresolubleinwater.Itimpliesthatthehydrogen
bondinginthewatermoleculesandthedipoledipoleinteractionsamongthepolarsolute
moleculeswerereplacedbyhydrogenbondingbetweenthesoluteandthesolvent.These
threewerealsodissolvedinethermakingthetestcompoundsnonpolarsinceetherisa
nonpolarcompound.EtherwasabletodissolveacetoneandethylalcoholbyLondon
DispersionForce.Dispersionforcesexistbetweenallkindsofmoleculesduetothe
movementofelectronswithinthemolecule,creatingamomentarydipole.Waterisapolar
moleculewithoxygencarryingapartialnegativechargeandhydrogenwithapartialpositive
charge,thusexhibitsdipoledipoleforces.Inaddition,theOHbondinthemoleculeallows
hydrogenbondingbetweenthemolecules.Therefore,foraqueoussolutionsofsucrose,
ethylalcoholandacetonewhichareallpolarmolecules,thepredominantintermolecular
forcesaredipoledipoleforces,hydrogenbondinganddispersionforces.Ontheotherhand,
diethyletherisessentiallyanonpolarsolventandcanonlydissolvenonpolar
substances.Dipoledipoleforcescannotexistbetweennonpolarmoleculesbecauseofthe
lackofadipoleinitsstructure,hencetheonlysignificantintermolecularforcesbetween
nonpolarmolecules,suchasthoseinethersolutionsofethylalcoholandacetone,are
dispersionforces.

2.

Tosumitup:
AcetoneH2OLondondispersion,dipoledipole,Hbonding
EthylalcoholH2OLondondispersion,dipoledipole,Hbonding
SucroseH2OLondondispersion,dipoledipole,Hbonding
AcetoneEtherLondondispersion
EthylalcoholEtherLondondispersion
Writethebalancedchemicalequationsofthesolventsolutecombinationsthatformed
solutionsduetochemicalreactions.

3.

Onthebasisofsolubilitybehavior,showhoweachofthefollowingpairsofcompoundsmay
bedistinguishedfromeachother.
a.CH NHCH andCH (CH ) CH NH
CH3NH2isasmall,polarmolecule,thatcanhydrogenbondwithH2O.
CH3(CH2)5CH2NH2isalsocapableofhydrogenbondingwithH2Othroughthe
aminogroupsbutislesserpolarbecauseofthepresenceofamuchlonger,
nonpolar,hydrocarbonchain.

b.Ethanalandhydroxyethanal
CH3CHOisasmall,polarmolecule,thatcanalsohydrogenbondwith
H2OthroughtheOontheC=Ogroup.HOCH2CHisalsosmall,polar,andcan
alsohydrogenbondwithH2OthroughOHgroupinadditiontohydrogenbonding
withH2OthroughtheOontheC=Ogroup.

c.Benzylamineandbenzylalcohol
Thecompoundsthatcontainthelarge,nonpolar,benzeneringsarenot
thatverysolubleinH2O.Aminesandalcoholsarebothcapableofforming
hydrogenbondswithH2O,butalcoholshavethestrongerhydrogenbonding.Also,
benzylamineissolubleinHClbutbenzylalcoholisinsoluble.

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