CAPECHEMISTRYMAY/JUNE2012UNIT1PAPER2 QUESTION1CRAMSHEET

(a) Adativecovalentorcoordinatecovalentbondisoneinwhichoneoftheatomssuppliesboththesharedelectronstothecovalent bond.AdativecovalentbondiswrittenAB,wherethedirectionofthearrowshowsthedirectioninwhichtheelectronpairis donated.Anexampleofthisistheammoniumion(NH4+)whichisformedwhenammonia(NH3)bondswithaproton(H+),withthe bondingelectronscomingfromNH3.Theammoniumionhasthreecovalentbondsandonedativecovalentbond. Theinvolvementoftheelectronpairasadative covalentbondisoftenshownasanarrow.Note thatonceNH4+ hasformed,allfourbondsare equivalentandyoucannottellwhichwasformed byadativecovalentbond

NH3

NH4+

(b) Neutral but polar molecules experience dipole dipole forces as the result of Neutralbutpolarmoleculesexperiencedipoledipoleforcesastheresultof electricalinteractionsamongdipolesonneighboringmolecules.The strengthofagivendipoledipoleinteractiondependsonthesizesofthe dipolemomentsinvolved.Themorepolarthesubstance,thegreaterthe strengthofitsdipoledipoleinteractions.Butane,forinstance,isanonpolar moleculewitharelativemolecularmassof58andaboilingpointof0.5C, whilepropanone hasthesamemolecularmassyetboils57Chigher becauseitispolar.Thetablewhichfollows,listsallthedifferent intermolecularforces.Iondipoleforcesarenotrelevanttothisquestion. p q

Butane(C4H10)Propanone (C3H6O)

Alcoholsandhydrogenbonding Alcoholshave higherboilingpointsthanotherorganicmolecules ofsimilarmolecularmass,betweenwhich hydrogenbondingisnotpresent.Theboilingpoint ofpropan1ol(rmm of60),isexpectedtobe higherthanbothbutaneandpropanone.Indeed,it is97C.

(c) Factorsaffectingsolubility Thereisanoldsayinginsciencethatsays,likedissolveslike.Itmeansthatsubstancesthataresimilar shouldformasolution.Italsoimpliesthatsubstancesthatarenotsimilarshouldnotformasolution.Asageneralruleof thumb,like dissolveslikeworksprettywell.Thetermlikereferstotheoverallpolarityofthesolventmolecule(whetherpolarornonpolar)and theoverallpolarityofthesolute(whetherpolar,nonpolar,oranionicspeciesthatisaccommodatedbypolarsolvents). Polarspecies:Moleculeswithapermanentdipoleand/ortheabilitytoengageinhydrogen bonding.Waterisaperfectexampleofa polarspecies.Itisabent,polarmoleculewithasubstantialabilitytohydrogenbond.Alcoholsarealittlelesspolar,buttheyand polar species It is a bent polar molecule with a substantial ability to hydrogen bond Alcohols are a little less polar but they and sugarscanengageinstronghydrogenbonding.Water,becauseofitspolarity,isuniquelysuitedtoaccommodatepositiveand negativeionsinsolution,makingitanexcellentsolventformanyioniccompounds. Nonpolarspecies:Moleculesthatdonothaveapermanentdipoleanddonothavetheabilitytoengageinhydrogenbonding.Many covalent,organicliquidsfallintothiscategory:oils,solventsderivedfrompetroleum,carbontetrachloride(CCl4),andsoon.Polarand ioniccompoundsaremorelikelytodissolveinapolarsolvent,likeH2O,thaninanonpolarsolventlikeCCl4 oroil.Polarwater moleculesarenotsolubleinoilorcarbontetrachloride,bothofwhicharenonpolarliquids.However,nonpolarcompounds,likeoils, aresolubleinnonpolarsolventsbutarenotsolubleinpolarsolventslikewater.Thelikelihoodofformingasolutionusingsolvents andsolutesofdifferingpolarityissummarizedinthefollowingtable.Keepinmindthatpolar/ionicnonpolarcomparisonshave some gp y g p p / p p limitations.Notallioniccompoundsaresolubleinwater,butthosethataredonotdissolveinnonpolarsolvents. When propane dissolves inwater,it forms hydrogen bonds bonds withwater molecules. Propanone andwater Inliquidsofhighpolaritysuchaswater, therearestrongwater waterattractions. Theseareconsiderablystrongerthaneither iodineiodineattractionsoriodinewater attractions.Consequentlyiodinemolecules cannotpenetratethewaterstructureand thereislittletendencyforwatermolecules there is little tendency for water molecules tosolvateunchargediodinemolecules. Iodineisthereforealmostinsolubleinwater. Iodineandwater Innonpolarliquidssuchasbenzeneand tetrachloromethane,thereareweak intermolecularforces.Thebenzenebenzene attractionsaresimilarinstrengthtoiodine benzeneandiodineiodineattractions.Thus itiseasyforbenzenemoleculetopenetrate intotheiodinecrystalandsolvatetheiodine into the iodine crystal and solvate the iodine molecules.Consequentlyiodinedissolves easilyinbenzene. Iodineandnonpolarsolvent

CAPECHEMISTRYMAY/JUNE2012UNIT1PAPER2 QUESTION1MARKSCHEME
(a) Oneinwhichoneoftheatomssuppliesboththesharedelectrons tothecovalentbond[1mark] Diagramshowingformationofbond[1mark] C,A,B[1mark] A vander Waalsforces(permanentdipole permanentdipole)and LondonForces(temporarydipole d l f ( d l d l ) d d ( d l induceddipole)[1mark] B Hydrogenbondsand LondonForces(temporarydipole induceddipole)[1mark] C vander Waalsforces(permanentdipole permanentdipole)and LondonForces(temporarydipole induceddipole)[1mark] Permanentdipole permanentdipole Differenceinelectronegativity betweentwoatoms(CandOinpropanone)leavespermanent onCand onO Difference in electronegativity between two atoms (C and O in propanone) leaves permanent + on C and on O [1mark] Attractionbetweendipolesistheforceholdingmoleculestogether[1mark] Hydrogenbonds HydrogenwhenbondedtoF,OorNlosesalmostallofthebondingelectrondensitytotheotheratom[1mark] Verylarge+ onHisstronglyattractedtolonepaironF,OorNofanothermoleculeofthesamecompound[1mark] Londonforces Temporaryfluctuationsinelectrondensityresultinsmall,temporarydipolesonamolecule[1mark] Temporarydipolesinducedipolesofoppositesignonnearbymoleculesandattractionresults[1mark] (c) Potassium bromide Solubleinwater[1mark] Insolubleintoluene[1mark] l bl l [ k] Acetone Solubleinwater[1mark] SolidIodine Insolubleinwater[1mark] thisiswhatCAPEwouldwant,eventhoughitisnottrue. Insoluble in water [1 mark] this is what CAPE would want even though it is not true Solubleintoluene[1mark]

(b)(i) (b)(ii) (b)( )

(b)(iii)