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    Writing Resonance Structures PDF

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    Chamila Rajapaksha
    This document provides guidelines for writing resonance structures. Resonance structures show how electron delocalization influences chemistry. Rules include: (1) structures must differ only in electron positions, not atom positions; (2) a double-headed arrow connects structures to show electron motion between them; and (3) only unshared electrons and pi-bond electrons can move. Curly arrows indicate electron motion between valid Lewis structures while maintaining the overall charge. Following examples demonstrate how to systematically generate resonance contributors.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd

    Writing Resonance Structures PDF

    Uploaded by

    Chamila Rajapaksha
    586 views5 pages
    This document provides guidelines for writing resonance structures. Resonance structures show how electron delocalization influences chemistry. Rules include: (1) structures must differ only in electron positions, not atom positions; (2) a double-headed arrow connects structures to show electron motion between them; and (3) only unshared electrons and pi-bond electrons can move. Curly arrows indicate electron motion between valid Lewis structures while maintaining the overall charge. Following examples demonstrate how to systematically generate resonance contributors.

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    This document provides guidelines for writing resonance structures. Resonance structures show how electron delocalization influences chemistry. Rules include: (1) structures must differ only in electron positions, not atom positions; (2) a double-headed arrow connects structures to show electron motion between them; and (3) only unshared electrons and pi-bond electrons can move. Curly arrows indicate electron motion between valid Lewis structures while maintaining the overall charge. Following examples demonstrate how to systematically generate resonance contributors.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    586 views5 pages

    Writing Resonance Structures PDF

    Uploaded by

    Chamila Rajapaksha
    This document provides guidelines for writing resonance structures. Resonance structures show how electron delocalization influences chemistry. Rules include: (1) structures must differ only in electron positions, not atom positions; (2) a double-headed arrow connects structures to show electron motion between them; and (3) only unshared electrons and pi-bond electrons can move. Curly arrows indicate electron motion between valid Lewis structures while maintaining the overall charge. Following examples demonstrate how to systematically generate resonance contributors.

    Copyright:

    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    of 5

    11/4/2016

    WritingResonanceStructures

    WritingResonanceStructures
    We'regoingtomakealotofuseofresonancetoshowhow
    delocalizationofelectronsinfluenceschemistry.Thispagepresents
    afewrulestokeepinmindwhendrawingthestructures.
    Moleculesthatrequiredescriptionwithresonancearethosefor
    whichwecanwritetwoormoreLewisstructuresthatdifferonly
    inthepositionofelectrons
    Ifthestructuresdifferinthepositionofatoms,theyare
    isomers,notresonancestructures

    Becausetheydifferonlyinthepositionsofelectrons,wecan
    showhowresonancestructuresarerelatedbyshowingthe
    electronmotionsthatwouldchangeoneresonancestructure
    intotheother.

    Itiscustomarytouseadoubleheadedarrowtoconnect
    resonancestructuresdonotmistakethisforthedoublearrow
    indicatingequilibrium.

    http://chemistry.umeche.maine.edu/CHY251/Reson.html

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    11/4/2016

    WritingResonanceStructures

    Onlyunsharedelectronsandelectronsthatarepartofmultiple
    bonds(bonds)canbemovedindrawingresonance
    structuresthatis,resonancecanoccuronlyinthosepartsof
    moleculesthatarecomposedofsporsp2atomsporbitalsare
    anabsoluterequirementforresonance!
    Tostart,weneedavalidLewisstructureforthespeciesweare
    examining.
    Withoutchangingthenumberofunpairedelectrons(andswitching
    betweenionsandradicalsalwaysdoesthis,soweavoiddoingit),
    usecurlyarrowstomoveoneortwopairsofelectronstocreate
    anothervalidLewisstructure.
    Herearesomethingstokeepinmindwhendecidingwhichelectron
    pairstomove.
    Movefewerelectronpairsratherthanmore
    Ingeneral,moveelectronsfromregionsofhighelectrondensity
    (unsharedpairs,C=Cdoublebonds)towardregionsoflow
    electrondensity(carbocationcenters,C=Odoublebonds,nitro
    groups)
    Hereisanexample,inwhichwewritetheresonancestructuresfor
    thespeciesinthemiddle:

    http://chemistry.umeche.maine.edu/CHY251/Reson.html

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    WritingResonanceStructures

    Followtheredarrowfirst.Seethatitconvertsanunsharedpair
    intoabondingpair.
    Workoutthenewformalchargessincewemovedelectrons
    awayfromthenitrogen,itshouldbecomepositive,andthe
    carbonreceivingthemshouldbecomemorenegative(going
    from+1to0isbecomingmorenegative).
    Nowfollowthebluearrows.Theleftarrowconvertsan
    unsharedpairintoabondingpairtheotherbluearrowdoesthe
    oppositeconversion.
    Wemovedelectronsawayfromanegativecarbonit
    becomesmorepositive.Apositivecarbonreceived
    electronsandbecameneutral.
    Somegeneralrules:
    Theheadofacurlyarrowalwaysmakesabondoranunshared
    pair.
    Thetaileitherbreaksabondormakesanunsharedpairintoa
    sharedpair.
    Ifseveralpossibilitiesformovingelectronsexistwithinagiven
    structure,tryeachofthem,butseparately.
    Bothoftheresultingstructuresintheexamplearevalid
    resonancecontributors.However,someresonancestructures
    aremoreequalthanothers(GeorgeOrwell):

    http://chemistry.umeche.maine.edu/CHY251/Reson.html

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    11/4/2016

    WritingResonanceStructures

    Structuresinwhicheveryatomhasanoctet,liketheoneonthe
    right,arebetterthanthoseinwhichanatomismissing
    electrons,liketheoneontheleft.
    Structuresthatresultfromcreatingchargesonformerlyneutral
    structures,onthecontrary,areunfavorableavoidthemif
    possible.
    Finally,althoughformalchargesonindividualatomsmaychange
    fromstructuretostructure,thenetchargeonthestructureMUST
    remainthesame.Otherwise,youarecreatingordestroying
    electrons,andMotherNaturedoesn'tlikethat.
    Noticeherethatthestartingstructurehasformalchargesthatadd
    uptozerosodobothresonancestructuresthatwedrew.
    Here'sanotherexample:

    Here,theoriginalstructureisontheleft,andwegeneratedthethird
    structurefromthesecond.Onecannotknowaheadoftimewhether
    allstructurescanbegeneratedfromtheoriginalorfromeachother,
    orboth.Onesimplykeepstrying,untilnonewstructuresseemto
    appear.
    Specieswithunpairedelectronscanhaveresonancestructures
    also.
    Inthesecases,moveelectronsoneatatimeratherthaninpairs
    Usecurlyarrowswithonlyonebarb(curlyfishhooks?)tomove
    singleelectrons
    http://chemistry.umeche.maine.edu/CHY251/Reson.html

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    WritingResonanceStructures

    Herearesomeexercisestousetopractice:

    Rememberthatnoneofthestructureswedrawhasanyobjective
    realitywewouldhavetodrawthemolecularorbitalsderivedfrom
    systemsofoverlappingporbitalstoachievethat.

    [MythankstomyformercolleagueatKentStateUniversity,ProfessorEmeritusJohnGordon,forthe
    outlineoftheseideas.]
    Thispagelastmodified10:32AMonTuesdayJuly3rd,2012.
    Webmaster,DepartmentofChemistry,UniversityofMaine,Orono,ME04469

    http://chemistry.umeche.maine.edu/CHY251/Reson.html

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