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

Becausetheydifferonlyinthepositionsofelectrons,wecan
showhowresonancestructuresarerelatedbyshowingthe
electronmotionsthatwouldchangeoneresonancestructure
intotheother.

Itiscustomarytouseadoubleheadedarrowtoconnect
resonancestructuresdonotmistakethisforthedoublearrow
indicatingequilibrium.

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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:

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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):

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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
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Herearesomeexercisestousetopractice:

Rememberthatnoneofthestructureswedrawhasanyobjective
realitywewouldhavetodrawthemolecularorbitalsderivedfrom
systemsofoverlappingporbitalstoachievethat.

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

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