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Asimpletrick:The(R)(S)Toggle
byJames
inOrganicChemStudyTips,OrganicChemistry1,Stereochemistry

Thedifficultyofassigning(R)/(S)toastereocentercanbehighlydependentonthewaythemoleculeisdrawn.
Forexample,assigningthestereochemistryofAshouldbeacakewalkifyouaretheleastbitfamiliarwiththe
rules,whileBandCarealittlemoredifficult.Thethingis,yourenotalwaysgoingtobegivenastructure
withthe4thrankedsubstituentintheback.OnethingIseestudentsdoalotinthissituationistrytoredrawthe
structuretomakeiteasiertoassign(R)/(S)Whilethiscanbeeffective,itcaneasilyleadtomistakes.
Furthermore,whenyouredealingwithcyclicsystemslikemorphine[C],tryingtodrawthemirrorimageina
reasonabletimeframemightinducebraintrauma.[Bytheway,forB,yourememberwhytheCH2CH2Br
groupisranked3rd,right?[Note1]]
Insteadofredrawingthewholemolecule,justleavethehydrogen(orother4thrankedsubstituent)infrontand
figureoutwhetherthesubstituentsranked1,2,and3goclockwiseorcounterclockwise.Thentoggle(i.e.

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figureoutwhetherthesubstituentsranked1,2,and3goclockwiseorcounterclockwise.Thentoggle(i.e.
reversedirectionCWtoCCWorviceversa)toaccountforthefactthatthe4thrankedsubstituentisinthefront,
andassign(R)or(S)basedonthat.Youendupwiththesameanswerwithouthavingtoredrawanything.
Wealsomakethesetypesofadjustmentswhenwerelookinginmirrors.IfImlookinginamirroratyou
holdingoutyourrighthand,Iaccountforthemirrorbyflippingyourimagetoknowthatyouarereally
holdingoutyourleft.Itsthesamethingwithmolecules.

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Thistrickseemsobvious,butIvemetenoughpeoplewhodontdoittomakeitworthmentioning.
Determining(R)/(S)eventuallybecomessecondnature,asdoestheabilitytoflip,rotateandinvertchemical
structuresinyourhead.MuchlikeLondoncabdrivers,oneoftheinterestingsideeffectsofbecomingan
organicchemististhatithyperdevelopsyourbrainsspatialabilities.
[note1Priorityisdeterminedatthepointoffirstdifference.Hence,ofthetwocarbonsattachedtothe
stereocenters,CH2andC=O,theC=Oisgivenpriority[O>H],regardlesssofwhetherahigherrankedelement
isfurtherdownthesecondchain.]
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Taggedas:diastereomers,enantiomers,r/s,shortcuts,stereochemistry,tips
{9commentsreadthembeloworaddone}

mevans
James,
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SimpleTricksinOrganicChemistry:FiguringOutR/SMasterOrganicChemistry

James,

Callmecrazy,butthestereocenterinCshouldbeR,right?Somuchforsecondnature:P
Reply

James
Youarenotcrazy,Imanidiot.FixedThanksforthecorrection!
Reply

MichalSt
Isthereatrickforrotationswhenthehydrogen(orotherfourthrankedsubstituent)isintheplaneofthe
page?
Reply
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James
Click Here

Yepusethesingleswaprule(alater,improvedversionofthispost).
http://masterorganicchemistry.com/2011/01/24/thesingleswaprule/
Reply

PavelS.
HelloJames,
Thanksforthewonderfullyorganizedwebsite.Ihadaquestionabouttheswaptrick
Weweretoldtovisualizemoleculesinclassandthetrickisnevertaughteventhoughtheinstructoris
highlyratedandknowsit.Couldthisbebecauseitdoesnotworkinallcases?
H
|
CCl
WedgeOCH3HashCH3
TheaboveisjustsupposedtobeatetrahedralstructurewithHpointingupandClpointingright(bothare
intheplaneofthepage).OnthebottomleftisanOCH3withawedge(comingoutofpage)andaCH3
onthebottomrightwithahash(goingintopage).ThepriorityisCl>OCH3>CH3.ThisgivesS.
Accordingtotheswaprule,ifthehydrogenisnotpointingdownweswitchittoR,butthatwouldbe
wrongbecauseifyouuseamolecularmodelkitandorientthestructure,youhaveS.
AmIdoingsomethingwrongoristheRulenotahardsetruleandjustcorrect>90%ofthetime?
Reply

James
TheexampleIgavehasHinthefront.Ididntcoveranexamplewhereitisintheplaneofthe
page.
ThisisaVERYoldpost.AnevenbettertrickIfoundwastodothis:ifHisintheplaneofthe
page,doasingleswapofHwithwhatevergroupisadash.ThendetermineR/S.Whatevervalue
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page,doasingleswapofHwithwhatevergroupisadash.ThendetermineR/S.Whatevervalue
yougetwillbetheoppositeofthetrueR/S.Inyourexample,ifyouswapHwith(dashed)CH3,
andthendetermineR/S,itlookslikeR.Butsincewevedoneasingleswapitstheoppositeof
thatSinaccordancewithwhatyousay.
Relevantpost:
http://www.masterorganicchemistry.com/2011/01/24/thesingleswaprule/
Reply

PavelS.
Great.Thankyou!
Ishouldhavereadthesingleswaprulemorecarefully.Youveconfirmedformethatthe
R/Stogglemethodabovedoesntworkinallcases.Thesingleswaprulemakessenseand
ismoreuniversal.Thanksagain!
Reply
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Leisa

DoestheR/SChartyoumadeupthereworkallthetime?Igettheswapruleandwholeideabehindit,but
thischartmakeslifesomucheasier.
Reply

James
Betterpost:http://www.masterorganicchemistry.com/2011/01/24/thesingleswaprule/
Reply
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Imaginehavingacomprehensiveonlineguidetohelpyousolveyourownproblemsin
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SimpleTricksinOrganicChemistry:FiguringOutR/SMasterOrganicChemistry

ComparingtheSN1andSN2
ConvertingaFischerProjectionToALineDiagram
ConvertingaLineDiagramtoaFischerProjection
ConvertingaNewmanProjectiontoaLineDiagram
CurvedArrows

DeterminingR/SonaFischerProjection
E1withRearrangement
E1WithRearrangement(2)
EliminationExercise:ZaitsevsRule
EliminationReactionsinCyclohexanes
EliminationReactionsinCyclohexanes(2)
EvaluatingResonanceForms(1)Charges
EvaluatingResonanceForms(2)Octets
EvaluatingResonanceForms(3)NegativeCharge
EvaluatingResonanceForms(4)PositiveCharge
EvaluatingResonanceForms(5)Aromaticity
Exercise:CondensedFormula(1)
Exercise:CondensedFormula(2)
FactorsthataffectacidityAromaticity
FactorsThatAffectAcidity(1)ChargeDensity
FactorsThatAffectAcidity(2)Electronegativity
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FactorsThatAffectAcidity(3)Polarizability
Org 1 and Org 2
FactorsThatAffectAcidity(4)ElectronWithdrawingGroups
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FactorsThatAffectAcidity(4)Resonance
FactorsThatAffectAcidity(6)Orbitals
FormalCharge(1)AtomicCharge
FormalCharge(2)IntroductiontoFormalCharge
FormalChargeExercise:AllylCarbocation
FormalChargeExercise:CH2N2
FormalChargeExercise:CH3NO2
FormalChargeExercise:CN
FormalChargeExercise:CO3
FormalChargeExercise:HiddenHydrogens
FormalChargeExercise:HiddenLonePairs
FormalChargeExercise:N3
FormalChargeExercise:NH4
FormalChargeExercise:O3
FormalChargeExercise:RadicalsandCarbenes
HiddenHydrogens
HowFormalChargeCanMislead
HowHeatAffectsEliminationReactions
Howtodrawanenantiomer
HowToUseApKaTable
InSummary:Resonance
IntroductiontoElimination
IntroductiontopKa
IntroductiontoRearrangements
IntroductiontoResonance
IntroductiontotheE2Reaction
IntroductiontotheSN1:Experiments
IntroductiontotheSN2:Experiments
KeyPatternsinFormalCharge
LineDrawings
MakingOHIntoAGoodLeavingGroup
RearrangementReactions:AlkylShifts
Rearrangement:HydrideShift
Rearrangements:CarbocationStability
ResonanceCommonMistakes(1)
ResonanceCommonmistakes(2)
SN1Exercise:TheSubstrate

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SimpleTricksinOrganicChemistry:FiguringOutR/SMasterOrganicChemistry

SN1Exercise:TheSubstrate
SN1ReactionEnergyDiagram
SN1vs.SN2Overview
SN1WithAlkylShift(1)
SN1WithAlkylShift(2)

SN1WithHydrideShift
SN1:ApplyingtheSN1Reaction
SN1/SN2/E1/E2Substrate
SN1/SN2/E1/E2DecisionOverview
SN1/SN2/E1/E2DecisionSolvent
SN1/SN2/E1/E2DecisionTemperature
SN1/SN2/E1/E2DecisionTheNucleophile/Base
SN2Exercise:ApplytheSN2
SN2Exercise:LeavingGroups
SN2Exercise:TheSubstrate
SolventsinSN1andSN2Reactions
StereochemistryExercise1
StereochemistryExercise2
StereochemistryExercise3
StereochemistryExercise4
StereochemistryExercise5
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StrongandWeakAcids
Substitution:WhatisSubstitution?Org 1 and Org 2
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The4ComponentsofEveryAcidBaseReaction
TheE1Reaction
TheGoldenRuleofAcidBaseReactions
TheSingleSwapRule
TheSN1Mechanism
TheSN2Mechanism
TheSN2ReactionEnergyDiagram
UnderstandingR/SRelationships
UnequalResonanceForms
UsingElectronegativitytoFindReactiveSitesonaMolecule
WhatMakesAGoodLeavingGroup?
WhatMakesAGoodNucleophile?(1)
WhatMakesAGoodNucleophile?(2)
WhatMakesAGoodNucleophile?(3)
WhatsANucleophile?
ZaitsevsRule
YoureAlmostSubscribedToTheReactionGuide!

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