8/25/2016

HowtodrawenantiomersusingtheSingleSwapRuleMasterOrganicChemistry

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TheSingleSwapRule
byJames
inAlcohols,OrganicChemStudyTips,OrganicChemistry1,Stereochemistry,StereochemistryCC
Idontthinktherearethatmanytrickstodoingwellinorganicchemistry,butthereareafew.Iwaskindof
surprisedlastmonthwhenItalkedtoanumberofstudentswhohadntevercomeacrosstodaystrick,whichis
probablythemostusefulofthemall.IusedtocallittheR/Stogglebutamuchbetternameforitcomesfrom
Steven,whocallsittheSingleSwapRule.
Hereshowitworks.Takeamoleculewithastereocenter,like(S)2butanol(drawnbelow).IfyouswapANY
TWOsubstituents,youwillinverttheconfigurationofthestereocenter.Thatis,switchinganytwo
substituentswillgiveyou(R)2butanol.
Therearesixpossiblewaysyoucoulddothis,andtheyrealldepictedbelow.
Bytheway,donttakemywordforitifyoucantseethis,demonstratetoyourselfthateachofthesesix
moleculesis(R)2butanol.

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TheSingleSwapRulecomesinhandyfortwosituationsinparticular.
1.Determiningwhetherastereocenteris(R)or(S)
2.Whenyouneedtodrawtheenantiomerofastereocenterlikewhenyouaredrawingtheproductofan
SN2reactionforinstance.
Thefirstorderofbusinessindeterminingwhetherastereocenteris(R)or(S)istonumberthepriorityofthe
substituentsaccordingtotheirpriorities.Imnotgoingtotalkabouthowtodothistoday,althoughthereare
plentyofgreatresourcesonhowtodosoifyoudliketopracticethisessentialskill.Accordingtotherules,
onceyouveorderedthesubstituents,youneedtoputthe4thrankedsubstituentinthebackandthendetermine
whetherthe1st,2nd,and3rdrankedsubstituentstraceaclockwiseorcounterclockwisepath.Inpractice,few
peoplefollowthistotheletter.Thatsbecauseyoustillgetthesameresultifthe4thrankedsubstituentis
connectedtoadashedbond.

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Theupshotofthisisthatdetermining(R)/(S)isfairlystraightforwardaslongasthe4thrankedsubstituentis
dashed.Butwhatifyourexaminerunhelpfullydrawsthe4thrankedsubstituentasawedge,orevenofftoone
side?
ThatswheretheSingleSwaprulecomesinhandy.
Letssayweregiventhismolecule.Notethatpriority#4ispointingoutinfront.Insteadofredrawingthe
wholemoleculetodepictitsuchthat#4isintheback,wecannowbustoutthistrick.Switchthe#4substituent
withwhateverisintheback.Sinceweredoingasingleswap,weregoingto*invert*thestereochemistryfrom
(R)to(S)orviceversa.Nowsincethe#4isintheback,wecaneasilydetermine(R)/(S)andhere,its(R).
Sincewedidasingleswap,thatmeansthatouroriginalstereocentermusthavebeen(S).
Whatif#4ispointingofftotheside?Samething.Swapitwithwhateversintheback.Thiswillinvertthe
stereochemistry.Soagain,whenwedetermine(R)/(S),werememberthatouroriginalstereocenterwillbethe
opposite.

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Drawingtheenantiomericconfigurationatastereocenter.
TheSingleSwapRulealsocomesinhandywhenyouneedtoshowthatastereocenterhasgonethrough
inversionofconfiguration.IfyouvestudiedtheSN2reaction,youknowthatduetothebacksideattack,this
reactionproceedswithinversion.ButIveseenlotsofstudentsgetconfusedwhenitcomestimetoactually
drawtheproducts.Thesingleswaprulemakesiteasier.Heresanexampleofwhatnottodoandalsoaway
tosystematicallyapplytheSingleSwapruleinordertobeabletoreliablydrawinversionofconfiguration.

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Dothis1)drawyourstartingmaterial.2)doasingleswap.thiswillinvertthestereocenter.3)replaceyour
leavinggroupwithyournucleophile.Thatsit.YouvenowshownanSN2withinversionofconfiguration.
TheSingleSwapalsoworksforFischerprojections,Newmans,younameitthisiswhy,Ihastentonote,you
arentallowedtoflipanytwoatomsonaFischeryouendupgettingtheoppositeconfiguration.

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Org 1 and Org 2
Withpracticeyoullendupdoingthisinyourheadjustfigureoutthepriorities,tracethepathof1,2,and3,
Click Here
andif#4isinthefrontorontheside,rememberthatitstheoppositeofwhateveryouget(because#4isinthe

front).ItsprobablythemostusefultrickthereisinOrg1,andIstilluseitalmosteverysingleday.
HeresavideoshowingtheSingleSwapRuleinaction.

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Taggedas:diastereomers,drawing,enantiomers,r/s,shortcuts,singleswap,stereocenters,tips,tricks
{14commentsreadthembeloworaddone}

Zach
Ijustlearnedanothertrickbyusingmyhands.Apparently,youcanpointyourthumbofonehandinthe
directionofthe4thprioritygroup(thatmeanspointitintothepageifthatswherethe4thgroupisgoing),
andwhicheverhandsfingersrollinthedirectionofthe1,2,3priorities(lefthandisS,righthandisR)is
thewinner.Thisseemstoworkevenifthe4thpriorityispointingoutofthepage,oracrossit.Hopethats
clear!
Reply

james
Preparing for Organic? Get an instant set of awesome "cheat sheets" for

Interesting.Imgettingittoworkinmostsituations,butnotall.Forinstancecheckthefirst
Org 1 and Org 2
diagram,secondrow,exampleontheleft.UsingthatmethodIgetS.Whataboutyou?
Click Here
Reply

Cara
ThehandruleisalsowhatIlearned,andImprettysureitalwaysworks.Afterreadingyour
commentIwentbacktoallofthemoleculesonthispageandcheckedtheyallagreewith
thehandtrick,soImnotsureoftheproblemyourehaving.Thehandrulerequiresyouto
picturethemoleculein3Dandrotateyourfingersthatway,ratherthanjustlookingat
clockwise/counterclockwise.Itsneverfailedme.ItshowIknowifIverotatedmolecules
correctlyornotwhendoingproblems.Superhelpful,inmyopinion.
Reply

Lara
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WOWINEVERKNEWTHIS!!SOOOHELPFUL!
Reply

stundt
Thanksalotinevernewabtswaprule
Reply

collethamkusu
THANKSITSWASDIFFICULTTOMETOUNDERSTANDBUTNOWIDID.
Reply

Stef
Ithinkyoujustsavedmylife!
Reply

Katy
Dothestereochemistryinvertforacid/basereactionsoronlySN2?
Reply

James
JustforSN2.
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Reply

Org 1 and Org 2

Click Here

Kumar
Ihadadoubtinthesecondmoleculehere
http://chemwiki.ucdavis.edu/@api/deki/files/1538/newest_problems.JPG?
size=bestfit&width=392&height=315&revision=1
Beforetheswap,itwasS.HydrogenshouldbeatthebackinsteadofBromine.Evenafter
rotating/swappingbetweenHandBr,IamgettinganS(CCW).EveninthesitefromwhichIsawthis
problem,saysitsanR.WhatamIdoingwrong?
Reply

AlyxVance
FantasticpostasalwaysJames!!Justafewcorrectionsneededinmyopinions.
Ithinkyourassignmentsofthestereocentersforthetwotartaricacidmoleculeswerewrong.Ihavetried
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Ithinkyourassignmentsofthestereocentersforthetwotartaricacidmoleculeswerewrong.Ihavetried
toconvertthedrawingstolinewedgediagramsandfoundoutthatyour(R,R)moleculeshouldbe(S,S)
instead!
TheReuschtextbookalsoseemstoimplythesame:
https://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/sterism3.htm
CorrectmeifIamwrong.Thanksforyourgreatcontent!!
Reply

James
Shoot.Youarecorrect.Letmefixthis.
Reply

AlyxVance
IalsojustnoticedthattheNewmanprojectionmoleculeontheleft(justtotherightofthe
twotartaricacidmolecules)shouldhaveSconfigurationinstead!WhenIconvertedthe
Newmanprojectiontolinewedgedrawing,theHisonawedge,whileOHisonadashed
bond.SoIthinkthattherealconfigurationshouldbereversedtoS!
Reply

James
Fixed.Thanksforlettingmeknow.
Reply
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AdditionofHCltoalkynestwicetogivegeminaldichlorides
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PointersonFreeRadicalReactions
ProtectingGroups
ProtectingGroups
ProtonTransfer
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Puttingittogether(1)
Org 1 and Org 2
Puttingittogether(2)
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Puttingittogether(3)
PuttingtheNewmanintoACTION
ReactionMaps
Rearrangements
RecognizingEndoandExo
Redraw/Modify
ReturnofTheSN2
RobinsonAnnulation
RobinsonAnnulationMech
SecondMostImportantReactionsofAlkynes:LindlarNa/NH3
SigmaandPiBonding
SN1vsSN2
sn1/sn2PuttingItTogether
sn1/sn2/e1/e2Exceptions
sn1/sn2/e1/e2Nucleophile
sn1/sn2/e1/e2Solvent
sn1/sn2/e1/e2Substrate
sn1/sn2/e1/e2Temperature
Stereochemistry

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Stereochemistry
StrongAcidStrongBase
StrongAndWeakOxidants
StrongandWeakReductants
StrongerDonorWins

Substitution
Sugars(2)
Synthesis(1)WhatsDifferent?
Synthesis(2)WhatReactions?
Synthesis(3)FiguringOutTheOrder
SynthesisPart1
SynthesisStudyBuddy
Synthesis:WalkthroughofASampleProblem
Synthesis:WorkingBackwards
tbutyl
Tautomerism
TheAwesomenessOfTheSN2
TheClaisenCondensation
TheE1Reaction
TheInflectionPoint
TheMesoTrap
TheMichaelReaction
TheNucleophileAddsTwice(totheester)
TheOneSentenceSummaryOfChemistry
TheSecondMostImportantCarbonylMechanism
TheSingleSwapRule
TheSN1Reaction
TheSN2Reaction
TheWittigReaction
ThreeExamTips
TipsOnBuildingMolecularOrbitals
Top10Skills
TryTheAcidBaseReactionFirst
TwoKeyReactionsofEnolates
Welcome
Whatmakesagoodleavinggroup?
WhatMakesAGoodNucleophile?
WhattoexpectinOrg2
WorkBackwards
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ZaitsevsRule
Org 1 and Org 2
TuesdayOct22AcidBaseWebinarat9pmEST
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Videos
ASimpleTrickForDeterminingR/S
ApplyingE2ReactionswithNewmanProjections
BondRotations:Exercise1
BondRotations:Exercise2
BondRotations:Exercise3
BondRotations:Exercise4
BondRotations:Exercise5
BondRotations:TheSteeringWheelAnalogy
BronstedandLewisAcidity
BulkyBasesinEliminationReactions
CarbocationStability
ComparingE1andE2Mechanisms
ComparingE1andE2Stereochemistry
ComparingtheE1andSN1
ComparingtheSN1andSN2
ConvertingaFischerProjectionToALineDiagram
ConvertingaLineDiagramtoaFischerProjection
ConvertingaNewmanProjectiontoaLineDiagram

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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
FactorsThatAffectAcidity(3)Polarizability
FactorsThatAffectAcidity(4)ElectronWithdrawingGroups
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
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HowToUseApKaTable
Org 1 and Org 2
InSummary:Resonance
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IntroductiontoElimination
IntroductiontopKa
IntroductiontoRearrangements
IntroductiontoResonance
IntroductiontotheE2Reaction
IntroductiontotheSN1:Experiments
IntroductiontotheSN2:Experiments
KeyPatternsinFormalCharge
LineDrawings
MakingOHIntoAGoodLeavingGroup
RearrangementReactions:AlkylShifts
Rearrangement:HydrideShift
Rearrangements:CarbocationStability
ResonanceCommonMistakes(1)
ResonanceCommonmistakes(2)
SN1Exercise:TheSubstrate
SN1ReactionEnergyDiagram
SN1vs.SN2Overview
SN1WithAlkylShift(1)

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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
StrongandWeakAcids
Substitution:WhatisSubstitution?
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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Org 1 and Org 2
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