11/18/2016 Stereoisomerism

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REVIEW OF CONCEPTS AND VOCABULARY

SECTION5.1
Constitutionalisomershavethesamemolecularformulabutdifferintheirconnectivityofatoms.
Stereoisomershavethesameconnectivityofatomsbutdifferintheirspatialarrangement.Thetermscisandtransare
usedtodifferentiatestereoisomericalkenesaswellasdisubstitutedcycloalkanes.

SECTION5.2
Chiralobjectsarenotsuperimposableontheirmirrorimages.
Themostcommonsourceofmolecularchiralityisthepresenceofachiralitycenter,acarbonatombearingfour
differentgroups.
Acompoundwithonechiralitycenterwillhaveonenonsuperimposablemirrorimage,calleditsenantiomer.

SECTION5.3
TheCahnIngoldPrelogsystemisusedtoassigntheconfigurationofachiralitycenter.Thefourgroupsareeach
assignedapriority,basedonatomicnumber,andthemoleculeisthenrotatedintoaperspectiveinwhichthefourth
priorityisonadash.Aclockwisesequenceof123isdesignatedasR,whileacounterclockwisesequenceis
designatedasS.

SECTION5.4
Apolarimeterisadeviceusedtomeasuretheabilityofchiralorganiccompoundstorotatetheplaneofplane
polarizedlight.Suchcompoundsaresaidtobeopticallyactive.Compoundsthatdonotrotateplanepolarizedlight
aresaidtobeopticallyinactive.
Enantiomersrotateplanepolarizedlightinequalamountsbutinoppositedirections.Thespecificrotationofa
substanceisaphysicalproperty.Itisdeterminedexperimentallybymeasuringtheobservedrotationanddividingby
theconcentrationofthesolutionandthepathlength.
Compoundsexhibitingapositiverotation aresaidtobedextrorotatory,whilecompoundsexhibitinganegative
rotation aresaidtobelevorotatory.
Asolutioncontainingasingleenantiomerisopticallypure,whileasolutioncontainingequalamountsofboth
enantiomersiscalledaracemicmixture.
Asolutioncontainingapairofenantiomersinunequalamountsisdescribedintermsofenantiomericexcess.

SECTION5.5
Foracompoundwithmultiplechiralitycenters,afamilyofstereoisomersexists.Eachstereoisomerwillhaveatmost
oneenantiomer,withtheremainingmembersofthefamilybeingdiastereomers.
Thenumberofstereoisomersofacompoundcanbenolargerthan ,where thenumberofchiralitycenters.
Enantiomersaremirrorimages.Diastereomersarenotmirrorimages.

SECTION5.6
Therearetwokindsofsymmetry:rotationalsymmetryandreflectionalsymmetry.
Thepresenceorabsenceofanaxisofsymmetry(rotationalsymmetry)isirrelevant.
Acompoundthatpossessesaplaneofsymmetrywillbeachiral.
Acompoundthatlacksaplaneofsymmetrywillmostlikelybechiral(althoughtherearerareexceptions,whichcan
mostlybeignoredforourpurposes).

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11/18/2016 Stereoisomerism

Amesocompoundcontainsmultiplechiralitycentersbutisneverthelessachiral,becauseitpossessesreflectional
symmetry.Afamilyofstereoisomerscontainingamesocompoundwillhavefewerthan stereoisomers.

SECTION5.7
Fischerprojectionsaredrawingsthatconveytheconfigurationsofchiralitycenters,withouttheuseofwedgesand
dashes.Allhorizontallinesareunderstoodtobewedges(comingoutofthepage)andallverticallinesareunderstood
tobedashes(goingbehindthepage).

SECTION5.8
Somecompounds,suchasbutaneand(cis)1,2dimethylcyclohexane,canadoptenantiomericconformations.These
compoundsareopticallyinactivebecausetheenantiomericconformationsareinequilibrium.

SECTION5.9
Resolution(separation)ofenantiomerscanbeaccomplishedinanumberofways,includingtheuseofchiral
resolvingagentsandchiralcolumnchromatography.

Copyright2015JohnWiley&Sons,Inc.Allrightsreserved.

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