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STEREOCHEMISTRY HOPEFULLY MADE SIMPLER

Stereoisomersmoleculesthathavethesameconstitution,butdifferentdispositionof
groupsinspace.Inotherwordstheatomsareconnectedtoeachotherinthe
same way, they only differ with respect to relative orientation in three
dimensionalspace.
ChiralGeneral DefinitionAny object that is not superimposable on its mirror
image.Yourhandsarechiral,thatiswhyyouneedtwodifferentleathergloves,
onethatonlyfitsyourrighthand,andonethatonlyfitsyourlefthand.Ifyour
handsweresuperimposable,thenyouwouldonlyneedonekindofgloveandit
wouldfitbothhands.
ChiralChemistry Definition; AtomAny tetrahedral carbon atom that has four
differentsubstituentsisachiralcenter.Anytetrahedralcarbonatomthathas
fourdifferentsubstituentsisachiralcenter(itwasworthrepeating).Thisisa
simpleconsequenceofgeometry;therearetwodifferentwaystoplacefour
differentsubstituentsinatetrahedralarrangement.Lookingforfourdifferent
substituents on a single carbon atom is the easiest way to identify a chiral
molecule.Itisworthmentioningthatachiralcenterisaspecialtypeofamore
generalsituationcalledastereocenter.Astereocenterisanyatominamolecule
forwhichexchangingtwogroupscreatesadifferentstereoisomer.Allchiral
centersarestereocenters,however,notallstereocentersarechiralcentersaswe
willencounterexamplesofthisinlaterchapters.Donotsweatthisdetailatthis
point.Thebottomlineisthatwhenyouhaveatetrahedralcarbonatomwithfour
differentgroups,callitachiralcenterandlifewillbegood.

Asafurtherconsequenceofsimplegeometry,thereareonlytwodifferent
waystoplacefoursubstituentsaroundachiralcenter,andasshownabovethe
resultingtwo differentmoleculesaremirrorimages ofeach other.Theyare
nonsuperimposablemirrorimagesofeachother.Youshouldmakemodelsof
the above molecules and prove to yourself they are different and non
superimposableifyouhaven'tdonethisalready.Thispairofchiralmolecules
thataremirrorimagesofeachotherarecalledenantiomers,achemistryname
given to represent this special mirror image relationship between different
molecules.
Acarbonatomisnot
achiralcenterifeventwoofthesubstituentsarethesame.A
carbonatomisnotachiralcenterifeventwoofthesubstituentsarethesame(thatwas

Enantiomers and Diasteromers - Molecules


With Two Stereocenters

These structures match the structures in the back of the web handout on stereochemistry, so you
should refer to that. This molecule, 2,3-dihydroxybutanoic acid, has two stereocenters (one at
carbon 2, and one at carbon 3, so there are four possible stereoisomers. The 2R,3R and 2S,3S
stereoisomers are enantiomers of each other, and the 2R,3S and 2S,3R are enantiomers of each
other. These are enantiomer pairs becuase they are nonsuperimposable mirror images of each
other. Any other pair, such as 2R,3R and 2S,3R, are diastereomers of each other, since they are
stereoisomers that are not enantiomers (not mirror images of each other). Thus, you use the
terms "enantiomers" or "diastereomers" to describe the stereochemical relationship when
comparing different stereoisomers