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Topic 2c

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Chemistry 2223B
Felix Lee

.3 C2 (chiral centre), ,3and CH stereocentre , a type of stereoisomer. estern Universityuperimposable on their mirror not all 2012 enantmmolrcule is asobboCu,CtH.Houercfebent#2 is oThe tooheirorsmcomesonfschrorbufchialey in a so they areAn example would be plthei-hsoompetyane.A Chemry23aiA .c.OirgaonfichSrtltcatnreRv/3C:Chfrualiyionhiral (non-chiral) objects have a  4 3 E/Z 1 S 2 Organic Structure #3: Chirality .  4 2 1 3 R 3 OCH 3 H  CH Cl S R Sonvention to specify the absolute 3D configuration of R ClocCounterclockwise= plane. pr(rt)gnrdoh(n1thothied-eghned We useThe convention assigns a priority order to the substituents on the stereocentre   3  : S or R 3 Organic Structure #3: Chirality CH 2 N H H CH H -methylindole N O HO ( )- = 3 H OH C2 C C CH 3 O H C2 = HCH 3 H OH C2 O C C CH O ( )-2-ethylcyclohexFischer projection Determine whether the stereocentre in each of the following is 4  N Organic StructHre #33 Chirality N CH Cl H 3 H Cl CH H Cl H 3 CH stereoisomer? E,R H H H H Cl 3 Cl3 H CH N N H Which one of the following is an  OH  OH OH  H OH OH H H 2 C S R CH Organic StructureO#3: Chirality O HO H H OH H OH 2 C R S CH O H HO H H H O2 B CD C CH S S O HO HO H OH OH OH2 A C CH R R O H H D-erythrose L-erythrose Many molAecexaMhplecmfsuwttanwolstuleic2ntrte.iiheoeemauacxll,swing the B. olecule s withTwo or More Stereocentres 6  ? D & B , or Organic Structure #3: Chirality ). & D B and D or C A ) or ( B , or C and & A A . n theoretical maximum. diastereomers enantiomers of each other. not Diastereomers are compounds that are stereoisomers of each other, but o These are calledntoreesr,havstreoifersnt(veeytlenssonnirieriec TheHow about tThe easiest way to distinguienolntoleewsahnwdoiorero  compounds. Organic Structure plnemmfetryty meso OH OH COOH COOH H H H OH COOH COOH . HO H meso OH H it is achiral. Achiral compounds containing two or more A B COO H COOH H i.e. HO meso A andandiraereanisterromers, as are B and C
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