emi @ Types of Isomers @ Stereochemical Drawings @ Meo Compounds @nawman Prjections @Fischer Projections ® Cahn-Ingola- Prelag, Priosty. Rules @ stereochemical Terminology. @ Stereochemical Descriptors @ Stereochemical Description of Reackons @ Stereochemical Resolution of Enantiomers: e tt , Ashocats Tyeay Code: ATIEEoliw SKersochemistey. Tigges of isomers: 4 Copstiiuctionat. nave same. formuto ifPerent connecsiuity— Formuta: CsH, 0 2. Stereoisemers — nave same Pormuta & same connectvity ut ore NON~-Sup|rim posakle viaL retation in “apace. Now | (tee Re] aL 6 i Seve vs cast wae AA » H bans was ee of Formuta: C,Hsc2 Formuga:CyHO Formula: CsH\oCta cimpesaie — Nen-BLperimposawle Non- aperimposalole mirror vePlections Diostereomers Enantiomers Diastewomers Stereoisomers that ave mirror images = enantiomers iastereomers Stereoitomers that Ore not mirror Lenages = Stereochemica2 Drawings CRepresentations) vO ou Dash & Wedge Structures: af : “~ o—~ ox Yepresent atoms a fu lan ac CundePi ned) Dr QYBUPS Oriented towards the Observer represent atoms or Qroups oriented nay from ne observer Meso Compounds fe — Je iS Used ko Indicate Meso compounda have chiar trot te atom or a group centers ,Nowever, the motecete can be oriented w either iS net chivad CSuperim poses. with Aireckion. Often signifies the les own mirror rePlection) due to racemic mixture. SaN tne plane oP symmety: used dug to ambiguity —- - CTI plane oP eymmety, cg Aslusens Tyygi Sov Code: ATIEESeesaw Drawings Shows two atoms of interest wit dhw Meir swWostitients he pan these drawings are sometimes useRil bohen Grawin mechanioms reactions when the tation of groups is important tr, os Newman Prejections Shows two atoms of interest witn Meir swostituents “superimposed on top of each other. wae < “ on ——— @ LA™~ 2S w \ 4 Coser vation v cont atom Cot) point HCH, 4 Soap ae ator (circle) front atm ack atom ce User shortcut: when "tooking’ at the metecute Prom the Left , Wedges will Voe om the right ode of the nan, While the dashed a wi be on me sae of tie Newman, EE Looking at Me Melee from te right, the orientations witt be reverse. groups of interest Gk were &y echupsed conformations ig. ntercnay Bue to free can say cdouene sng conde anti Geurche. eclipsed Typ Lretotion) = 45" 3. Fischer Structures vi wsefr for Long-chain melecutes il muttiple chirog Cosyrmetric) atoms Vertical’ Lines Look aw: Novigonta® Lines Look ot you Code: ATIEECohn - neck —Prer Prony Rees Used +0 Assign stereschemical descriptors to molecules. @ Atom with the highec atomic number GL) has a hignec Priority RSCHN"H ; *O>*o Tf therés a tie, then you need to compare the next atom (s) connected Lower Priority due to Gs ere. fron Caan nections Ra cH cH, ve Ro CHa cH CH —cHs Sequence . M ul cHs AON Os OH / Q-c—cus R-coe en a Sy HOA Cvs C => 0 aifferen eo CoH ve HCH => Left ca of om Gy 4 the cest tre On! Centinug ang is is irreReyvant mel tet First cliffarencs found. @) Continue the Anaryss HU you Find the first aifPerence.. R= Chg OH CH Cag vs. Ro Che — CHa CH -SH CH, As MW 4 A HOH 4 2 wy Aes Rococo cn R- clo sy Hc OH WOR co# NS aR aH Lever 4 a ve cq Level 2: & ve CHH eh Level 3: CCH vs CH First Aifference gets Level 4: CHRHHH Vv scH front, Level 5: HAH vs HAE Aslasens Tyygi Sov Code: ATIEESterecchemicad Verminotogy alin On atom er a grexe of atoms, & a stereogenic center i me interchangs oP two suestituentS Attached to it AUCLES AO. New) ~“Sterevidomer Important! ~shereogenic canter i A dot in space Which May may net 62 An atom 1 ous \-\ these, ONO Molecetes Are. non- Superimprtatle ji } in space. & Nave The same. muta & connectivi \ J red aot = Se ee isa hereagenic. canter ChivaR Center —On atom with 4 aifferent substituents Cdoes net nave to Se carbon) OH ake H., Sterengenic. conter Ah cP buds we acne oxtem | 8 ‘ chivad atoms & & ster ie Stereogenic. canter, AR chirad centers Are stereagenic Conters tout on fome stereogenic centers are. Chirak centers Homochiral- bWO motecutes that have te same sense of Chivaging. ot their stereogenic center H OM On Q-2-butank CR)-2-Pentanse Cay" 3-hexanst. Heterochirag ~ Ewo molecutes that nave. a difPerent sense oP Chivakity. at their stereogenic center, eg. CRY-2eutank & CS\52-Pentanr® Homotopic. vs Enantictopic. vo Diasterectopic. Grup are tne two atoms or armups thot if excnomged with nypotheticar —K me at Qa time witt yield Q uw of Same moleceres , enantiomers , ot Aiasteveomers ei BE enantotogic Code: ATIEEStereochemicag Descriptors ohiw R&S — Letrahedrat atoms nigrest Erionity CIP Priority ruses C@-@?>@>@) oe “BOS oe GR Pn Cowest priori must £2 “owty" 2 ~hubrudiged atoms have prochirak Fas: Re & Siw oer, oe Tackeppnidic attack on Ws atom yietds KR oc tomer of the product. Ow S Cis & Trans — double bonds sc cyclic compounds Cis = mm te same side trans = on Me oeposite side tt H CH, CH. mS OC ox a X aN As cas ‘3 c BS cig He FH vane He cis trans E& 2 — double bonds E = trans Z=cs TUPAC enty Qtlows the use of cis/transS when the highest Cor Lowest) prion are te same or AeSerrbin) etic. Highec prion Higher prion compounds with two Buc ituents ar on thy Qroups on Oni Otherwise we must use G & 2 me side of Opovrite sides the C=C - oe Mme C=c.- Dw L — Fischer Projections Refers te Die last chiral carbon from tne top CHO cro | = D- Me higher prion rope Cer) mine ato HOT-H last chiro ey Ot the vight. WOH Ho-R L—the h (on) OF —the higher orion: rat -OH) on Me CHOKE nel ekoen Sooke eft Aslan Tyegy Sov Code: ATIEEErytnro & ‘hres — Fischer Ongjections alin Exythro — Same greup8 are on the same side of the motecute threo — Same Groups Are on the opposite sicdeo of che mdecute en & en er HR ®r _ Bm A Br Ph at ee = on = BER FH Ph ee Ph ee erythro knreo M& © —hericak descagters ¥ ctockwise, CP= ptus) CT. counter- crock wise, Pp -E ™“ - Cm= minus) Re Determination is { Y= Aone Looki “Ur I Enrough 2 Axis "Of crSeaeity TA Q moleewle “Spirats’ then M or P will depend on tne divection of Me spirad,e. 8 Counter ctockinie spirad a = ConPguration ee front ring. toack ving. Riyne.=Preteg System - based om the Newman projections , Aescrites & relative Positions OB groups A group Of interest > ° ¥ 3 KO™ sn Plane, ® NA Syn Penplanar wae ~ Gey =F inag G2 S Ainad aide ant lane Side |” oe <. @ i ‘ Sd Bide . . * ce ca ate, sn omti Periplanar side - AQ Periplanar Os, at Ts, 43 amti periplanar Wa of 7PM on Syn ctinak yy @ Vey L tron CY ant 4 <> Periglanar As AS Aslasens Tyygi Sov Code: ATIEEStereochemica® Cassification oP Reactens abu ioselectivity.— the ai. WH Ractivi various Sites Regioetecte ts Otel icccamse oe functions prone Examples: Py-cascn, RS, PN CHBr—cHs Markounikou Product — Hokegen attaches t> the, Nome Substituted atom A, 2h Mg%e A Diep Ko, Grignard ent atkacks the we wo Aesbophilic Sarbon 6 Me carbon rather ‘tran electrophilic. carben of Die alkene. Sterenseecificity.— one sberepizomer tne reactant gives feat & one Sterepisomer Se product , wae, the other one ayes aukpesent slerenigomer of Me product. Examples: awe mCPBA 9 2° A ar enantiomers {\Aiastereomers mn eh Pow sf ° A mCPBA, ° J diastereomers mh mh Dn Pn Sterecisomess of the wactant give afferent stereoisomers oP Me products => reaction is stereospecific « ‘Sterevsetectivity — Same starting materia produces two BC move Steresisomenc’ products, however , one or more of trese products is preferred Over Gre other Ones Syampe. Sharpless eporication -\- 9° G3“DST, Binge isomer an a product, HD TORY es the other enantiomer is not "euCOH Observed => reackon is Sterecselectve Steroselective. reactions can be Aiastereosetectve or enantiesetective based on the tereochemisty of re Pleduct. Aslasens Tyygi Sov Code: ATIEESumman, of Stereochemicag Rerationships oli Constitutionag Téomers — Completety different molecules Conformational Teomers — Same moetecetes that enty afer in BD-shape due tS Free rotation around single Gonds Enantiomers — non-Superimposaide. mirror © iS Have same physical & chemicar Properties UL Gchiral environment “Diastereomers — non-siperimposaide. NOn-mirror Lmages Have afferent Physica & chemicat Properti Meso Compounds — nen-chiyar Aue to the plane of symi however, have. oral ee geomet Compounds \: Same. moleadar formula 2. Different in some way Same connectivity 2 No Yes Constitutional Sterenisomers “somers S Different through rotations about single bSlds only ? Enantiomers, ingle bends only No Yes Ses Mirror _| Configurational Conformational No ae “Tages? Assmecs somers Diastereomers SKereochemicar Resotution oP Enantiomers Since enantiomers have identico® Shemicar & physicon DW AchiraQ envirsenment , tom 2 resolved oe either: A. Using Chirag, chromatogra 2. Ones Veversi Conveting them into ciasteceomers, Separating Owm usthg. physi means & converting tack inte Rial Ppgp SRI Code: ATIEE