Chem 350 Jasperse Ch. 3 Handouts 1
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1 Chem 350 Jsperse Ch. 3 nots 1 Strctre, Conformtions of Acyclic Alknes (3.7) A. Conformtions = Conformers = Rotmers = ifferent 3-D rrngements reslting from rottion ron single bon Norml zig-zg "swhorse" "Newmn Projection" B. Newmn Projections : look stright own one C-C bon If both bone crbons re tetrherl, there will be three bons extening from the front crbon, n three more bons extening from the bck crbon Terms: o Diherl ngle: ngle between bon on the front tom reltive to bon on the bck tom o Eclipse: when bons re ligne. 0º, 120º, 240º, 360º iherl ngles o Stggere: when bons re s fr prt s possible: 60º, 180º, 300º o Skew: nything else in between the eclipse n stggere extremes * * * * * * * * * 0º 60º 120º 180º 240º 300º eclipse stggere eclipse stggere eclipse stggere 360º eclipse Energy: Stggere best, eclipse worst Why: Torsionl strin. Replsion between boning electron pirs is rece in the stggere conformtion, n is worst in the eclipse conformtion. Rottion Brrier: energy gp between the best n worst conformtion when yo go throgh fll 360º rottion (s wol tke plce in fll bon rottion) Drw in Entergy igrm: 3 Reltive 2 Energy (kcl/mol) 1 Rottion Brrier 0 0º 60º 120º 180º 240º 300º 360º Diherl ngle
2 Chem 350 Jsperse Ch. 3 nots 2 Conformtions of Btne n Longer Alknes (3.8) C 3 C 2 -C 2 C 3 is more complex. Focs own C2-C3 bon. C 3 C C 3 3 C 3 C 3 C 3 C 3 3 C * C 3 0º 60º 120º 180º 240º 300º eclipse stggere eclipse stggere eclipse stggere Totlly Eclipse Gche C 3 3 C C 3 Eclipse Anti Eclipse Gche C 3 C 3 360º eclipse Totlly Eclipse Rottion Brrier 0 0º 60º 120º 180º 240º 300º 360º Diherl ngle Qestions 1. Drw the energy igrm 2. Wht wol be the rottion brrier? 6 kcl/mol Strin Energy Fctors: 1. Torsionl strin (why ll of the eclipse type conformtions re worse). Replsion between bone electrons 2. Steric strin: When toms themselves get too close. Atom-tom replsion. 3. Angle strin: When bon ngles cn t chieve iel VSEPR ngles. (No ngle strin in ethne or btne) Totl Strin = Torsionl strin (re ny bons eclipse?) + Steric strin (re ny toms too close) + Angle strin (re ny bon ngles force to be other thn iel?) Qestions 1. In generl, why re stggere better thn eclipse? Torsionl strin. 2. Why is eclipse better thn totlly eclipse? Both hve eclipsing n torsionl strin. Bt the totlly eclipse conformtion s on severe steric strin. 3. Why is nti better thn gche? Both re stggere, so neither hs ny eclipsing or ny torsionl strin. Bt the gche hs little bit of steric strin. 4. Why is gche better thn eclipse? Gche is stggere, with no torsionl strin. Eclipse is worse becse of eclipsing/torsionl strin. Pls the steric strin is big worse. 5. Why is nti better thn totlly eclipse? Both torsionl strin n severe steric strin mke the totlly eclipse wy worse.
3 Chem 350 Jsperse Ch. 3 nots 3 Smmry 1. Anti < gche < eclipse < totlly eclipse 2. Steric n torsionl resons 3. The blkier sbstitent, the greter the steric strin in eclipse n totlly eclipse conformtions Skills. Be Able to: 1. preict reltive rottion brriers 2. write conformtionl nlysis (rottion/energy igrm) 3. rw Newmn pictres for ny bon in ny strctre 4. ientify nti/gche/eclipse/totlly eclipse conformtions Steps to Drwing Newmn Strctre: 1. Drw circle (bck crbon) with ot in the mile 2. A three sticks extening from the periphery of the circle, with one of them stright p 3. A three sticks extening from the center ot (front crbon) to illstrte the bons riting from the front crbon C 3 C 3 C 3 Problems 1. Rnk the rottion brriers for the following, reltive to the inicte bons C 3 -C 3 They increse from left to right. The rottion brrier is bsiclly ominte by how b things re in the worst possible, totlly eclipse conformtion reltive to bon, n the steric interction involve. From left to right, the worst eclipsing is between: n ; C 3 n ; C 3 n C 3 ; C 3 n isopropyl; C 3 n t-btyl 2. Drw Newmn projections for the best n worst conformtions of the strctre shown, reltive to the inicte bon. Use the 3 r crbon in the bck. C 3 C 3 C 3 best stggere C 3 C 3 C 3 worst totlly eclipse
4 Chem 350 Jsperse Ch. 3 nots 4 Ring Stbility n Ring Strin (Section 3.12) Ring Size Totl Ring Strin (kcl/mol) Strin Per C 2 Min Sorce Of Strin Angle Strin Angle Strin Torsionl Strin (eclipsing) STRAIN FREE Torsionl Strin (eclipsing) Torsionl Strin (eclipsing)
5 Chem 350 Jsperse Ch. 3 nots 5 Strctrl Isomer Problems Check forml first. Is it n cyclic molecle, or not? (Cyclic lkne or n lkene or something ) Be systemtic. Try the longest possible chin (or lrgest ring size) first, then systemticlly shorten it n fin the brnche isomers. Avoi plictes! Bewre of things tht look ifferent bt re relly the sme thing. 1. Drw ll strctrl isomers of C (Be systemtic; no plictes!) Forml proves cyclic lkne Drw ll strctrl isomers of C (Be systemtic; no plictes!) Forml proves either cyclic lkne or n lkene. In ition to the 27 cyclolknes shown, there re t lest nother cople ozen lkenes. Notice tht these re 27 cyclolkne strctre isomers; mny of them col lso hve cis/trns isses, so where I rew jst one, yo col perhps ctlly rw both cis version n trns version. Cyclic C 7 14
6 Chem 350 Jsperse Ch. 3 nots 6 Cyclohexne Chir Conformtions (Section 3-13,14) Cyclohexne hs no ngle strin or torsionl strin Cyclohexne hs perfect 109º ngles with stggere, non-eclipse C-C bons Obviosly it is not flt (ntrl ngle for flt cyclohexne wol be 120º) Chir Conformtions: A B C D best esier to see "chir" E bot intermeite o Chirs A n B re constntly interconverting vi bot E o A n B re best to rw n work with. o Bt C/D mke it esier to vislize why it s clle chir : 4 crbons mke the set of the chir, one mkes bckrest, one footrest. Process for Drwing Both Chirs: "Right-hne chir" "Left-hne chir" 1. Drw 4-crbon zig-zg. It helps if yor left-most crbon is little lower thn yor 3 r crbon 2. A 5 th crbon n 6 th crbon, bt on t hve them exctly nerneth the 2 n n 3 r crbons. 3. Connect the 6 th crbon to the orginl 1 st crbon For left-hne chir, strt p n zig-zg own.
7 Chem 350 Jsperse Ch. 3 nots 7 Axil n Eqtoril Positions for Sbstitents xil: 3 verticl p 3 verticl own e e e e e e eqtoril: 6 essentilly horizontl "ppers" n "owners" 1. Ech crbon hs one xil n one eqtoril s 2. Alwys hve six xil ttchments 3. 3 xils p (on lternting crbons) 4. 3 xils own (on lternting crbons) 5. Alwys hve six eqtoril ttchments 6. For processing cis/trns problems, it s helpfl to recognize pper from owner positions 7. When chir flips, wht ws eqtoril becomes xil, n wht ws xil becomes eqtoril * chir flip * Drwing eqtoril n xil bons: Mke xil stright p or stright own (3 ech) Mke eqtoril bon lines lmost exctly horizontl Eqtorils re esiest to rw on left n right-most crbons Drwing Mono- n DiSbstitte Cyclohexnes (Sections 3-14,15) Alwys ttch the first sbstitent onto the leftmost crbon (esiest to rw) 3 C * Eqtoril: More stble chir flip * C 3 Axil: Less Stble Drw in the on ny sbstitte crbon, bt skip on -only crbons Eqtoril is better thn xil for steric resons. In the xil configrtion, the sbstitent hs estbilizing steric interctions o 2 extr gche interctions, n 1,3-ixil interctions For isbstitte chirs, let the cis/trns reltionship gie whether the secon sbstitent shol be in n pper or lower position reltive to the originl sbstitent. If one sbstitent is bigger thn the other, the most stble chir will lwys hve the lrger sbstitent eqtoril
8 Chem 350 Jsperse Ch. 3 nots 8 Cis n Trns Disbstitte Cyclohexnes Qestions: 1. Drw both chir forms for cis-2-methyl-1-isopropylcyclohexne. 2. Which is the best chir for cis-2-methyl-1-isopropylcyclohexne? 3. Drw both chir forms n ientify the best chir for trns-2-methyl-1- isopropylcyclohexne. 4. Which is more stble, cis- or trns-2-methyl-1-isopropylcyclohexne? 5. Then nswer the sme qestions for the 1,3- n 1,4- isomers. 1,2- DiSbbe C 3 C 3 cis-1 Best cis is A > B Best trns is C > D Best of ll is C (eq-eq), so trns-1 is better thn cis-1 C 3 3 C 3 C A B trns-1 C C 3 A > B n C > D becse lrge isopropyl grop wnts to be eqtoril D 1,3- DiSbbe C 3 cis-2 trns-2 C 3 A C C 3 3 Best cis is A (eq eq) > B (x x) Best trns is C (eq x) > D (x eq) Best of ll is A (eq-eq), so cis-2 is better thn trns-2 B C 3 C 3 C D 1,4- DiSbbe C 3 cis-3 trns-3 C 3 C 3 A Best cis is A (eq x) > B (x eq) Best trns is C (eq eq) > D (x x) Best of ll is C (eq-eq), so trns-3 is better thn cis-3 B C 3 C 3 C D C 3
9 Chem 350 Jsperse Ch. 3 nots 9
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