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by: Michelle Gulgowski DVM


Marketplace > University of Kentucky > Chemistry > CHE 230 > ORGANIC CHEMISTRY I
Michelle Gulgowski DVM
GPA 3.91


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This 16 page Class Notes was uploaded by Michelle Gulgowski DVM on Friday October 23, 2015. The Class Notes belongs to CHE 230 at University of Kentucky taught by Staff in Fall. Since its upload, it has received 40 views. For similar materials see /class/228298/che-230-university-of-kentucky in Chemistry at University of Kentucky.




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Date Created: 10/23/15
5 sterenehemistry and Cnnfnrmalinnal Analysis nf Rings 51 Sumary of Ixomerixm m far TWD cumuuunds that have dentma furmu ae but are hat dentma enher m sha e Dr ehmne are caHed rmmers learners can be 53 e mg i i m E y e h weseem e b we have an Eum atera t a u e an the dea band anmes er m9 are fumed m defurm te anmes er an We wemd expect that the weum makethe eempeuhd h uher m energy In fact rt dues The extra energy 5 sad te be due te ange straw We can eehuhue up the adder te evemhutahe e empehtahe and the We Fur e DDWQDH er h srdes the dea ang ew v s ca w ated m be IEEI e 35UH The ca w ated band anmes e shnwnfnr DDWQDHSfrDm ama g e m a deeeeeh x 7 4 91 5 L35 L2 3 m a MD r e 120 10 L44 We wemd guess rrerh thrs tame that the Evdua kane wrth the East EHQ E seam wemd be evempehtahe and that the amuunt er anu e straw m a cumunund waam steadW rnaraasa after that ans was ma tnaarv Drnunsed bv Adu f van Saver m was In fact van ver s ar nat 2 bn c ands m urder ta rmmrmze tnarr anaruv We can acmaHv ca w ate ma arnaant arnng szrarn m varmus Evdna kanes bv bumer tnarn wrtn 02 rnaasanna ma a aunt ar ergv rawaasad and cumuanng tnrs anarav wrtn tna arnaant ar anerav rawaasaa bv an acvch a kane WE get a tab ethat aaks hkethequnwmg mr mu ma um Fm mm mm n mu a r n 4 20 3 12 1 s quot n a r r n w m x Tna nna straw starts verv nan raaanas zara wan Evdnhexana rnaraasas 595m ta a aaa mawmum at Evdununana and tnan decreases ta raaan zara 595m wrtn Evchjt tradecane Whv an we nbserve ans aattarn7 We have a readv 52m tnat smaH nnas have a canswderab e arnaant ar anu e straw Tnara are twu atnar saaraas ar straw tnat arE passrma m wan aampa M15 1 s aw m ma acvch a kawes Evcma kanes can axpananaatarsranaw straw a stan straw rr an rn a anmes are u staQQErEd and r nan undmg araaas are fumed ta aarna c nse ta aaan 2r rn Da 2 Tnsna rarnr r aass s arstr r mn r m and stana str In fa strarnr nas 5M kn rns v w n Ermaan a nnu ana ar ma 7c Ends 2 2 tn ma 44 bands are panaatw echused Tnas cvcmurnuane m addmun ta rts anu e straw na at ar tarsrana straw Tna anu e straw s sa bad tnat ma twu su n a m Evdnu DDan r nrbwta s makmg up t 2 and dun t rnaat headrnn satnattna bands are bent banana bands Janas Fm 53 As a resmt Evduuruuane rs rh uch rh cre reach v2 thah rh cst cvd us k ahes H Cvdubutana ah the dther hand puckers a htt e tut Thts makes the hand a u es srhaHer than the D anar anme at an ncreasmg the anme straw put I reheves a mt cr mrsmna Straw the haw W the puckered ccrtcrrhattch pr Evdubutane there are twn dttrerert kmds cr CrH hand and hence twu dttrerert kmds cr H atcrh H hands that are hearh arm tc dther CrH hands and there are thcse 44 hands that are hearw arm tc C W see that thts has dreat S Qm canca fur EVE DHEXEHE rmds Cvdnuentane was Dram have an 2 av he we 3 3 i2 0 am h resmtr ts an t cr tcr a ds As cvdnuentane adapts a puckered cchrcrrhauch Thts ncrEaSES 9 2 Straw a ht e tut p t reheves a mt cr the tnrsmna strath There are twc puckered ccrtcrrhattchs cr EVdDDEntanE che m Whmh at e u tnrsmna straw and DmDDunds wtth vermembered rmds tehd tc react m wavs that decrease the tnrsmna straw t e bv canvemng ah su rhvbndwzed c atcrh m the rmd mm ah SDZVandtzed atcm 2321 42 t a apteotl WW sububse the dt erert c atcrns tn the rtne are nDnrtdEnuca t e have dt erert subsutuents Haw dB we knDW whtch c atcrn tn cvctcbentane wttt pucke The answer tsthat we wuutd have tc tuck atthe dtfferent enerctes ct the dtfferent dtasterenmertc cbntbrrnaubns and there wcutd be an eutttbrturn between thern It ts vErv th tcutt tb brethct e whtch Bf the annrmers at far Exemptet rnethvtcvctbbentane ts rnbst r9 We wttt shumv see that the eneretes ct the annrmers ct substttuted cvctuhexanesftt a reeutar and breutctabte pattern pmhlem Draw the dtfferent cbntbrrn ers bbsstbte rnethvtcvctbbentane SM PrEdtct mtch bnes wcutd be rnbst stabte br 54 chair CVCIohexane As we sa eartter Evctnhexane ts the teast stratned Bf ah the rtne stzes It has netther anete stratn nbr tbrstbnat stratn Thts ts because tt can Pucker tn such a wav that an ct the bands are b ecttv staQQEredt and tn thts annrmaunn ah the and anctes are meat Thts cbn e because tt tucks We a tbunee char In the chatr c1 c2 t are cnbtanar the c1422 and C3434 bands are barattet whtte c3 ts shave the btane and 5 ts betcw the btane br WEE verse t I n t ttt tu H e a i Mu m t n H H H u H x w H J39 t t m c Ther are twn CrH bands tn Evctnhexane The vemcat bands e kmds ct are catted axta The hbrtzbntat bands are catted equazonal and thev t Dr T e n u s x u a a W rbeens farm twn ctbse btanes MWHE the SM axtat hvdrbeens are shave and betcw these btanes Axta CrH bands are artt tb ether axtat bands and dauehe tn Equ tn a CrH bands and rmd bands h bands e 1 c3 and c5 awaT CrH bands are paraueT td dhe a e The ehaTr edhtdrrhatmh Ts SD WDDrtant that Everv haw tn draw Tt DTDDETW Start err thh bv dr wmu student must Tearh a a sha wa draw the same v but HDSMErdDWn ahd mset tn the Mt a httTe mt e 39 Du Theh ED tt th hds fthe per and T er Vs v avE vuur c r The D 39 m the man the paper tWD C39s DH the waer Huht are m from of the wane ct the paper and the WW C39s D the up zft b hmd th Ma et h er qu wedded ahd hashed hhes tn shdwthTs but must pedme ddht bands aTterhate up and ddwh amund the rmd n n u yr n The eduatdhaw CrH bands are drawn sdthat thev are paraHeT tn the C c bands tn Whmh thev are artT Draw the Equ tn a bands ct the WW DutErmDSt C39s rst The Equ tn a hdhd DH the Eftmnst atnm umrts tn the weft and the Equ tn a hdhd DH the erhtrhdst atdrh umrts tn the erht These bands shdmd be paraHeT tn dhe another and tn tWD rThd cec hands when vnu have drawn them the DutErmDSt Cs shuum Tank hke DrdmaW tetrahedraT C39s thh the twu CrH bands In the wane ct the paper and the twu rmd bands ddhd mtD and nut ct the wane ct the paper m m r a u M Q Qt T e e equetuhet CrH bands are a sD DaraH2 tn the bands as shuwn bv the arruws Agam the equetuhet bands DH the gems DH the Mt Dmnt tn the ME and the equetuhet bands DH the etums DH the heht untrttu the heht e H e e H 4quot Ir a H He gt a H 7 n tt w he av we draw the Evcmhexane T the curresuunds tn 5 he mu d2 Wm a sn Shaw h the 0an Wav tn Eam tn thew a chav StD Drac Ce If vnu Cann t drew a chew DrDDErW theh annDt ummuhmete DrDDErW and thts Wm ead tn reduced scares h Exams Cnmmnn errnrs tn draw a substttueht ncDrrEEtW bv makmg t hetther awa nDr equetuhet Make surE vnu Dmntme awa substttuerts DH thefuur c2ntra C s m the hght d rEEDDn H T rmng H Hlong The terms aan ata a and 615 trans desmbe unre ated Drnuemes substtmerts that are or are a Wavs DH the same equ ct subsumems m ths ththe ttrtd are cts ehd whteh are trans n n H n Ahv EVE DHEXEWE ttrtd eeh theateueettv Extst th the dt eteht ehett edhmtmeudhs The trtetedhvetstdh ct dhe wtth the dthet ts netted a ring flip The ipped chair is drawn sirhiiariv tn the first chair that we w eat that the upsidesdnwn v is ctrset tn the right rather than when a cycinhexahe rim flins frnm nhe chair tn the nther all axial xubxtitueutx become equatorial and all the equatorial D5 dre 2x tn the izft the xubxtituentx bemme axial but the 05705775 reiatiarishi subsutuents dnn t chariue CDnSidEr the structures heiaw The cath und ah the izft has Six deuterium atarhs that are an equatariai Each D is Dans tn the D an the heiuhharihu c This carirarrher cah hderua a ring ip tD 9W2 a new iasterearheric carTarrher in which H D are axia iri th riew carirarrher thauuh each D is still trans tD e D u a e th arithe heiuhharihu c The twin chair carirarrhatiaris ch a substituted Evciuhexane are sametirhes stereaisarheric THEV maV be cnhfnrma 39 hai structures We caii the stereaisarheric pair ahrarrhatiari rid rict cahricurauahav because the chair ip is a speciai kind ch retatiari abDut cec a hands hm WWW h I I hwmh M WW w wh er we drew the cunfurmatmns mt mtercunvertthmuu fhu he Wu cu rm 5 new 7 mmethvwe Exane at canfnrmam a m Dmers c usethew ht haw m ehsmhs e 9 Me e rt as are the r em ncaedff2r2 twu euhmhhatmhs ct c154 mmethvwevemhexehe But the the euhmhheuuhs ct crsr127dwm2mvkvduhexane are eurtmmeuuhew Enanhnmers and the t a euhmhheuuhs Bf DENS39LSV mmethvwevemhexehe are dentma Ve ir 3313 s VA Vie v Ne w w w we h Me mm Eve s Mi Mi prnhlem 5 Draw transr14sdwm2mvkvdnhexane h ts tWD thaw eehmrmeuehs and determme maher the W0 thaws are dentma nfDrmaDDna ehehmemers Dr canfnrm mna mastereemers Then an sem urthecswsnmer A manusubsututed Evdnhexane such as methvwevemhexehe hes tWD Dwsenergv mastereemehe eehmrmers ehe m Whmh th subsut Ent 5 she h Whmh m s r h we mterachnns accur bEEWEErv H amms Whmh are smaHer We hmeete DHW Lasmawa hteremehs bv ushe Darerftheses m shew Where me u 2r emu s bump he he sham x n u w Me H H M H H u u m Men hmhmwm WM m Tne urrrerenee m rree eneruv A6 between tne awa and euuatuna ebnrarmers er metnweveranexane rs 1 a kcanD Because We have twu Lauraxrar mteractmns between Me and H th makes my kealmal difference in new fnr eaeh ane We ve a readv seen 9 uene and nrarmers er butane rne numbers are tne same eea se the straw unurnatesrram srmuar sauree rne awa M reratransnrb wrtn c3 and c5 er tne nnu wnen rt rs m an arm r2 atmnsh ur r e Equ m a nu stern straw rs Ubserved pmhlem fnr hnmE a Ca cu ate the ram br awa tb equatbnar metnweveranexane tnat rs present at rabm temperature Remember 4mm nenee tne euumbnum canstant rs ca w ated bv K ruurn temperature 295 Tne rnvestruatrun er ma ecua eurrurmauuns and ner reratwe enerures rs eaueu nnfnrmalinnal analysis Drrrerent uruubs snuw e nnu na mure stene bu k tn sutuents er camparab e srze and tnese are m tum aruer man sun nvbnurzeu uruubs Emma atums have vErv ht e stene bu k Tne co H uruub rs smauertnan the pn uruub because tne cro bands are snurter n tne c 0t nere n u attaeneu tu tn sub 9 e tu rpr but tnat tnere rs men a bra Jump wrtn trBu In fact tne trBu uruub rs su arue tnat a Evdnhexane nnu Wm dB anvthmg m uruertu but t m an euuamna busrtrun x x u u x a mu ab x a mm W h Ne w m E mm vs 7 c a 393 mm o a n be r CH Wu Vuu can ca cu atetha Drnpnmnn er eaen munusubstrtuted Evcmhexane tnat Ewsts m the awa ur Equamna eurrurmatrun bv D uugmuthe eneruv er Mo Lardwawa mteractmns rntu mafurmu a K 2 W mere R rs e unwersa uas canstantU 937 anD K andT rs the temperature at mrch tne measurement rs bemg maue usuaHv ruum temperature 295 K The situation becomes more complicated when we consider disubstituted cyclohexanes We need to compare the sum of the energy of all of the interactions in one conformer with that for the other conformer For example let39s look at trans12 dimethylcyclohexane It can exist as a diequatorial conformer or a diaxial conformer The diequatorial conformer has one gauche interaction 09 kcalmol between the Me groups and no 13diaxial interactions other than HH The diaxial conformer has four MeH 13 diaxial interactions 4 x 09 36 kcalmol but no gauche interactions To see the gauche interactions look at a Newman projection down the C1C2 bond We conclude that the diaxial conformer is 27 kcalmol less stable than the diequatorial conformer Let s look at cisl2dimethylcyclohexane One conformer has two 13diaxial interactions and one gauche interaction between the two Me groups The other has the same We conclude that they are exactly equal in energy In fact these two conformers constitute one example of a pair of conformational enantiomers Let s look at cis13dimethylcyclohexane The diequatorial conformer has no gauche interactions and no 13diaxial interactions The diaxial conformer though has two Me H 13diaxial interactions and one Me Me 13diaxial interaction The Me Me diaxial interaction as you might imagine is much more severe than the Me H diaxial interaction The Me H diaxial interactions cost 09 kcalmol each but the Me Me diaxial interaction costs 37 kcalmol The difference in energy between the two conformers is then 2 x 09 37 55 kcalmol This is a very large difference in energy Problems for home 7 Calculate the proportion of cis13 dimethylcyclohexane that exists in the diaxial conformation 8 Compare the steric energies of the chair conformers of trans13 dimethylcyclohexane and determine which if either is stabler If a cyclohexane is substituted with more than one group the stablest conformer is usually the one in which the largest group as measured by the difference in steric strain in going from axial to equatorial is equatorial This is especially true for disubstituted cyclohexanes 55 Boat and Twistboat Cyclohexane There are other conformations of cyclohexane besides the chair conformations The boat conformation of cyclohexane is also free of angle strain In this conformation instead of C1 and C4 being above and below the plane formed by C2 C3 C5 and C6 both are above the plane The boat conformation of unsubstituted cyclohexane is abuut 7 u knanDt hteher tn energy than the ehatr canrarrnattan Thts a ts due tn tarstanat stratn rnnne the fnur c5 and c5 and atsa due ta a agpole trteraetmn v r aas straw betwee the H n c n c th patnttn s ane e rett v2 bv twtstt a ta tstsbuat ts antv 5 5 keatrnat hteher tn enerev canfurmaunn The tw than the ehatr stttt a eanstderahte amuunt er arteer but net as hteh as the heat H H H H quot tt tt n H n H u tt H rt tt u n n V new ydnnexcn tmt mm uhemue In raet the heat ts a transtttan state an the Wav rrarn the eha tWtstrbn t The twtstrbn t ts rarrns er the ehatr The energy kcanut represents the enerev barrter thraueh whteh Evctnhexane ust pass befnre tt can rttp rrarn ane ehatr canfurmaunn tn the ether 7 a mum I Remember thatthe twtstrbn t canfurmaunn ts hteher than the ehatr b 5 5 keatrnat antv rar unsubstttuted Evctuhexanet anuraprt ate subsutuents can ratse the warm Bf the ehatr retattve tuthetwtstsbuat unttt the twtstsbuat ts rnare stath than the ehatr 13 prnhlem fnr name 1n Haw manv mttereht mastereumehe heat euhmhhers at methvweyemhexehe areth2r27 55 Faxed and Bridged mugs e ave eheedv seen the mtterehee between as and zransazr mmethvwevemhexehe suppnse 2 mm the the Me emups meet 2r h ndfmmtansrlesd m h mm d c h h farms eeehh are asteranmers ust We as and 7 57127 mmet chdnhexane are kae s dwerert Energwes becau e the w substwtue ts m DHE chawchaw h much are equach M the ether w rs Unhke vans 12 m vc uhexanE a rd W he c h DH D2 255W make a W de at 057757127dwm2thvkvduh2xane and se aw th d haw 5 CH2 e u ts nSummEntW mm m bndge them na erecahn S sen tn be conformationsy 51371 stjme wl clalxexane rissdecnlm Dj f gt Ljij 7 w 7 J I NI p mm 4 1 immywcyclnhnm mwdmhu Stermds canswst m severa swxrmembered was fused tneemer These 5 net and perspecuve m H W e H 1th We can a sn have Duwcvchc cumuuunds that are bndged In these cumununds a chem m me ur mare amms cannectstwn nuncunmguuus rm amms The e cumuuunds can be bmvchc m mcvch Exammes m campuundsthat have bum bndged nngs are dextmmethnmhan fuund bhet as a CD uh e n h nhe wwth a N mstead cf C Twn cf these are crsrfused WE are transr fused and WE are bndged There s a sn a benzene mg fused tn nhe cf the Evdnhex she was CY xmmw mm Wm H WNW m mummy


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