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Comparative notes from Ch 17 & 18 from Dr Rogers

by: Carlos David Fuentes

Comparative notes from Ch 17 & 18 from Dr Rogers CHEM 2322

Marketplace > University of Texas at Arlington > Chemistry > CHEM 2322 > Comparative notes from Ch 17 18 from Dr Rogers
Carlos David Fuentes

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Here you will see detailed information about chapters 17 & 18 about what we have seen in Dr. Rogers's class a year ago. Ch 19 coming soon.
Organic Chemistry 202
Frank Foss
Organic Chemistry II diene dienophile huckel rule benzene derivative foss phenyl
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This 25 page Bundle was uploaded by Carlos David Fuentes on Wednesday February 24, 2016. The Bundle belongs to CHEM 2322 at University of Texas at Arlington taught by Frank Foss in Winter 2016. Since its upload, it has received 52 views. For similar materials see Organic Chemistry 202 in Chemistry at University of Texas at Arlington.


Reviews for Comparative notes from Ch 17 & 18 from Dr Rogers


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Date Created: 02/24/16
)1,8, 1l9 t-.n+^ o^vl'-lua*odi.rrr,Lde,2/13k015 Chapter17. ConiugatedPiSystems and Pericyclic Reactions Ifreclassedienes,' opl "*,!["=#:,. @r [, t c%ra-ta dasbbbad ) fsq/qfdo,,!tb** \- tpz'---'-/ & 'tl*rJnd dr&+ rse,b&/fd o.n,xn?o!{*,}*ld c"lwd r bqq fuid< 2n l.ank by-*eanl,nlysrrgl6erd TheeffectsconiugaduetoO*rJqpp?t p-r.6f+4g /\/ m l,'!^pnqla&en, ),t-b,iladruqe _V B-*ufiu.edttte{*nu b,r*a-J.3pene, ?Bofqu b, buWZ-o,to toltu6ctk/ fu+^eo-z-one &riluao+,/ Sea^aploltUqdyqo 1++r-Eclasrlqkl*a, J,b qcbhuolrrns teo/afzJ Preparatoconjugated dienes: Conjugadienes can berfroallylic halides via an elimination Br klce- f-BUOK iil,o:*'r 4\/ i(l Potassium ferf-used because $lrsq sto.ucoll/"d*d&.st 82u q rlffi MRy bgo EZ occ,rcrvJlr.MorEu2 17-2 These reaction cocan albewrittas: kr Ocdcn l. , 6-8r0- or &,ua).coru 6-&rets Bondlengthlnconjugatdienes: C+ J${p,a J40Bn )*!W, C, r C=c j33 p,,, I 4/\ G0 JZT Bn C, Cts {fu AttC or.spz Cz-Ca Lond fs wd *Laqe.'{s, ilv'+* +hr,rspbolqne fmoh*ta."&f{ull Q: Whyisthe singleshortithe conjugated BrSlenplnnq{p,? [4A ;p*rt UB +heory re A: The C2-C3 bond in 1,3-iformeUytne 0l#r[Xp oZ hybrorbikls. -SPZ Sin"* 8/e orbithave \@.fO s charactnan $P3 o*italthelectron density olsw to the nucin an ---8+- orbital, so t," bVhortf I Zs spu 8P sps 2 p o*$r}oi 0!, %7o BiYp WPo wyo S Chu'a6fu-, s /*,a6{er 3 c{qnocler e, S d1onqc+17 17-3 Sfabifiof conjugated dienes Review Alkene Section 6.6, Stability: hrsak{r+.,led +cr.t"*r+*+o drs,hh{,{td lrnr-rrlr{rt+rd Recall that ofhydrogenatareanindicatiof the stability of a double bond: 11, .^'-r' AHfi,o* .-Jz6 nt,..a PJ ^dt lr, ,'^r/ Afufu*rrrolson.^J I("'-Y^a 9a /t ..\Z tU" ,0,/ k0 fsq ula*r,!' ;6,t &qtusr*1,o, 4{* tL|Voa /\,/ ll Q<"dpn Coo^d,inds lmpofiantrne L@r+€r the heat of hydrogenationthe rnore sthedoublbond. Compare the following heats of hydrogenation: Compound K:V"a -J-zr, ,.ronp-subs,tot"U M -lrb L9^a dr*p.1. *,,leJ V 17-4 m_2S3 KL A6-rdufL*{weutul<xpet ./4ol ? *z3Zrct/n,t "FzQl> M -zzbtv^.r iffll.ff-iu kv,,,t Calculate the enerof,3-pentadiene: Qi1r[*zzl= --J6kV,l Why aeonjugated dstiathanisoldienThis iexplaiusiM0 lh*.V Becauofthis rncstabiconjugadoubl*boarthereferred of elimination. *ffi O+ lry) - Twoimportconfotmatit,tbutadiene -Wilff',*,i:;;:f:,;*,o, rulqlBon6oqlUC aen6ly$snd((", ln,s-hk;' ctvlpkei' tfr -SI -A- / uJn) &eg .t'-rs CB S-hoqs ^ ln both of these allcarbon atoms Dreh4fieteaeptane,oUoutofip-,.ibflots roour"/qP / N 17-5 Electrophitic ofonjugatDlenes Recathe electrophilic adof alkenes: & Mq'tau*hau t+h A-r + Enqq{wn* R'sw'ot'rn+, M l+n" Qoon V.-^_ Qqw,chur$n1w Arei 04, IA, CHe /\nl*s4reocj,utslqr aP$13 * Fuwrfn^e, aB, Recall m*hanism electropaddition: @ P^ofol,qns{Q" @U*trfiilroql+",c.t ConsidthedditiofBrand Br2to 1,3-butadiene: b. HBT (cH3cH2)2o )-z*usb, qi*l,e", ^-/ s.^. J,e- J4'aldrho,trdret pnoduc* Jz- udd*er Jtl-uddotl' Recstability order of carbocations: LaTlro Predtheroduofthfollowing reactions: UC- *h *Qnan4-swra, r# 6r1['-*Y'"ll#J Awt'toned uddfu +rb 6 $-.a 1 L'@: 6*1+ff*.1n +^*?r^r, i, qh 17-7 0A y-llal*f,Al -*-n,\ KinetiControls, ThermodynamControl Compare theofsroducts: HBr Y' 'ga-'&lod Ll-atd"et r'\r' ;lh"- --\^ ,,AAS, atoocYJ l,Na/ro, 2gy" at40oCJb'/, B6v, l4oy, Why the differat differentaturQonsider mechanism: p>urfill#]\ ,y_.+Ms, Draw tReaction Energy Diagram for this reaction.Te"fLrreoys 16o L&*< A{# d1a t,W"p*W^th Yno e{-krt Lnrou 4t-Z G S. g z-dd*eftlo*kblrl L. R?n{p W"e{ 3^E J.{-qodoclntoeh]k/ *h*n le,rw,p^qJrcF crrnftnqls Ro*frrc, 17-8 The 1,2adduct iscalledthe ktnef P P.qdrrclt because thereisalower leadingtoit.At lowtemperaturestheprocessis $rncW/66/O .A reaction isaid to be under krn*l,, COr$nJ when the productdistributiisdeterminedby the nelol.rua mlp s atwhich theproductsare formed. [thm Upo-fl,'rffu "pk&rJ The 1,4adduct is called the Arlol$(i because it the m.or.l, al.d[t0 Pnpdiftl ..At higher temperaturethe reactiis tewnlbb ,allowing the less stableuctto re-form the allylic carbocation. A rissaidn to oeunoer fio4npJi1"uetn/O eAha/ when theproductdistributiis determinedby thestability of theducts. The Diels-Alder Cycloaddition Reactr'on Be surethatyou know these named reactions: Diels-Alder: .'-..--.aW + ( I ( \/ .lproceeds Yiaa U4@r{4d process,whichmeans that allhanges in bondingo""r, €P,4 UI -ll .Thisisa good rnethod for forming .The Diels-Alder reaction is called 1. Thinkof the mechanism this way: W _> dpqt dp{o$./ *k, 17-9 2.The Diene beable to'aqopt wnla,.nq[Pa,t p,) $-cPS n [ry- Thereficould not be a molas:le such @ B+une (n^J-q{-lretdrerc 3.TheDienophilekbest when it has @rtLsr croruglefroo-ullfid,.groq,S sucas: Oa n 8tn frt frt N ffr 6"- rf"'o tf'on (ct' d-oo CYano The Dienophile can also be Wt alhy*,ulln, ?Ectrs a: r,r,rdfutE,,^1,,s A Utbslr{"al ul cI @rcQ 4.The Diels-Atderi"*{en€oSpeOf-fg 6-q"o\coon er--?* !i' \-h Cpott Whena bicystructiformetneA{LIO produisrefened. .^ Wbtynb *allto e$ targob*ObO QL rg; 4gah,y,6'dss \q h 17-10 6.Predtheroducts: r'\r' + o fr qA -+ ffio-cls o \Q"'gt& kow^to otf z\r' + /"xlr"\-- feuarn'ro'*[p^Ua\ o+ o 64 0 CN + -./ a.aut7[Bpapq Z\r' * -4o OH o. 6.^--t\r,r.t 'sgr,-;ut -) \j 17-11 BriefReview ofMolecularOrbitalTheory 1. Summaryof MolecOrbitalO)Theory: . €xi1yZ6r2p,\3elo Quantum Mechansays: Electroi" qfur\q exisin allowed estates called Electroin nJgcdS{ existalowedenergstatcaled t W O,ltlrlN&) qn+"$d*oa ' Think Mosthiway:they are fofroma w,,Ag"qlAq o^ oL A0. Forexampltwo1sAOs will comtoform 2 MOs: @jcg.* -1s O c (-2e1. - \J n Twoparal2p orbitalcombintoform d MOs: P ,IC\ p &[ I+ aa O fcLp 2. Two equivalentwill inttofortwo MOs: - 6OnrhnS Mo, which lOu{r " i" in energythaAoshe -an MO,whichi" hBhg. in energy thAOs, and which }: always has a between the two atoms. Bonding MOs adesignated €[ anC ffi tvtOs. \-/ AntibondiMosaredesignated O-k ano Of6* uOs (pronounc"sigma "pi stafand stamolecutorbitals). 17-12 4. DeterminMO electron configuratito determining AO electron configuration: "Arlk t p.o&durL E*cl.,e*t, '&olf Prgncfp,o '$"ndk "ulr, ConjugateD ieesandUltravioSpecfrocopy i:**^',1 Izffivy 1. Combination of two 2p atoortwnrmolecuorbitals: f'*rfuer-S6rlsls .,- hql (]nocru6p/ Ju{r-budfS^ i ,.-&[ YLx - T^ ^'tLUMOti*;ihj" ?nk,adh4 - I 'n ul Ft,,:.., lau, 'rggqo_Lu}40W /, I V 1!-I HryuasOccupped J"bondBnd ie{ " fulearO^Ar{ql [4kr,i.#, l+CInt0 2. Combination 2patomorbitals: Z we .iit:#,'fiylri'*_ffi %)r* JI q^*1}W:.khffi,tr- f,*-pu,.,ro lou Y lwo LUt1oc4k1 ry,r,{ aono #,*,t{.; trffilfr*k "ffivr* 5 6o"d^r,,'Jelu"ks4s 17-13 3. Combination of six 2p atomic orbitals: -^\Z\? 1$L Ul@ d_ r0 0\6iil ,LLuyt| ffi AY HAUA^tW,ta T ailq A\1!.t'tot'11*. ffi TzY- ffi ffi\rY 4. What happens to the HOMO-Las conjugaincreases? lJo,t/0-Lu} dwwses u^ilfrc,.eq6u4$ wfugu4$d,l '\ 5. What type of electromagnetic \." thLUMot ?,re ean$u6n+diatioP hamount energy reqtoredmotan electronthe HOMto ryd*oO UV A*/,nq{e) 6. What doatypicalspectrum look like? A^w *he *6s''6qaco/ h gAf { 7. Remember: The hthe wavelenthe, the eneofthe HOMO-LUMO sap,ndtne the desofconjusation. lrUn""l{^rn ,lAr^rrn Srua{lf TAO u ea$oVekl Examples: {\A ethylene C=c. ) :-16q,,) l+' 'H ^* 1,$butadien A*NxrZlYnn ^./ 17-14 1,3,Shexaki 45\-/\U47 A*w=288n^ 1,3,5,7-octatetffiene '4^*.= LgUrn 1 .?. F-carotene A,q55n, [UrsreU ltsh*;\W-Ysoqrl WBG YOR 8. The"eolwheel" 9. \A/hcolor of lighB-carotenqorb? Bl,ro WhatcolorB-carotene? Orjrlgg mv? Becor^gr wo pertetuoht **plueql .J & blru_ SnQ,ngo 1&1 Chapter 18. AromaticCompounds '\---OverviofChapte18and 19: Chapt18:Aromatic Compounds: 1..[,i\o""r*r,Lo.W,nc,e[w pq"*] beq>u+ z.&hbrh{1 st sA^o,aql.rcl{i il'r'e,fuo's\n*Z fGd a 3pc.t*scopvJfl,lifui4A.t\C NMR, Ult/tlt, Chapt19Aromatic Substitution Reactions 1.Learalltheeactiandbeable to usinsynthesisblems r^ \) -L=6; cit #o o #$,q- ry* Wry,U, llzS0,t \, [otrry^ F*<Js.! CroslY ttr b#o^^ NoteThiisnoa complelisTbere othereactiinChaptelthatoumusebamas well. 2.Learn all of the mechanisms 3.lordeto conectlsynthesisblemyomust understand asubstituent effects. Thameansouneeto know T19.1,ge899. 1&.2 Nomenclature *aromatic" - bn*x VtrfuUt^l\d eapoondg '*w;";:;t*,,u TI IO'*OJ u'c-qyI''r l+ Allothe carbon atoms iareegpZnhryb*lfrel andarr atomslf Y-nVlt ryrrqgpfie, Recathesbondlengths:c_c IS4,o/0, c=c,l}3prD c=c .l?9 pnt ln benzeallC-bondareJ69 pfn MonosubstituDefivatiofBenzene: ry*o' o Wg:,, qglrok/1xo?' ell,l6uzene. 8e surtknow aofthescommon nameswhicare accepbylllpAC: ry"*' ryo* 0o-"" ry*" teiuaa Phensl 0rrfsola Qnqlhe 18-3 6)-"-"r'' ry"*o er= 6er*w bu.,ldil*1do Qcdopheno,te GlY'u'" aryd Arene- ltharksroupas<6 carbon athe compound i* namedl.*bgll,Wd bWzeq(, b*\tbuune, (l- u,tyb*r,rs "dh4 lthe alkylhas>6 caratoms,hcompound is named as ) O *pherylaclrqa 16-/rphenylac4a,no phenytsroufrlJa Benzylgr.6&-eHrl Benzylic carbon I I Or?" tr er' ph4 DisubstitBenzenes: o^^ cH" CI Noz t" A-o ,\ lt-l \rl-*o, a v Br g. .0- drhbroluuzena @-dr^il,obea7(, .pg-b,o,nr4olutne O-dpohloo bw.ens g-dPnlh "beaz,no r- b'enofoj*ere 184 Threormoresubstituents: CH" orru..*,9\)No, 2rel,8{nrex+,hluw s\/s Noz T/\lr CI 1\J cr cl-c-c-H 1,1,1-trichloro-2,2-bis-(pchlorophenyl)ethane (DDT) u'//\ \*/ .cl A mosquito was heard to complain Thecause of his sonow wasain. p a^q+chtu o -!rphnyl[*chha e[lwqo Evidencof the StaofBenzene 1. Benzennr"contsuol,lluunhq{ oAh/drogenqAfon Affo*vt M, rf) , AHJrr= -J1o W'qt \-/ Qa/C.Jq+,r o l+, ^252 kVna o Aftl;,," A/c, _lq,o ln the abofconjugatwe would expect -zq\ l6/",t so1,cyclohexadiene hass 9nol stabilizenergy. n'^\ P'.J0o't' uV^a * JS0'c AHir,'-zoS W (;f kWi With three isolatbonds,would"rrrrrb X ZAl,-b60 so benzn", trCD-ZAb, )82 Wmol srablization enersy. 2- Unlike alkenes, whielectrophitaddp{fOO reactions, benzene is unreaetectrophiricfo, 18-5 But l,r> H, - \r' Pdrt,iat*r,)"I { e,) OB,.- Gil Buutrf\ bn - D-' lrb,vqc(roa f*u'' o u" But lB. f)sreal[Wo 3. Unlalkenes, benzene undergoesg'ld'Porr reactions: ww \-/ r\ 0JU0 tzffi.;* ur% The special ofbenzene, alonabitounoergo/€04@/6f/,PO ,".q[ru At SuLslvluira.r is refeasd to Atot ryl'l"g\ AromaticanH0ckelRule Three Requirements for Aromaticity: t,/h "l ZpL 1: *)nl *P'YL 1 1 A planarnPrtg 2. u$rrsa,v h,1b*dt.ed e,*nS/rur"lqppfie kil-/onflog&-frll apz Ltnbt pn.6drle' .0b.y's /du"t<"l(lo, 4,t2 fce- sowhydoesHuckel'sruToanswerthis,wemusMole,rlor6sl0,T6eOg Athisointneed to know that tkinof molecular orbitats: 1 pendrnq M0! r hqu, ,,nqr.jro&ogr,)t?^"6{qW aqhbwd*^3 ralre.$tu"g , (nl^rboqJro$ L*dW+'tle clPo+s M0* I mart-Ot"a W Hiickel's rule:r^dhsMOu # An{tn[^o"n*.^r1,ry=:@ u]*n"*wa number nelectrons 0i6 Snfarte t5lo l,/ Consithemolecorbitals by the intofhesiorbitals on benzene. NotThiMO can be depicted as -vv( 0bonfua l6 b w"{rLodtrr3 -- 5,,\l+b@adf1y, ,7ffi 0 bonnltng Lrndus r rjt Z^{r$orL#alaniPbr,pthg Y,, w 2cntfi6a.dhg :;ry z*nkbondtO '(. l4 Is,r{0,rng uarlr6e"-41'ls 2 -2-bodln5 Y,lt' ?fie bo^ofini \t0 6 fnte*clpeas ]&rL_ dfaarnirrnlv"ur+p"^. bo^oU1g . Or: 6 ^,L '-FL s %L t'rnu WL \ n,:o 1&7 Summaryofthe Molecular Ordescriptofbenzene: '6atomicorbitacombineform G Mobcuraorbitals3 bondiMos and 3 antibonding Mos. sinceachMo cacontain 2 ' ebctronthe 3 bondMoscan contaitotof 0 n electrons. 'By occupythe bondiMos,asix electachievatoweenergy stateare sa,o" dOl\Urlk d Thiithe sourofbenzene,s tlfub|ilfrqkfonlaby qal ,tthataboutT,scyctobutaarenee 4Tto y ,Qn /i,UcA'trlopdnft q*^qlQo + hntrn*rrqkv [r1_ l*i-l Ytr q orr{'r6odq$ ( IF--l ffr"r- N^ , 0 botdPrs q WL 6o4dh5 tqk,volsra Or: YL Anhb*o,tr'u 4CI Mo,#"ansMo Y"s:- {\Y -WtL \rJr,a Nl7 As a res1,3cyctobutadisneO^{fn**ql.fa, whichmeansiisarticdva WJAblL AntiaromatQlqndc Cr,otruukd nr,g syb+ra **\ \ rt,16 o Why doesHiickelrule work?Thais, whmust aromaticcompounhave4n+2*electrons? "2" becaineachMo diagrof_ glClfU ooqddgeiAnl structures, , , the lowest enerMO alwaytrasO nodeanditcan oncontai2 ebctrons. 1&8 .4because tenergy orbi*adWnapgk,. pqfn ,his 2 orbitals of Assumthfollowing areuctwouldexpect tbaromatic? 9(EP" @/sp' A -. - Cydopukdrenyl_/ U \rce; ,th*or.r&g U4J@n C,0q+Poo,nlqdNono*^rl0 onlPo"o^qffoot"teonSWk6ro€ 4ns- LlNr1wnryaled *rw,,vbo J/n+ra"errqdVo aavpB o za-. L81An^ulep lt \ A Skrroqlrs,to L/ L/ 4ntreo*rnql-lo Fpguaplr*nfb Ap@Urdmq.}.$o Nr^nbc, [oasr.plq*o.J @fic bns Ert Noraro,nd.rc IJ{Annulns J0rst A,r^qko A,bl"oonq-ilr{Phn* icfl H rBP, t ,I=A n'* -zllr as-. \_/ TY, L/ Q HA-L"n* 0u.nolo Fu'wrs J[rophen9u'idrnu Guqn?na NI A^o^ofru 1&9 IRSpecfroscopof Aromatic Compounds sp'c-Hstretone or more signalsabove BO@ 0 cq"l -17ffi1*2000 combination baand overtonea;roupof very weak signats ""{ -l {a0 --loo[r C=C stretchand ring vibrations;ge3signata 1tlfr 1600, J6ffi GIS-0I0 bending; specfrequencies can inmonosubs, a, m, odisubs. lR Spectrum of ethylbenzene: t00 tu u I 860 \J I Jtoar' LJ4so H NMR r ,[is Recall thchemicashifts: vinylicoton {J_6S S ,k, . t+ g aromaticroton g) 6S -8.0 deohsrued Whyisthe aromaticotof1qlhdqwnfield fvinylicoton? Pe* Ctlrrenl theroton. rrt s 2,+ >>B S \ ,t B" f^ H H+ i t t N- , - 1*' 1&10 The splittinis usuafly too compunlesisataPucq-dmrhkfufrd c.ompound. An unsymmetricaldisubscompound: x Z kUdsorp^olo,q ?t+ tl.y u$ ofher ztl \.9'uo splrl u.A4ul o'oLdrdfds ,llll, BO 6dS 'HNMR spectrum ofol: . 9n>E"ZPPq r+r cl.le no.0g.q t zJo,AlA drs,6s+cluld 2alS Uneu{u*{ra rT t, I I 'l'l ' I- -T--- 11 10 I a1 ; ,!; J 3? 10 HSP-03-Et6 pprn Aromaticcarbonsapp-lCIOJSO ppt The numof signals inthat area indetermithe substitution 'i& Byrn-par^d65 ,#:: t & b ryffi* *;.;-Ja* { 2-oPsnds X i( /.v'x Lrl., . o"'11,0 #" aY dF.r6rfi{,f-d 6 s13na( Po.q .l^eUn"rr+rtq, 4 strq G'ttnols "c NMR spectrumoxylene: cu 7 b eSral5 -clt3 n) zoo140 150140 12100 tGoEE Fprn NMR spectrum of rrrxy,lene: "c clJ.. ltts'"& eA-1" / dt(A"r -cHt- ,) 2001a0 160 ,.120100 a0 60 40 zo o @Ge Fpfn ''CNMR spectrofp-xylene: cH! lo uz\,s ,V CfJB (--l


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