spring01-final-soln

spring01-final-soln - I":i"lemistry 3A Spring...

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Unformatted text preview: I:.":i"lemistry 3A - Spring Eli-I11 Final Exam Prefesser Jean Freehet Yuur full signature__ _ May 14. 2W1 Print ye ur full name__ _ [Last name. First name. Middle] ‘reur SID __._______ Please sheet: the seetien number and name efyeer GELI'TA. __1E1 Padilla-Elle JESUS-,Ci'rnayra _3?‘l Miljanisflgnjen _i?i Fez-{Daniel _3':I'i Siysmaniflsje __1E‘l Furuta.Paui _32'l Ll, Ben _‘ifl‘i Ling.Fraril-: _4E‘i Huangfilan __‘l11 Cerdare.Jeae-ph - _-i?1 LiangLat'nerine _12'E Le.5t:hei1erazal:le _41”l Phillipsfieett __131 Thaijifieema __421 SaxenEiiana _14‘l Catherine Seeley _43'| Daterheutflebih _261 PETEFltE.DarGy' __5F3‘l MereileMaure _2?1 Miljanieflgnjen _511 Klepp,Jehn __,211 DerizEmiiy $521 Wufiarah _221 Simenlllatthew _531 Ftaefililtas __36'i EiarryDayid if yeu are msltin g up an l-grede. indicate the semester m, Hut Write in mg a“ yeu teelt 3A and the Prefesser -- ‘1._ {13} This exam has 15 pages; make sure that yeu hays E._ _|[1EIJ fl‘IEm all. 31- J19} . . 4._ _{EEIi We will enliy gra tie answers that are In the designated spaces- Please de yeur ssrateh merit en 5 Jam the baeits efthe exam pages. U'l'rite eniy m answer te '5 J31] eaeh prehlem; multiple arLsWers will receive gg credit, ? J13) step ii ene at them is eerreet. 3__ —f15} _ I _ El. [13]: Meta: The examination ru ns fer a teta] at 131] minutes. 10 H a} He guestiens will be answered by preeters alter the " - exam begins. F'iease write tegihly; smhigu ens er 11-_ JIMJ messy answers will reeeiye ge eretltt. 1E. _ - —_i'13}| _. 13__ _{1?} Tatal __;23|Ii} El 2001 J-l'-'l..l. Fretthefi, Eterlteley. CH. 31 [ Ell=tl3 * 3142- 1.12.2 '3' FUD: J.F-'|.J. FIE-Chet. Berta-Ella}. CF. Chem. 3A Meg-.1 21301. Finet Exerninetiett Page 2 ef 15 Note: There are he duestiens te he answered en this page. Nete that seme ef the date provided may net he needed ImlceliH MMR chemical shifts E Tyglcel flmfl chemical shifts fi Infrared stretching in cm1 I R_|:H3 9.111 '3 R_I:H3 5_25 Ell-H {elenhclj BEUUPEEED H_EH2_R- 124E ECHER. 2535 [2—H {elkene} E-Befl—EEIEID HafiH 1.4-1.3 RSEH 35—55 C‘Hia'i‘EW} “mam” e-cHE-c—s' 3.34.0 etc 30-45 E'Hia'mei 3250433“ R‘GHEEE 14$} ECHEDHR, 5043': I t..=I:r (aldehyde. ketenej 1699-151] HECHCI 3.9-4.4 H—CHECI 255:} i Sic imam] mafia] RD—GHECI 5.2-5.5 s—cccH firs-13:1 3:: talking} “WEE” FtFt*c=cH2 ate-en s—csch—s' ten-151:1 H—G-Dfi'tested 1T35—1‘r‘50 ecschs' 52—5.? FtEccht'E fine-15:1 E, ec sci-1 1.13.1 He see ee-es EHJ—E—Ft eta-2.4 cH3—E—s nut—22:1 e D ie the symbol used It: denote deuterium the ieetepe 2H at hydmgen Partial erie the table cf the elements. 1A 1 H Lends-t. 3I Lt £311 11 11 Ne M 1191'“ 24.3D5fi 2 He JIM W A VA 5 E t s - e E C N D F 111311 12.1111 14.111151 ass-tat 15.5934 1mm 13 1.:_ 15 1e 1? AI St P S C] 25.3515 25-1.1555 anem 31m 35.:511 4 Be 3.51121: 1'3 all a: 32 as :1: :35 31:53]. 55.35 5:132! T151 RENE lee FEED-l 3:! 33 :IE es $3 .511. e. e. .11. fi% E 55 T5] an 31 e1 tte_ en: as as Be At: HQ Tl Pt: Ell Fe A1: Rn 155415? 11:11.55 Ell-til! 1117.: Intent 42119} 4211:; 42:21 13132? LH Lt;- iii-26H J.M.J. Hutch-eh Emil-guy. Lip. Chem. 315'. May EUD’I. Final Examinaticn Page 3 cf 15 1. f 13 F‘cintc]: Fcr multiple chcice questicns circle t|_1e letter cf the best answer I'i-Ih'i. .1 - ._.- - :w The specific rctaticn cf pure {Hi-E—hrcmuprcpat're is éfliwhat is the cpfical rctaticn cfa sample cf {E}2—hrcrnpprcpane with an cipticai purityI cf 503:; "W .-' "_- l' r-'- {a} zerc {h} +15 {cl} 45 j:[’%+1fl {ii—Tl} [g}+'i"-5 {hi-T5 [i]ncnecfthese fll-I—ru—i—_,___ Which cf the fellcwing i5 pmduceci Iwhen '1 equivalent cf HElr is added 1:: “Imagine in. the presence. clearer-tides?— {a} 2-hrcmcvtuhexene {ti} [El-i-crcrnc—‘i—hexene [c] [El-“I-hrcmc-t-hesene {miniature at {c} and {cJ [e] {El-E—hrcmc-E-heitene [I'ji [El-Euhrcmc-E-heitene ._.-"' ' tg}mi;=:ture cf{e}acdl[f} {h} acne cf these .x-K , c- ._ :ar " " An increase in Iiitrhich cf the fcilcwing results in a climate—Era En theiatecja c lemicai reactign? [a] Temperature [hi Ecncenhaticn [c] pH [cl]. cellisicnfrequeney .-'"‘~Iq.. '- 5; [gt-activation energy].-I {f} time at reacticin [g] ncne cfthese .5 at. . .r-..-; .-_.-- _--- Which ct'the fellcwing statements is ccrrectfcir prcpene EHECHCHE I-r' " ' '.' ' "- .-.—T~t., - I“ ._ _ _ f- .. :1 _. tale“ nine atcmc are tn the same plane I; thyme mclecule hescieht sigma ccnde a“ H. -- HicLE'rcpene has has iscmers {E and E} 1d] prcpene generally.I acts as a Lewis acid r': - -- ' tees" IE stems in prcpEme are ac2 hybridized ncne cfthasa What is the fennel charge an each alcm indicated by an errcw a... i H = f HwD—N—H: “’ " 5': ' a a E ch many distinct internal _alkynesgdist with the mclecular Ecrmule tZfiHflI . " IEIIEIHIJ'I J.M...-'. Frechat B|-_-1-h:|:'|.'I EA, Chem. 32% May EG'D'I. Final Examination Page 4 M15 2. { 19 PeinteJ. {e} Aeeume that the energy difference between gauche and anti eenferrtletiene er tJutene eerreepende to en equtlihrium tnztrieterlti-t1an ef eheutEfl- Shaw 3 Hewrnan prejeetien fer gauche butane and calculate the pereentege rJf anti eenfe rmer at equilibrium_ Write an equetien fer Km and shew deteiile Elf yeur werk- '3- .- _ ._ .-" t I:- I'.| “.t-E. anti :nni‘hrmer = Iii-:- Newman ijecfiun {gauche} .-"' _— _ < II .I'r '-I II I_,.- If. I. I. III;— ._—t - I:- u r _:.|_ -" .' _-. e; " '- a -_._x “e .r — a. _,_,_ . H2 l.-' ' .rT' IITIEII ll.‘ _ I I I " I ‘ H " ’11. Li .'I {1| I r“ -~— *7» e I .. .| El :— ‘a _ .— — -- ' {I III“:— LEIJ h .-' '_ ' -' - - — .- xi—— - — . EH It! {If .-' J'lr Ir' I —- i “a. f5 r —_-'=" 'I --—I\_'-' _ LI' at 2am JJ'..1.J. Framer. l-l-erlmlay. CA ChEH‘I. 3A i'IIILZ-tii-ir Eflfl‘i , Final Examination Page 5 nf15 3. f 19 Paints}- {a} Name {If draw The italic-wing mniacules as appmpn‘ate {sham atarenchemistry} HEEE—EH'EGHEDH [bi Write a mechanism for the fulluwing reaming“ ,_ {3, CI (Flint: the bland CI—CCIE erg-l _ Sch: . a :- l. is Easily brake-in} [ (lit a F "~ i _3 — f '_3' d F 5" * liq r~_ a—I . .‘7‘? | 1.‘ r“r’ ' ‘1' 'l? “P I“ III -1 I “Hi I .x.’ ""5? " [F " r 1: “I " .r' _L . Iii-.1 . ' _- T if I" fix}: _ __. .__ -I .--"--. - If __ {/f __ . , .: 'm- t aw I.I'I., -33"- 3". LI}- _ i; i I! t? - i ll I I' a. . l 3"": Err-_- _.?" I “I I K"!- IW-1| L-;— v'. r " FA; II‘ III-h“ I-I' xn' .- - .' .- .- __'w- -: _.-' _1 I I I'IH _- -_ IL» I- n:- ~. . r ._. I . __——-} Er_z—'n- .r ' ' "i i t- .- -- x x L“3" -' . I' ‘ --t -1-.'-. Cfi'r'.‘ Fl . — I_._-.. " .-" i" "h—H I _' . LI,- . IIII _ _fi I.‘ F:_ fig; "1. P Cu; li- EE'IZI'I J.M..I.Fre:he1.Flel-keIa-,-.Cn Chen-l. 3:1. I May Efllll'l. Final Examinetian Page E: el15 4. [ 2E1 Palate]. [all Guneiderfhe nlerEhraminatiaflal'{El-E—hmmapenlane using Br; and light. Hew many preciu eta are ebtaineei by reaetien at 13-2, (3—3 and (3-4. write in: Llr answer in the he}: and allow a Fiah er praiectinn far each specifying whether ee eh ie ahirai er aehiral and. in ea see. where mefllhgflgggggggg ie ehflined, whether they 1llrlil be [armed in equal er unequal arneunte. _ Ha. :'I .. m Br -.' -—l — Reaetien at 5-2 5 er: s? H .l_ HTH ' , ell3 wn'ie "chlral' ar 'aahfrel' neat la each pma‘ual lul- CHE .-'~- _ — .—|' H Elr' - - ' Reactinn at 6—3 I u __ _ _ .- H I -—- — *- H H _ _ -——'_ ' H CH3 wn'rl‘e "chiral" er "a chiral!" next to each pma'uet r“ =.' Number ef preduete'. preduela farmed in equal E Drunequall lawmm;s 'r. “i. la- - EH3 H i Br _ __ .. __.# ,. Reactian at {3—4 H -H I ___ _i_._... ._ I 1 H . r1- _- _ _ ' _ ,.--"' I EH3 ', i write "chiral' ar 'aahlrai" 5- ' need it: eeleh product ,3 c 3"}. .-" I_.-' er unequal .juu- 'hmeunta | Number ef predueta: .ei— ‘ praduele formed in equal All e EDI'JI J.r.1..r. FremgL. Hru'ka'gy. en Chem. 3131 May 2001, Finer Exeminetien Page F of 15 Write NR if thrae is nexreeeliqn- x /A'_ f I a“ CHg—EEGE+ eHESH'i’,-'—I~ _.-" '-\_.- '\:=i 1} EH3 —-—1- 2] ngl2 I DH' £--.. . .1 .- _._ NeGH e' SH—-—:— 5- { 2|] Peints]. Gemplete the feiiewing reeetiene ehewing me etmeturefij ef the mafer pmduefiej. {'1 equine]- $20!.” .1 M .l FrE-ehet.F!EaI1:-_1I::.r.l'.n!. Chem. 3A Page 3 et 15 May 2061, Final Examinetien r3- [ 21 Saints). Cemplete the fellewirrg reeetiene showing the starting matuarials er reagents as apprepnete- Some reertiene may reeujre mere then une step. ell etepetreagente must he shewn. \ + enentiemer H ""‘CH5 CH3 H CHg—CEE—CHg 1} HQIPdJEaC-Ggfquinefine 2; e3 “ta/Leg EjEHESCHg Br I .11 E: H3 HIII‘IIIJI CH CH CH3 Br 2 5 + ene nti El mer GI E-‘JE1 J-M..J. Freer-rm, Berkfilau, Cr». Chem. 3A May 21101. Final Examination Page 9 of '15 .‘r‘. { 1a Paints}- [a] F-‘repeee a reaeeneble etrueture fer the ergenie enmpunds belew that ehew nnly ene geek in their 1H NMR spectra. .I' Anewer: =3 {ch Hew many peaks are in the DEPT-135 13: HMFE__5peetmrn ni: " __:-~__ I 3' Answer: ,3" I“ I ' _.i [d] Prepeee a structure fer the eyfl hydreeertuen EmHm Min—[he fellewing NMR spectra: 'Nflrmal“ I ‘IIIJ [In] Hnw many peeks are in the 75“IE NMH "ne_nn_al" EpEetflum ei: '~ x — I 4:. 2on1 ._l M..I. FrEhe1.Eel'nul=r'.C-J"- Chen-r. 3A Page 1|] of15 May EDEN. Final Examination 8. I: 15 Points]. {a} The addition of one moleoule of HEr to a linear termlnal alhyne oan prooeed in Markovnikov or entivMarkovntkov faehion depending on reaction ooholiliono. Show the products ofeeoh type ofaddition in the respective boxes below and explain eiearl'g-I how one could use a single ml: NMH eaperirnentto distinguish without any ambiguity one product from the other. HBr _ R --—e on —s. nnrl'lr'sraolmlnov {Ft = saturated alhylj Markovnr'lrnlr --n—_ ! Explanation: I. Ed {m Fin unknown oompounol with the moteoular formula oqnsogo: has a strong IR bend at His cm" and the 1H NMFE soeotmm below. Wr‘rte a clear structure II'or the compound and assign all peaks using arrow-'5 to indicate which part of the overall structure oorre'sponds to eaoh peak. at 2001 JM J. Fleet-tel. awn-elm. Ctr» Chem. 3A little-grr Eflfll. Final Exeminatifln Page 11 of 15 9. {1B F'einta}. [a] Frepeee a sten by step mechanism fer the fellewing reaction [shew arrmve}: CH3 ' __ I. CL. S. J t = l .3 cm IN "H ' ,N —* {3H3 DH e143" CH3 r II .-- "' EH3 - 't ' a _ Ill-1LI ;___1-'| I H;- "H. H .-"'I “HR 5' a“; .-". ' -. 5""? "d- I _ 1 _ II "' _l ', II ““H._ ' m .-" l I f F .F _- I'l- ~-_-- “I .J'- ..- f IE “3-x I {b} it Ihe chiral center at the starting material in the abmre reaetfen had the 3 eenfiguratinn. ahew with an arrew where the chiral center at the prnduet weuld he. and indicate and explain what its ahanluie eenl'rguretien would he. CHEUH /l{IIIEr 'h' CHECHE CHECHECHa ‘EHE 1 1 Tsei t pyridine I "qlllflH ‘n—h. HAD 2; eHaaE‘ iii-2331 J.M.J. Fr-Ed'lul. HEl'kfiIE'II', GA Churn. an M33: 2001. Final Examination Page 12 cf f5 11). I: Fflints]. Elicia-hexane: perD5E a Di: H {blprupnsaasynthesis {11" MW: {mm MWEE [c] Eumplete the fulluwing reaction shuwing the missing reagEnts [saueral Si-Eps may he needed} $15-51 J.h1.-f.Fr=~:r-ct_flelhu|u5-II:I-_ Chem. 3 ' A MayEUfl‘1.F|nalE:-:aminatinn Page ‘13 DTTE I'- s; I'i . ace" _.-'\- 3E3. a": H .-"' Hm. III. I“ affi- "— I" !1 .-I-" PW. I If; '\-\. | I; .. I {I .- Br EHzfiHg 5 I " H'Fm Er CHEEHE f: .-' .-" H n I f- .' fin ___..r-k J a. I _fi} .rd " _ I' I I' I n .-' _ ' _- f 1 -. I — —'- '- _- _ (JEE- __.a-\. --"'I M -._ 2"" I Eur“,- lw. _ _ ___ ___——'—_ __"'\-\.h_x {'3‘- fi _ _ __-—"‘- .-"' T. . J I‘- a“ I _ _N i «___ 5 , ' _ I {If 5- a- - J I -1 'I 5 r'r- II. J- LII:- ffl-H _ _ __d___—. _#_._———.--' -. I ax" flag ”fi RW’E 5 .-.I__.- Ellil'lif-‘I ff: 5 r r I _‘3- I" H“ “a :L'k—_ ___: h a _h In. I _ “HE. '\-\.._\_\I II I'll-I'- ifi‘a -- "H. ’11.?” RE- I I ” I __ . _ | ,--"-_., LE: {’5 a a? I r I — — __ “HA. "I l r . .-I I 1-H J gr 5 a A“? x x " ‘- Il L _ xxx-{.3 “Hf/.- Hill I__.-___'—. ___ Earl- H “I If Hi If f I: _ ' I!” H I ' '~-~..._..- .9 43 I.'-:I Fm‘l .I.II.I|.J.F|1':I:h.sL 33km. Ell Chem. 3:». May 2W1. Final Examinatisn Fags-14 uf15 12. I 1E. Paints 1. Pmpsss s synthesis sf ths cnmpuund bslsw using sns mslssuls sf ethane. and NIH mfllssulss [If prawns- 3142.6sz CH3 59- T-f- '41 _-'. {THE—'1:- E I; -"| II'll- (3—: CH CH ’" '“EH 3 '2 E D 3 f I I: .I I . _ _-» {as [r ____ ,_ H _.|r __:__ Ir || __I:_-' Hi fig; __ II .-' _ 1. |_ an. ‘__ L _ If _ _ (in. I .L .a-I- _ .-' I _ _ I? I _ .-' —_I— ___I I {HFL —‘- ; _ is, L' ‘ “ | I II LIL“ L-i _ C E I: _ I. {PI-I. I.I i“ [L _ '-I_"J'-:L'I|—r'" ' I I I - q. ' fll'ihl. _I '5 P LIE-r“ — pl; l‘ I. I_-_. Llllfit‘fr-I‘r [TEHI'H .51" —I.3—-:" I’Fi , _ L.‘ f __.-1 7. - r I: a ' . RE .I: IIIr—hr-EJ 5—? I .r" '- H. II q—fi' -fi—- "sftl' I-_ _:' s g”- rug—p >—*-‘-L- ml -5 ~___.-r _- xx If; 3' 'x_ -.I l,- u; ._ [II .5_ "' a I I 5—1 we I " LI; mi. LI“ ' ' .. .. —_J ._/ “Nah Pig"... / _,_"-'II “- II. in, ._. —.h I:- I E-II'I'JIH J..'-.‘l...|. FI'l’lIZ'J'ie-I, Elrkfl'm‘, CF. IShem. 3A May 200‘]. Final Examinalian Page 15 at 15 13. { 1T Peinta] Censid er the tellewing ether synthesis: GHQ—{jai- CHg—Elr —-_;.. 1:,H3_fl_..:H3 [a] Name the chemist whese name Is essectatett with this reac1icn: [tr] [3er the Lewia-tiet structure at the precinct ether i q I HI a I“. If; _ .- l— ,. .h _ . _ _ t' _| If" ..1 tc} What is the appi'cxirnate B—Cl-C trend angle in this precinct [circle the tetter attire heat answer} sat-t " {at tact is; 120° _'tc:i::1trr= ta} an" ts: are [P] Ncne at these . e t-r’ - [at In the ahave reaclian GHa—U is classified as a {circte the letter at the best answer} . —H..h I_.-"' tel atreng electrephiie {B‘Jwealt elecirephile :tgiletreng necleephila [D}w&al-: muclecphile [EJ strung acid [F] weal: acid {G} neutral SPECiEE {H} leaving grunt:- te} la water a Quad ealtrent fer Ihis reacfiun? Answer: “I I I I- I.r' Ernie-"H Fun: '53 E: if} New caneiu'ertne reaction: CHa—DHCHE + Hflr —t- CH3_'CEJ_'EH3 + Er El H I t 3 , CH FD-l— 1 . What '5 h mnlamlflrflhape flf 3 t CH“ {Circle illeletger afihe aestanawer} H . x“ I“! .- [El linear [El] bent {E} tn'genalclanar rift-JJ‘E'trlgehaIF-ytramia 1E1} tetrahedral '-i._.- P5. . {Q} Wrtte the equilibrium censtant fer the reactien EHEGH + H21: -..— CHa'D + Hal}1 in} Git-en that the pita at methane! is aha Lit 1a which at the teltswi_ng is clean at tc_ the value at It in this reactien {Clme your newer-Lana I ’ ~t flu-H. «.1. I-_. is} see te1+1e {Ci—1E Imus-‘5 {at retiErFi 1.Et:‘ll:l'13 ta} TEETH-HE I‘M—IKE |.-' '- |.- .- r..r_.« -- -"' - "“’ ...
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This note was uploaded on 02/16/2010 for the course CHEM 3A taught by Professor Frechet during the Spring '10 term at UC Davis.

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spring01-final-soln - I":i"lemistry 3A Spring...

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