Chemistry 3B - Fall 2002 - Ellman - Final

Chemistry 3B - Fall 2002 - Ellman - Final - Chemistry EB,...

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Unformatted text preview: Chemistry EB, Final Examinetian Euldcnl name: __ Student eigneiure: ERG—:1? The name fir Lemme finly: |-~-"I .'w-lnn{ir1_'-'. December he. Eli-III: Fin-:15: write yen: answers in [II-c. spec-e5 gravid-ed- . . Plea: make sure the! :he exam hue: 15 pages: including this one. 3. “Tire EI:E'.F|_'~': Eligible |.'|T embigunue answers '.'».j'L] L'ue tuneidejed hummer- 4. Duly -.1. min]; :iltzplenients are ailuwcd [En {Talc ulmum]. Tutm 1]I?‘«£1-]'l:'.HTDDIf' 'l'AELl-T 'I 1: III N v II . Li He 3 c N :43 Mg .11 51 P H. -_ CH [IQ-.1 C1”: r15 ‘L'I Gflfll} LUCK! u:- U1 . I-~-| I 2-C- I a“: 1v11 wit—I Hi: E1 Ar - Et' Kr 4n paint; fifi paints: FJU pc-Elue 2i puinie 3:5 pflilltfi 3|] paints: 3|) paizfis 3'3 mine, 3'?! Jtil't-irllti | i Emil-I15 1:3 puilitfi 3fi1| mints NH, l H1 (CH-cum 1min: 5% tHr-a CH --EEIDI-I Illfiiflfl CH1— CH— EH—cc-m-I “tin: 531‘: 2% EHL—CH-Cfit— CH—CEI-CIH hut-Jr: 9: Pa“: CH;EH1—|:H—" CH—CUCIH balancing Eli-I: CHIS—EH3EH1_ CH—CGDH mfifianim: L‘H. J, _ :1-1; ~“Na-r a | r— EH -CU-:IH ’i‘“ EH fl—CHI— :H‘cunu 1:; TH: mfiqz— Ci-i—L‘CIIIII-E WHH T?" HD-Cl-II— CH—CGOI—I W? 3:14; CH1+CH— fH—cnnn EH: i-ISEE-Ir iii—EDGE M “I”: TEE-1‘ ,I—Ci-Ign- CI-i—C-SIDi-E 1:; 1': 1 | th'w'fufi'liz— 134—5133 .13 I~~':—I= | 123H— C—CHg-r CHE— EH—CC-DH I” . . I I HU—CI— CH:— EH—CEIC-H I HID—'3'" CH?— Eiil— ICE—EDGE HEN—CHl—CHl—CH-l—ZHE— CH—EEIEIE-I :93 NH: l- | HlH—C—HHFCth EH1—CH3— EE—I—E’Z'EII-l {1" [I j “IIEN'Z- I ll -“.d:|:i|r :.'.'| r~.I:-r= Hfi I L ~E-—I::I-r1— EH—EDEIH MEI Elllllllllf [[3] EC} IL: Ht: ' pmiin: phtnylntanin: Irrfllcphnn l-ETer: :lhr'::InEn: ryflzlm: lyrnsir: Han-'39:: :luflnliu: 55:31:: acid glL-llmi: EEI-i] lying :rgc'uin: higlifi'ia: .'-| .r: “1:: I III1IIIII1' [[1 PM! TI? 5|:r T1" :1:- ca; 11 E. :‘mswcr [he rhfl-mu'ing qucsiinns. Every 1m“: ru_: answer cancels a cnrrtcl anSv-‘cr [41": paints mtai]. EH}. Rank 1h: simcmres H'Ufl'l mus: acidic in lam: acidic | E = mast milk. 5 = least acidic] {S puintsj. CI D “3- C? :1 c3 A‘s- ,JLJEEEE AH JJLVJLHH mg Nit-135- ? “63 E}, r??? FEW “h r”? EB; a: h—J {In}. {Tim-l: 111:: uompnunds that upun treatmrmt with [13H2— incumurate 2 E. dtuluriums IE IH‘IEHLEII- I, r3 /' / :1 '- _, c: ' Eigenxmm II" Exit-“13E? 1III] I.“ Ella _ _ d. "H... .-'" -\.-_ I l I._ -._ II: ( , w ".- r" 'r J T- -. ' E‘h__ ___.-'"l 4-— HI} | -' _ _ -__- 'q‘uf'q‘h‘k .—- __. -\.___ :._:""--..H-__-\. {c}. Circh the IL-CHTI]: uunds Lhat are mam-mix; [S paints}- I_-_ _'\. I71 H , I” [L1]. Elm]: Ihu amino acid; [h.-11 wulri he synthesimi by Ihu Ea‘nrlel aminu— acid 5}'rl:‘.hl::ii::'. mnthnli L-;--. with flitUfll-CHE‘J‘Juh [E [mints]. .o——-. _.-' H .- /- _. H I _ '.-' III-H.- {L}. CirLl: 1hr: C-EIItJFEEIIJJIJL-i than gin: an all}? :Htcr :25 um: DI" the gratin-3:3 Ugmn mauliun wilh Ema ,. .-. . . "' a—a-"H l' ' .- “‘--r"- .I 2. For each 0:" am: l'ul'lnwi ng rcaminns. supply: Eh: rrzifijing ruugmts c.1- mainr nrgani; pruducl 'l._-. [51: 5pm.:- prm-iderl. I1‘nu reactiml 1'5. :hpfifln‘d indium-c by NR. {fill} pninm [UTEIL 4 pujflfj aach qua-grim). Flh _ _| _. , — 1- .- '- I-‘i’lré- I a L! a n _ 1L NaDEt [2:15 equiv), EtflH 3K "a ' In} HIM-"l;- HDE? — " " ' Waff- gfii“ '_'..-I- then aq. werk-Llp C '-r 1:» ".i -:' 1'“ fl_ _-: I_.'a'-. LE .7"; [C I LL HED, HyN-Efl .UH [t—EUUEC}?~ J‘- a. a, '— ,c D [d] FrnzucHH fl - -- 'a # H NH? p:|:-e-:I-:'.I.'1E EDCHN.,V,,» _H_ J —.. _ __ l I! | I - .'. ' V1: H '_| ' I UH. II. I'd .- "'{i I" |-_l- {9] H_.—-" 3 I '\-.~-\[I__NHE H's-‘- EA: 1 I:ng {h} m ELI" NEDH. HEU. CIE [I T” “NHJ .-' _'T I'.--1 -" - “a! xiii-RH.“ a .1” CDEME' 1'. _"I L + i: I - -—* aha H'H -.._\_ .I' _..- ‘- J.-:' VL- ‘I" h” E} a: . Hie-fli‘fi'h -' H 1 -" r‘ n . rL'Ej-r', Lilru r |-.-.,«* a | x H . i. 21-" i i_ {m x D NaDE—I, 1129.3; ._ _.-"' Ta“ | _.__ . r | 5“ LI: a} c:":. ':- _.. L4," Hf“ .ng LWH‘... than {I} j C'H EI-iguefluswclrk-up PAH-L. M I -I1. {m} ET; “Hx .DH n. .n. .-" 1' !__ I I W I [W l I «fix 3. I-Ipr euL-n n[ Lh: Jullluwmg reactlnus Supp-h.- lhr: missing rang-2mg ur majm mgani: pmdum in 1h: spa-2e Firm-med- [an raactann 13-:xpuc1cd Lndlcate by NIH. [fill] paints Ema]. I5 mints each [mead-m)- 1. H35”, Hg; 3; D Cl i! I HR. 3. fix _ “J !-.' {a} " “Oct 2. MeNH... EtCIH, I fl NaEI—hCN _ fay-f '- I. I E- - .—-.-. :I- ‘- Hfl’f — _-"'l'~\._.-"'-II {b1 } i“? |_'n. *3 m . '“1 If. 'I\. “23' :1 "'H. l' let-III. ._._I t.- : fir I _ avia- NH: 1. Li.-|3-.I'[DCH(CH_«.}3J'3 'r; .- _ than equating wafk-‘Ep 2 HEN. NH; JR kw; EH3D+IHEU,J ' ' I {H I . aveng- . Ila} it]; h “MIN- f:%__.-'-l-HHE I'd-1- .'-L _ a | Lag? “as?” ‘J I-‘.' h fear. fix .4:- _ a - 34:..- r. nih- . Ia III-H 5 _ M 'H. I I'- (He'd-Ed- __- 1—: CI Dr; II. “ "-' H. . _, “H- r_ I .--’ he" “fi—I 2. _Et2|:uLll than L El aqua fiU-‘fi WEIfl-znup :' {En - .. {I r [.h; .1sz g puma {11L 3:?" E El UHOuswnr -u if r 1' q p flaw; I I _ ' I . I' - -' .— . I tail-II: .- I.‘ . I 5'”; Illl 3- MECIH. HEI.5.ie1.rEs."._ II _ I _ _ ____': A; “a: 1.: :. .—_I . llll ;' 'T_. . __ J. L 1. was. Iw. SCI... ; I: .l I '\-\. in. LiAIH; , 31:. warh-up 1. LD.-'-‘-. H - r, - L_. if H: 2. F'h-EHEE; \Tx- my: m5 3. F3CC-33H ll F‘l‘m-‘ide a rntuhitniam fur the bclnw trartsjhnnatinn [15 puimsl MED a; a. a Mega-5’11: ”“\| FLC'H. -_~. \||/ i — - - - —|- "'--..H_h__._-_'_'.'- __- HmiJ-I-l I \IV ,_ _ I TEEN ljrpfl {IT reacuun |'.1' called the [-‘1crEr Epingler maflmn and can ha} | usurj [n 53nth :fiiTn: nmrphine. vicudin and related mmpuu nds If I,_- n . *T’w HRH-5f} __J :15! “a. I 'l. 'I :l'? I__.- “'- H .- "- Flt-5' .- '. II. I_.I H‘- EH. 4 I _ _-»_ I i l I' L b- 1 r: .L -.._\_ M ._. HE E H _ H “av-fi- . . 'LH’ 1 4 as; ' T .--' -. .I'iyl _-_-'- . “‘4 ’3: ' _ _ __. r i : _ 7F; J " II" n _ '53 : 1’ '-5 w - £5 1 " Pr «’1 fl" . «~wa L -~ .x - h v 3%; x E ||-. - -, . -- . + w“ “H ! fik-{Hhrflfll— H? .rll -i 77:“ U “a PH. L _. a", I ._ I/ I _; I' ! I__- | 5- Dnlm EstErfi are used as ymtecting gmupa 1hr est-3m. Frm'ide mozhanism fl}: Lhc nrdmemr Lu cater Imnalhn'natiun shown helm-.1. [25 points}. DME D '- GME HE'D'F. HED :' EETDME ADM»? Ill. a "_‘_' lurk {3...} r. _'.I I I?I:L I _~'-'".-'. 33‘; _-. I. ‘t-L‘L "-| | i I L" I.. _ 1.” H i' Baa; -_ -__ _-- I -"—"‘-.L "E‘- __.-"'- ma. J. ~ ,5" x .. — {1' _.r .rI'_.'I a“ 55.. 1 ' - .' I. II n «.- 3; "IL-{fl-Ei : Ill l+ I :II.“ .-'Ir'_'E'-:-"' Hiram-“fit: .- "' “EH” 1.”. If H IL 'I". .-' 1 .___ ___.-" ’1: r I 1-" T. fan. 3 - r! I 3-4,: .__~ q, I: x ____--K I d:- ..__..- . URI: A; h. 1' _. I.1_.Efl|;. _ gull fl far-TI” . ..--._ I'll} \Tx 15. Provide E mechanism fin- [h-i' hclnw [mns drfnatinn. Hint: thin; ahuu: the relminnahip m" 111-; balmy- Iransfnnnaticun 1L3: lht; Euhinsnn annulaLinn [3f] minlgj. F“ J 1'- D ‘“ [II We NBUME, MEDH IE .I'"\- .-' - J ' “a .-. ._ I all; {Hui ' III-II. Hi1 ..-I J ._L a“. I ..--'--H ' "HT"? war I". .-' . :- __..- I __ I I Elf-i- ' EEH-Fflw" _:. :fiC-IIII III I "-."'-.| ..-' _ _ rel I '- _.-'~- I - I fill _ r. In ‘- E ' . __ __. H _ . | ' II . 5| .d—. ‘I" “Iii—- - -I —| ,r" dfl_ I ‘I '- I'II-II flag,“ 5 I - t‘ F '-|T :3 .‘j :‘i'filaa'. [\y #— ;jcfijrra'm .-' 'II n a a v C .4. _ | .1 1 r ‘3 1 t? f ’ “a a!” | II . "fl-H“!th "hf-J :- "1I' Ifil I II “H. II.- - Ir F “m I '3 I1] a m LI-‘E DE J L; I; -~-.-"' .-"."I. K 1 I I, _'. I .b’r' '5" HI I” “I 5’32 In" ' .. ' '[ E-T “Elfin”: a xflwfl’ E 4 LIFE-'1 a?! L5: * .-' ‘.'I'_ Prm'i-aie [he must efficitnt snlid—phzui: synthesis. fiffily-fllfl-e‘wpPhc from any muttered amino acids. [3E] paints]- Hard-I F‘- HEW '\—" II. Ca—u. -\.- l . r — I| II I i5: '1 L- '~-.. ,5? J #1:?“- _I "urge" Era.- IIM‘ (AI IL-f'_ : 1' 'H_-": LE __i- :Hfiv ——_.._._ —'- .- "£- J If. I'- D“ L.“- a L}.- ; 3 I _i._ an; H T I_ r: E. {I 1L__,-" Ill a“ .___' | Li: _ _ -- :' fl . I —H. ' — ‘2} ' fin H ' __—'—"' _.- ' r ' rr “‘“r’ J I a _J H“ I r: 1. _I' I. - _ P: L .I a ,9 ‘a I rib . ' _ "Hd—J' ll. r... "~. ' we: k .~ {a c H! :—: {H r. '7 —| —'—' —»> fir *w’w—mxaA fr- m h : r a .= ‘? I! ? Hark???” HT!" Era“ 3. £1. E In '3 L ? Raf-“H :. H - "_ _-: I'MV'La g,- _h'- . - a: HIE-x] ' LBJ - n.3, a? F‘e-r'}. _.-_ =J «J ‘-' ,r Eh I. _4 '—I .3" [Cl _rn'nf_ 1T._"__"J_ if ..-"'- {II i"1 ,-"' La" _.||2.— Frm'l'de 1h: mum cfli-cicnt synthesifi [3-H Eminw}. fluréarflx D from 3- equiv DF 1. _ fl.- a'i—H‘. L ..'-__H'h I !i i :L-h -. 1 __La- I' _-'.._ __—_'j- -.‘_ few-.5“ I_ L __.- av..- L _ L1.“ Hal-3.:- HH {II I - -_.-__ r: 7f 1- '.._ I' II I Hnfljfikgr- .g___,_ —- r;- I'I r -'."--' '-:.:-_l- ‘i. --'_-__I c H = ..' . "-'r:~..’-. '3, -"-I-*:l-- -“ :: Eh. F-H .-'fi'\-\.. — -'r - — I "‘1' "- II :I f T '«t J- m Err- ? v’}’“ca I.-' :H .-'" I'.II and any Either reagents IC'I II Hg?" .1 (Part. I'F'J'F-r :24. f“ ‘3'. Provide the mus: =lT7uic11t5yufl125i5 [30 points]. a r H “\Hfifiw’ W from 2 Etyuw Elf Haul-FE and 1 and anyr azher rEEIQEH'IES l? my; Cl E II 'II I I I . _ 'I-_' H‘- .'~J--l r": -" -'___--' f! x- x : .i-r II II; N ‘ . My" .. “a a an " . II 2:} I f T " IIHEIfHH—‘H TI} (HEW _ fifl xii-“'- 33-”? "-th J -- _.- Il'h“'~\.._.'._l;| 1—3 ‘ _F-,-' -..-I. “fab?” -' —_-'?..I r, Rift" :-' -.. !I _-' Ir 1" Ian—lg I -:" I'-_.'_q1":'-', 'T- “5,: _ 'T‘-. I' —4_:- !'I lg: ,a. _ _.-"_. "'~.‘\_‘_.-'§"“-x.c7!_| Wa_ I1__._I _- “XVI-“fl ' '. Jr' [a . '3 I.r-' ! ._ a. LI "muffl D' “Hg-“Lh- :. r ‘i .-" _ ____ — —--;r- . F" fi- g.» J: L? a: 15:...— _ ' 3&7". I_-'"-.. ' ah __ If: 'I: r’ I. .-' |'_ If“ If _--- III El. VJ '3 .II' x 1- ET? .-"'- _~— .._l.- Ev .- ;- "H. --' R .-W J Li» w 19,-. U” ,. {- "Wu-Fr .- = I H.511- EFF ...|.'._ -. III! -. I _. _. JI ' .' I, - vats-hf nai- a I . L3,me . I _ | !.' x -r -r KPH-Halal “RU-4? I. :9 Kill-Flax? 'fi‘ lam-F}:- . I j:- . I}. III.|'_-__ In ad?- In. The :3.-r:l-;1pr.;1pa:::1l:lnn.: shown bet-3w forms an additic-n prcrdum 1.'ciLh HEI that cr-zJIILt-IIE. [he Pfl'lfllirfiflfi {If an iunlc salt. Suggest a strucmre Eb.- liliti pmtiII-ac and a reascm fur ilai uxiszence as r] slelbh: mm}: [1:7 pn'InLq}. - - I I. I : —|_ '. F."' "' I .'| r- . 'I-' I - I I I.-'_'. . - a. l.1" I. 1" ax —._'\I- a. 1. .—_. — — H11:- 5.:Ir.I'I.-.-__F Fri-f...- {_- I I. .'"l' .-' - - . _" .-I_-:'_-. F _. —II _I _ _ “J I. II. I r” r , r .r I:-' I F' .. I .._.~ . . __ RE I Fr ! EL. 5: 5%. A. the 1]. Thu-I:- un: 11“: tj'pesm‘i-Iydrugcni HI and [im prtfitm in the [Hjannulcnc 511911.11 helm“- In [11: pmtun I‘CMR spams. m'n 11-:I1k5 an: nbsen‘ed. I'm-E Ell. —|I|_fil ppm and an: Ell 13.3% pan Asaign [hum-c was. L-LIEitJI-E-r J liflr Hn. Provide a hricl'r.1:-.;p]anaLiI:In in: :I'L'JIEITi-JTIE‘u-‘IL‘T [15 pnirfla]. .' .'—I _.._|_ I.J I. I _ . I I I I- . — —_.— Ii._ _ .H-_ I _ _ _' _ I — _ - u-x 5'4: _. 'E I _r_l .-_ r .-' r-": ._ r]. q“ _- E I {If :f_ . I .-_.I.-'._I.I' I_ alt. I. I' I _- _—_ I I .— I _ I | I. _.-I . “II-I7 ’7 "- inf—"'- ""'- F.‘ I‘ r I r'l. .- . In: c'-"-.-,- t -'.--e ram-"tr {ix—“T 1": -—~ f . ' '. " . v .. _ . _ .r . . r -- - r- I - -.»- r -- r»: :.-a- n: a -: r - 1" r ’ -' a _ __,»'...-.. ' ‘— ' '” ,9 1'. ...
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Chemistry 3B - Fall 2002 - Ellman - Final - Chemistry EB,...

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