Sample final exam org2

Sample final exam org2 - Organic CWHE Final Exam 5 m i 5...

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Unformatted text preview: Organic. CWHE Final Exam 5% m:- i 5 Name Muhiple choice questions l-SU, 5 points eaeh. Place the capital letter corresponding to the eorreet answer on the line at the left of each question. 1. Which is a correct name for can:agnosticttnt:HatersJ Hit A) N-ethyl—E-pent anatnine E] butylethylmethylamim C) N-ethjrl-N-methyl-l -butsnamine D] ethyl isopentylentine E} ethyhnethylisohutylamine‘ 2. Which is a eorreet name for A) 3*elflurop31'imidine " ‘5 E) 3-ehioropyrrolitiine C] 3-eh1oropiperidioe D} 3-ohloropjrrroie E) 3-ehiorop3sidine 3. For oompounds L, M, N, which is the least acidic? H .r'" l €131" Ni: ' E HN+ Kiwi-J {In L 1i M 114 N h 4. infidaznle has a pKa for its conjugate acid (intidazolitatt ion] offi.8. The pKa liar imitiazole itselfis 14.4. At a pH of 4.6. which of the following statements is true? A) The major form present is the imidazolium ion. ,r E} The major finnt present is imidaeiole itself. C} The major form 1present. is the imidaeole anion. D) The itnidazolium ion and imidazole are present in a 1:1 ratio. E]: The imidazoie anioaand irnielazole are present in a 1:1 ratio. 5. Winch of the fink-wing statements is true about D—glueose‘? _._._.... A) D-glueose is a heptose. E] D—giuoose is an aldose. C] D-glueose is a ketose. D) III-glucose is maiahr in fisranose form in solution. E) D-gtueose is a mmedueing sugar. 6. Which is The correct Hawerth projectien uf’fl-D—eltmse'? H e- H H Ah Isuzu" B (:11an c CHEDH OH OH OH 0 OH H H 0 OH H H H H H H OH DH H OH H 10H CHzflH CH10H DH Dam“ Km! 0% DH 1;. OH H E H H 1'. At pH 7, which represents the predenfinant ferm of aspartate in sulutien'? (pKa Ivalues for aspaflate are 9.32, 3.315, and 2.09} 0 fl 0 0 fl 0 1| II H H _ E “30. HUCCHIE'HCUH 'DCCHICEDH fl CHgCI: A. +1“ H3 B WEI-H; C m '13 0 "R '3 ‘3' HogCHgfllH’Cfl' _UCCH;{|:]'ICU- I:- NH, E NH: 3. What is the p] value for aspartate {see prehiem T for pKa data}? A} 6.34 B} 3.36 C] 5.26 D} 51%: E} 2.93 9. Wh amine acid below wnuld be aimed last, at pH 4.4. from an inn exelmnge eelmnn peeked with a cafion—exelmnge resin such as Dewex 50‘? D ID 0 D + I1 II u _03 I! _ H3N(CHJJ¢CI1HCD' CfigtliHCfl CHfiEHCD A Wu} H WH} '2 EH} bah: shire 35pm 0 '3 0—30- (31-12(30— ‘f4 +th D H; \H E 3 glam _1l}. w‘rfich ufthe 4 heptapep‘tides A-I} beluw eeuld gun; he the prhury stmeture efa heptapeptide for which the {allowing elm-nations were nude: i} Cem‘piete hydrolysis showed 2 T313 2 Gly, Lem $611 and His ii} Ednmn‘s reagent rein-amt! Len iii] A earbuxyyeptidase relewed T31 iv} In acidilifln to anfine acids, partial hydmlysis gave three peptide fi‘aglmnls Him the sequemes: “he-Ser—Gly, th—Tyr, and Girl-{is A.) Ifll—th—TYIhSEr-Hifi-fily-Tfl B} Leu-Tyr-Set-Gly—His—GlynTyr C} Len-GE—Tyr-Ser-Gly-HESFBT D} Leu-Gh-I—Es—Tyw—SeraGIy—Tfl 11. With structure is fi-valerelaetene‘? CI fl 0 ‘3' .3. fi a fig /\l:f A B c I} E 12- Which structm‘e is isemwl hutamate'? o e e u n n p. (CHthHeflzeeenzeHzeHg a [CHgfiCHCflCH-JZHICH; c CH3CI'52CH3CGCH1C1'KCHJJ2 e D II II n CligCHgCOCI-IqCHmth E engmeeeme [43,}2 13, Which structure is pheny] hermate? D ‘fi' ‘3 '3 E} e PIEDPI: PIEDCPh P117350 PhCOH A ‘3’ B C n E 14. We}! is the pro-duet efthe thllew'ing reaction? a“ H a e- 0 o HCI. H20 u E“ XC " —- t! A CH3CCH=CHIGH 3 CH3 [-HZH1CH1IJH Hale I-IECOL‘H; CI 0 (II: H II C CHaCH=CHCH2IJH I] Cl‘hCCH150H E. CH3CH=CHC€ICH3 15. ‘Wlfich mammfl E-I-I is least midis? 0 fl 0 D CH3 " a O 16. Which isthestmcture fifth: major prodmt‘? EH30 0 g 1" OCH; ,3, CH lab—Cf 50C]: 30H m4: Fla—CH DH A OH B C' ,0 ‘31 OCH , 50C} Fri—c" NHL” 3 syn—c" C «3mm3i D by; E DUI-I3 1'1. Which is the fill-nature offline majm pmdmt‘? fl 0 H 0 0 G H EWHCUCHJ HCI 1| II II CH3CH1CH2CDCH3 _——p —- HCCHCDCH; CH3CH2$HCDCH3 | Naomi A. (II-120113 3 cl '3' D '3 ‘3 '3 l Ii CH3CH1CH2COCH CH3CH1CH1C0CCH3 Cflgcmclucm c I) E OCH; 18. Which is thy: stnmturc flfIhE major produci? c. u MEET OH OH CHJCHICHZECH; —‘—" CH3CH2CH2¢CH3 CHSCHICH1ICH3 2}H30+ “wimp HEB! MEOH 1" I: OH 911 UN: CHJCHgCHztilJCHg CflsflthHziICHJ cnjcnzcuzalgcna Fh H DH (3 D E 19. Which is the soucture of the major product? o o CH iitcezhiiocu “HEBH‘ UH Em If“ I}? 3 a 2. —‘——'* CH CH CI—lCICH CHc CH CDCH 2} “30+ mm 3 Hi tile 3 3 HIE 2h 3 H- e oH on cl: cl: IR CH3 l-llflflghllflg c1t3c(cng}3cou CH3C{CH1}3CHEUH C 1" ll. 21]. TWhich compound is met basic. Le... easiest to protonntc'? 21. What is the correct sequence of increasing reactivity toward clectrophilic aromatic substitution fiom least reactive to most. for influence hearing the following eubetituente? A] ooze e e: c CH. e ocnj B) octt3 «2 oH3L e Br e cozH C) coin e once, e til-L <. Br 1}) oucH3 e Er e CH3 c (302?! E} Br e CH3 e eoJH c: out, 22. 1|tF-i'l'tich sequence ofreectione can be used to eynfltesiee m—nitrobeneoic acid fi-otn berm? A} two}. stod then Meet-30., H’; then (El-13:3], AlCla a) CHch MCI}; thee Neergoi, if; then END}. H230, to) Citch etch; then thoa, H1504; then Nazcrgo... H’ n) mob team; then Memo” H”; then CH3CL Ate]. E] Haiti-EDT, l—l‘; then cuch MEL; then moo}, ngo. 23. 1Which of the following coemounds would give mainly meta substitution in an clectrophilic aromatic Substitution reaction? ‘3 iii oiiCHj CH3 c ocH;L NH; A. n c p E. 24. Which ufthe fiafluwingisawrmctmfor: m A} muchhmrfltrobenmm B) l-chlomafiumnhwhenzene C} fl-chlumanflme ND: D]: a—chiumanilim E] [,3-chiomnitmaniljne 25.1nanelectmnirmaantmss spwmkahp-entamlisnnmrgjvesthe amatpmnfinent pcaksat mfz 1'3, 31 (3.1-190 fingment, and nfl'z 59, n flail-,0 fiagment? OH OH {1H CH3CH1CH1CH2C Hgfl'H CH3CH1CH1éHCH3 CH3CH1$HCH2CH3 Cl'igéCHzC H 3 H3 A I] C D .____2fi. In th: fiagmemation ofi-chlnmbutam in an electron impact mam fipmtnnn, which ion fragment would m; be a principal fi’agn'ycnt'? if: “cf: + + 4': Ir 4- CilgCHECI-ICHJ C H3CH2 EH3CH1C \ {II-th {fin-[iL A n I: H I} H E 2?. What multiplicity would you expect for the meihyi {CI-i3] Sign] in the 'H NMR spectrum ofdiethyi aha, CI-I,CI-I.,DCI-[2CI-I,? mush-1.3m 11}th C) nile n} quartet E} quimet F] sextet 28. Haw many sigmls wnuld gnu expect in see in me 'H NMR spectrmn of the fillnwing Gamma? fl AJZ m3 m4 DJE me EjiI} I| CH3CHCCH3 (he 29. Which «CA-[.201 immar gave the following 'H N'MLR spectrum? U U 0 D II II II II CH3CH3CDCH2CH1CH3 CflgcmoccmCHgCH; CH3CH10CCHILCH3}; Cflgflflgcflfliiflflg}; A E C I} M M 4.1: 3.: 1n 2.: in 1 .l 1.0 In M 311. mepwflufiM‘Hmm? Er Cflzflfla §H2Clizflr 'bHCHS :_ ‘13: A I! c .rru—I-I—u. mien; 3|. Whammdthebetterchcnfistryinmfld? A] Bustfln Red 50:: E] Haw York Ymmws 32.(lfi points]Forfl:cVi1aminAsmmtmc: Hack f“: m; 3 R “k IQ}: UL EH :1“ fi’ en“ en“ Harv *WUNH hflhfgmz mama mammfom usitanfinA‘? Howmyisupmmmfismthcmhvflmfinhme? Mmkafifflmeisupremunitsinthesuucm. Underlim the combat. term fin: Vitamin A: unnatume seaquixerpene, flea-pane, sestcrterpme, tritcrpene, tetraterpcm, pentalcrpm 33115 points] Give the mature ufflm rmjur organic pmduct[s] expected from each fifth: reactions shfiwn below. flw cm; L Fcfig ‘13]; ujc- —flH I{23"}! '1‘? fi’ Cm cu m Hyc" {1" EH] “Hr?” CHaNH: MN m' 011 Ch FuCI; 34. (14 points} Use the :13de arrow Damion (“arrow pushing") to stmw all the bond-mkmg and band- lueaking steps in the mhmfism if): the fiammtinn of Lupin hydrate fi‘um the “BI-hum ni‘gcranyl pyrophtlsphate: DH kaflxpfur Hf I K ' It hydrate 01.15 6&0 H20 rpm DH ...
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This test prep was uploaded on 04/21/2008 for the course CHEM 313 taught by Professor Forsyth during the Spring '08 term at Northeastern.

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Sample final exam org2 - Organic CWHE Final Exam 5 m i 5...

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