Answer key exam 3 org 2 07

Answer key exam 3 org 2 07 - Organic Cmcnfistty 2...

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Unformatted text preview: Organic Cmcnfistty 2 CI-IJvIIJP-IB Mdtmn Exam 45mm? Questinns L17, 5 points each. For unfit.ka chain: questions, plant: the:an letter onme to- the com answer on the line at the left ufeach quwthn i l. Whjnhis a comet nan-tron A} 2-mthylpyrazinc B) vathyfpiperidjne N H C} Z-Ethylumycluhem D} 2-mflqupynuhfline n 3 E} E-tnefhylpyridim C 2. Whisamrmctnamefor: {CH3 A] N-mrthyluxetm B]: N-mcthyhxacycbbutan: N C} Nvmfltylazacyclubutam D} l—nxtllylazh‘ldim D E} l-umthylbutaumnim: B 3. ‘i'v'hichisaootmctnamefor: C113EH1NCH1CH2CH1EH3 3‘] WWI-1W H} bufflfihyhfithylmfim (EH (3} N-«ethyI-N-meflnrlpnnmmne IJ} Nemathylethylbutauaufinn 3 E] intend—Heep:th ; 4. Fee eempeunde A—I} below, which is least eeidie? H. W‘if “# ‘ it L g; 'f # 3 h I- iimx H D‘fim EH 6 “ref! A [E] 1-1” B I“ C E:- I} U "[1" l... ‘r‘ flan—hes Maui-.137 Again“. “I. “mi 5 W aha-1PM A 5. For wuqmumis A-II below, which is must anidiu‘? 1 E 4t 1 etef 35‘- H M Pmim ' N W“ N speetee {memes (e 733;” if ‘5 [B [3 ML Mart: — " E i]: B c n 5L“: wai‘htfl? ‘- EMA pyMk’WPI. “" “Mfg—'1‘: “~le '4'" flwgg E’fliflufif‘ _‘B_ e. Imidaznrrle has e pKe fee 'ne eeejugate eeid [finidamljum ien} ems. The pKa fiJr itm'flmie itself is 14.4. At a pH DITA, which uf'th: fiJfinwing statctmnts 1's tnIe‘E' fl 5' A] The rmjnr farm preset“ is the imidamulium ion. ‘3 H” B} The major finrm mm is imidamte itself. :1 the mejer form peeeene is me meeeeele anion. h E ‘1 D}Tl:v: infifimfiumitmmdhnidamhmpmtha I:l ratio. E} The imidamleanionmfl iruidaznlem presenthta l:l ratio. a r H' 1-,! Jr 5.? flfwmw‘w “M31 .1 _ i 1'. Which of ths following is go; to: about carbohydrate A? A H.H It) fit) A is a pmtose H0 H B} A is an L—sugar H H C} A is a mmsaocharide H H D}Acanfurmapyramsering HIGH E) A is a mmedusing sugar C 3. Which ofttto following to too about D-maumse? A] D-nnnnus: is a kcmse B} D—msmmse is an enaminmer ufD-glumse C) D—nuumuse fem the same nsastmc as D-fi-tmtose D} D-mannuse is a heplnse E] D-msnnose is a diastereomsr of D—fi'uctose Uh 01+ £1.70 5; 9. How many upon-chain mcrcflisomcrs arc possible for a E-kctupenmse‘? # i u A.) 2 B} 4 C] {t D] E E} 115.- 3MP} D 1t]. What is thc cortoct Howorth projcctiott ortltc moottoso rot-m nffl—D—afloss‘? :3 OH (3 H tH‘sf-‘U t “10 B S OH HID DH 1 H OH 3' H OH H H if H—-- DH H H H H o" H DH LCHIOH EH10}! i EIJpH I] 5' '3' mi E UH UH tII DH CI D—alusc H L 3‘ H H E 11. A HEWi'Orth projection Dione fifths cyclic fizttjns nfD-galacmse is shown bolow. Which is the corresponding chair commutation? cHon 0H .0 an moon 0 an 01-1 0 Doghouse H on C 2H”: El EI-lgflfl m E J on Is] 0 .— 13- B 12. At pH 5, which rcpreaents the pradunfinam farm nfhisfidjne in solution? {pKa values fur hisfidine are 9.17, fifld, and 1.32] H + 'H' + M NH; N NH3 N 131-13 g1 ch 0— 41.1 ch 0— {A ch 0H "' N CH” + I .1 T I 1i 31 If m “if 11/ H N NH F NH F fin 3 x 2 _ r 3 I (ill-1'1 gChTUH 0 LTGH FL D D E U H F D Ir1 'L 5.3% qfl . dfndn cauh‘en «but «Mu-.1 Elimismcplvalucforhisthflm? C _ B A 1 . a IT A] 3.93 B} 5.50 L} 5.68 D) 6.134 1:} 16:) fl “_ S. j PH A [4. Which fifth: fiznflowing amino acids hasthe highest. pl value? [all shown at pH 1} HgCHgCHgC 02:: CHfiCHgCHflIIEHCOEH HflgflflHgflHztllHCDzl-I “m3 gamflflfi {warf— A mine B m C a: --""' {lul—mfip; 9F rKA Hindu“ fink fluid—11. a? Hub-n14" Ma Amman-1h. firuufi @HEHCDif “fur-n '1in 3W; 1- , 1 I (Pt—1'; 33;) I HIE.) H3NCH1f01H +15% [.1qu an .1 j [I Birch: r. W D IS.Whichami:masidwouldbeethedfirst,aipH4.fi'umaca1ionexchangemhnmpackadwflha caiiun—mcdmngc resin such as Dam SB"? {act pmblcms 12 and I4 fin’ structures} A.) glycine B] phenylalam C] lysine D) 51mm maid E} 16. For D—glumse, wrrte the Ilamnh projectinn of the fl—fiJramae form. Hflflii-thfl hW-fi _ LI! .- A [1 much ofthe 5 heptapeptides A-E below could be the prilmd'j' strueture ot‘a heptapeptide for 1o'hieh the foliowing observations were made: {note that amino ae'td sequemes are 1written. leti to right, starting with the N—tenninai amino acid) I") Complete hydrolysis showed 2 Val, 2 Ala, Giu, Set, org ii} Edi-man's reagent released Glu N" Erbium: iii} A earbonqaeptidase released Ale Cr. J—errn that, iv} in addition to individual amino acids, partial hydrolysis get-re three peptide fragments with the sequeoees: Val-Ser-Ale, Glu-Vai. and Val-Mg 1. I —' \1 "l‘: Aonu—ugi—Arg—fl—VALSer—amti --r'DM.lY dufiwh‘ {Li th'i'tcl‘lj Lt)+ ml} else 13} ate-Ser—uaJ—Atu—AIg—Vatotu I ' . C]Ala-Val-Ser-Ma-Val-Mg-Glu {:33 I“ “'0 D} filo-Vai-Ser-Ala-Glu-Vai-Arg a} Val-Ser-Ala-Ght-‘u’al—Arg-Ala IE. [8 points} Are there an],-r otiaer heptapeptides that would satisfy.r the information given in Problem 1?? lfso,wl‘tatarotl1c§r? ' [I'M—“fl gitaweSevfl— awe, attdatvfirrj—maer—Mf— i 19. [3 points] it] Write out the entire structure. as it would exist at pH 'i'. ofghrehte-Iyshte—ntetitiotfine {Gh—Lys—Met], showing a line for each bond [i.e.. C-IC, C-N. CFO. N-H, eta). Donit bother to try to show eonfionnation of the struoan-e, and refer to problem 15 [or amino acid structures. b]: Wow the pI value for this tripeptide most olosely match the pl of glycine, or lysine, or methionine? Explain briefly. o u o t mtg-‘Toatnisw t u + u H acme tea-a thwart“ tours (Eda) owl Hi4} “EH “M- mama: e our? “rod with... has-— thus. Fruit—H #493 flu— pifiLvaLm; 6;» jfriirtrhef H“L"i+ Li medial to. We? edw‘iw to bide; H fixtqu fMiIr-r yoke, {amen “tum imimu ._ 5‘ .- 20. {9 paints} Write the meal'flflism for 1h: reamiun of final: smith acetic anhydridc. anflain 1h: path-mac {our reunion 31: Lb: 2-positifln rather than the 3-position. Mac/LAM o1 AWN: mm; mfifié W H H {(3 E H H “A fl we; I 4 I F H 0 I H Mi... 1:“ W M «A firb‘wyf WWW EL “ix 5 if Wu"an Tm 43m MFHJQ am I‘ L :1 fl ( I: E i I A new heart W fiermMM “TH? l lacs a? lifl-l-rML Ha: rte—~an Ciflj [L CI; a. 1.5, “a” a -—-"‘v* QE—ca} + H0264? If I.. I h.‘ a” { WM mic—chmth din—i 'H-A— 1* Paiiq‘mfi HRH?— 3 Marc. MHWCL mfum 4* (“L ‘mW‘flli ...
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Answer key exam 3 org 2 07 - Organic Cmcnfistty 2...

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