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ochemb-final-fall01

ochemb-final-fall01 - —:‘.E:cgen-Esch December 12"...

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Unformatted text preview: —-:'-;-::‘;' .E. :cgen-Esch December 12", Fall 2001 :'-:-“ 3'22: Final Exam Initial of Family Name 1. [10'] Circle and name the functiona’s g "“0 "1' in! V 0 i 2 0'] a. Indicate most (M) art-:1 least (L; acidic: M P; L— A _. HsN CHQCO CHSCOZH [Cl-:3)3N_ < /NH2+ / NH: I‘Tis I M53 -- NMe2 I . . . 3. (10) The sfmcture of the completely prctcnated form of arglnlne and the COI’I'CSpChdII’lg pKa values are given below: . {2.2) H,N-%—NH(CH2)3--fi:H-COZH +NH2 +NH3 (12.5) (9.0;: Write the cmrcct structmes of the amino acid at pH: 1.5 pH:-. 5.0 .. . _, r -.I raw “fa".(c\ -‘I3.rJ—C.~.dufc,l-el":.,>~-Obi-0511“ "3“] 5’ “I ‘3. I " f: ' I tdfiq ',v.L.~_ *NI-ll *3»: l". k .. J pH=10.0 PH=13'5 .1, — qua/cl ". —oH-<-'~3: I‘M .C.’ .. m5 ’ - I-l.:\I—(,~*J"~"'(C“".1]-C‘ "~'-\Hl\ “I I l' ) I I -| V ":1 n'HL I I2" I -.) 4. (20) Describe I'm: most act: we to relationship hem-con the fcilowing from the Eist: (A) Tautomers {B} | aearners. (Ci:- Anomers ID] Epimers ") Enantion. ers [Fj’ Con! .rm-ers ((3.; Resonance Forms ‘wfil-E) Diastereomcrs { . Identical [J] Diastc-rconzers iK} None of the above f,— O i- 9- H H b, CHafi—F_002Hb CH3N_-C “OC9H5 c C1490 H .| OK/ I. g. TOEH @H 0L —-r-~—OH - V0 ..‘ ./ 0 #0on a. how --OH and HO+ 6. {10:- A pentapeptéde of composition: Ale. Arg. Cys, Lou. ‘u'al is parrially hydrolyzed to give Ala.C3-'s + CysArg + Arg.Val r L.eu.Ala a. ‘ive the sequence of ihe peptide: show your reasoning: I. / 3'19. -- L 49 r (as , AM -« NM gw" N5“- ; j J i -_: . , .. .-| Law -- Alum Owl: - W'N "WU- f " :3 structure HQNCHRCOM of Alanine and Cysteine are as given (Ala. R = CH; and Cys. Fl = H) write the gructure of News 3-I.. got-.8»! l-i if H 5'01” I I . a l, l_ .1 I c, H .b ( * ,9 i1 7. {‘10} :1. Plot the surface tensionlS) of water against surfactant concentration. In the plot. indicate the critical miseile concentration (Cl-AC} f w -:3- p_ I. :15 I'J" if 'I‘ L 1” mug." «Kl..- J' u 6 190.16: “r w-'— * 6M0 : I M IL'Q'LLE“; , 95.1,“ b. Explain in one or two sentences why- surfactants are only eilectix-‘e in dispersing oil {dirt} above the Civic. , _ . . I . . "w'lQn. misiLWB 13gb. Lg 5min; ”'L‘ CI" CM LE, Calm. v.5 vim-9.5 .‘w .. I - ' r. “Jr-“@321 "" " x W- °~9b m-c -5 r" 171‘ W "K. J J {-54.4- ‘....~.'_. 5rFAdt-"d> we, no": -'-'.“9".' "70 q... zcyzcr lw'ula. “hull 8. {3(3) Write the mechanisms (curved arrows. fl Enterlnediaies including formal charges} a. s; l-" \ CHZCH=O +iNH3 E~ HCN -—‘» / \ ~CH2-CHCN ._ 1" _ l V r\-. NH2 ‘03-“ ‘6' "Q 14 - I - i I - 7:31 1" "Q/ rewshl-F CL; H —> ;—'L' Cal-g,’ .. _> ficwnjgfis. ._> '?L_-'C,'._J:..I— :n-n “ L. with * - ' n /!‘I’\ H . J, #5) _ Hr H ' 'r ‘l.| .IJ: " fg, iCErJ: .Il). 1;. ' '\ ' .rh . .9. . v3- ‘3“ fi‘~\_. ‘0“ land 01" .(- 5v“ .61 :34 as. 0- n‘l'é' Lfifia >’:F\>‘- ..- n'kfiw + ‘ v 3,. . .+ 4 Ac: > “H-4‘GN’ ID ~_1§ CH) 0-.) I. Ch: Gl‘O‘z ' 3 " (:25: 9. (45) Give the predominant aroducts including sierecchemistry where appropriate. If no reactior. manurs write "no rxn". A Qwrwg E, 5i3_.§‘;-N\//i . C“ _ ' moncnitration product <:>~Ng"z CI‘ —> I (6'9 :0 c. "1 Imp .. ;_ Q CI-15CI-L c02H ‘c—-.— 9;, arr ’ 0 ; ’- 2} Ni-l;3[excess)- 3 '. ,, “114%, + - s? {:I r; d. H3NCHZCOZ + PhNCO -----—-> IDk—NHF-ance-iac G 6’“ ’I ’3 gm -xi:;;v , .. y “I". --.__ _ '_ 41".; 63'1'9" i. C“. CHZCOEC‘IZHZE NaOkL .I-Hl_ (—3 L: "£45 {CA-- (fig-“36 'T‘G-‘u' . I I . H;ICO*C12H25 """ _" 6' 'O'A Y o A I ’ H90 A I . Ia; I L/ HzcozcwHas ‘ ' :-i4.,_‘-‘I 1* 3‘1“ 1‘7 a" "4" two products f / \ + I‘M? 1232' “(I71'x’s ho "a .1 II 202‘“ _ ‘ F :- H3N$HCONHC H2002 base ). alr‘r ‘W/O \Ifi>,_ I"! 1+6l-r 9 {1“ CI- ~. f’g .~."" CH . N02 3 R“, '3“ G CH-CCI-Ifi r I) II NaOH . f I 9 - ..H F-F 9-" -. ._,| :2 '— _ . , ‘, ‘ , " can .. I. '3’"- “LI. ..efi": 1' F'I 5 _¢I"‘- ¢ ‘\ h. Base /2 + — - CHI I {excess} —> </;I $5) a """ N 002 \ C' ‘ 10” n / HZ :3 I. ~-- g: .: : 1.);HCN M , .I ,H H H: :—---> ' ' .. :' '.. I fihl-LQCHJC‘ 0 )SC‘\ 0 . pooligCC1‘-III"'\I§‘@‘"'W . ., 2] H2. |\I, pressgre ____,_.\ .. j, + _ base IO \N—Jf II a (pBuOCOhO + [email protected]‘l-‘COQ 51% 0‘4 ,1 o _0 (on '~_ It I .. \ | I'_C m- 5‘24» 02-23 ‘64-; ’ H. . _ - _- a! IL‘, ”CH C‘J - k. HEN—C—NH(C|J.2j:-_—CHCOZ - NaOH “1.4 - f: , '4- \C V H I . (one equiv.) MI; I-1 In} NH?!‘ NHZY I /—'—~';"\___ I. — cqucozH OCHzogNHCI-‘IQNHCHECOEH -- ----—- {gfig—G 0"” (”Haw- II | II A00”, 25 5H3 0 O ,4, CH1 3 . ' ‘32:; ‘7'” E-.0N -EtOH {-3 P I. K’W 3E1 ' " a: II I m- OuO—EFW'L CH3CO .EI —---———--~+ ‘93—- 0-0410 '39—- f‘; I'equiv.) ' + amass 0e, -. r -.. . III- . < >< n—BuLI Q..- -. I hClfiwn “.04; no.4.) I 0 ‘iII baggII-IO fine-'41“ 35': Egg 0“ o. .' ' - ' | l 1 I O3 )- E: 2) Zn AcOH CI- 2 products .5. (in ."--' aSyIItluesizegeucine ((CH3}GCHCH2CHCCQH) s ”Elam ”M00 £1): and“ l n cfiu. o '3 1- 4- I-' , , _ c;-L:C'r'.-’I’I16|~ . ‘HO'L; . “mt-"Kjrbtv 'IN“Oe/+ a ”INCL. r. 4- H—9 ~ ' a '4. fl '\- -(_.G-"'1'-_?U 21'9" .‘I .r )3} Q {I ‘ ff ;‘ 11- 2; .2)?" 3...;f‘ 64'0—0—C’ -- L-GEJ 3-131“: #441 A | CH. -é/H 0 “a" U :2 I I. II n ‘ J ‘b _ f ‘ . 6* ’ - . ( ..jr‘l, A ‘+'n"o-C# U 02" 'JOU' ”L, J-‘* . 0' ”1411 b V &9 1 H ",‘> II' I ' ’9 5-:"(03 -fl_ ) , t“) _,. ._ C 5-. - 4“ LP 3» H'O C E C ‘OH —-—fi> 0 2“. 5H" I cgll'l- 'i C‘- ' LE“ “15"”? .. ..;," I ‘ I ‘If 11—. ("“3 c .67 )‘C-a *b Synthm NHchNToozH lmm'fimmmmwmm tab *5 - ’3 I 'J ' 0 Ir :? 7)"... I' [T H j" 3 u: - "..I - |_“' .1 HHS—c-1449? 4, fy—cna—u-o -r.'. > "L4 .2 o... n c 1 ‘ ‘- —r‘~ H (,0 ' ‘f {c.3513 " I \a " — ,' . 0 x h h < 21.9 F‘ (IA-CH1 c-dkha": 4430410; lg cm :x o q 0‘ If . : \‘ 'I' -",. I Pk-FC/L‘ J C/ II‘JVCH 1:,NH', 'I+C’O:'L H’ r} ' U_Jm§' | 3_ IE) CH:5 > “1 0 '-.'!‘~-. (I: (c i_._ '— “r. ... 'Lv loIJI ?' CJJ Cu... .2 / ..- Wmm?mmmgm CORK” 0 ~ 906 N I C,” I. G“ O IC’I ..__ mug,- - , .-. _ IL_ _ ...fi~ , :I ' , «A 4. 0H #3? C: 0Q» >1") -> {+1.}...C _CH3~- Mir-O'OLCHJJR O 5 .. - H : HR, 2. . g-F’R'C I41 .5 —c-r,.1,_.L,.;V-,.,c43~1 4.; —. 4‘?L.Cl1q—C/I' .. 52‘) “F _ I O :4- C III'}~:..T'5603'.I moi-4d“, O I " f 5 I. "~' ‘ \ . 'g .4, r I- 4 -O(,FC,"!"'L"C,"=C"'_3M “x.“ '. ’ f—{k-Clia—H / 'UUPH" - > .— zbk I .- Doc] ...
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