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practicetest5_08 - PRACTICE FINAL Chem 322b Spring 2008 aw...

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Unformatted text preview: PRACTICE FINAL Chem. 322b Spring 2008 aw? . CH3 CH3 . Ur" C W Z g' I 2. Describe the most accurate relationship between the following pairs: OH I 0 O a. , . O b. n _ I! O and ch and /C\ - HZN NH2 HZN NH “W .3 ‘ ‘ d1 ’ ‘ .41” ; r (“9” J a fififi “mg a cwf ... W53; Ci 6 d. CH0 CH0 and 1 H I OH . HO H HO H and H OH H ‘ OH H ' H I’WSW“ m (m CHO CHO JWKWW .a ‘ K, Vmw flifi $445” M55 x gflfi'fikfi I) 1 H N , N -~ - N .. N EN N — N ‘> d I ‘) ‘) and I ‘) A‘N N an AN N 2%; N )m N HZN H HZN H HZN H HZN H 1 ‘flmv’zém! 2 2 % A? 5 ff “ m M + g NH2 NH 11. N112 NH: 1: :15 and 331$» 24} and NH] N If} H o ff —0 gr] 5 Wéwg £2250 ham“ 8 . co co . 1' H— fiH H__ *ng J- PhNH? =N—Ph and PhNHENHPh H— —-OH and H0— --H OH o . COZH 02H W . W, {yi- - “a, .3 (<1: ,1: CH3 + k. 1- - ' m. H NCHCO H and NCHC _ N\ and {Q N\ and N 2 2 HE 02 H H O H H3 OH . . « my gmfica m ‘4, W, Mfmaé 3, 2W 4 me: a»: m; 3. The pKa values of cysteine (HSCHZCIHCOf) are 1.7, 8.3 (the SH group) and M {£8} gas We draw/(r) Care, 4.; NH; (5") 15¢; Ma cygmm) (303 10.8. Write the predominant structure of this amino acid at pH values of a. pH = 1.0; b. pH 212.0; 0. pH 29.0; d. pH =30 {<3} $c#2c#6~flg+ Cage Cd) fisWyEw/éjcfdé e. "'Calculate‘ 6 pH at the isoelectric point (the PI) Fir :- ata) *PéfiCéD/g a» g. a 4. In---each of the following reactions indicate the type 91' reaetien ineiuding symbel, where applicable‘ Examples: (21) (IE—1301i + CH3I => Cl—gOCH3 : Nucleophilic alkyl substitution (8N2) (b) CH3OH+CH3COCI=> CH3COZCH3+ HCIBase : Nucleophyfic AcyI Substitution bass 3- CH30Na+-QCh2& —--—'=>- - O—ChQOCHS S b. O—ONa + 602 --—-—+ f” " 002 c. HZNCH(CH3)002H+ 02F —-~ OaN—Q_NHCH(CH3)(ID H N02 ' C’N-Pl _ ckrbH Magwfiéa Mm R1 d. R1002H +R—N=C=N—R ———I~ R_N= ,4; J1“ A) NH-R e. H——-N='C’ “5%.. nzmqomn- .. .HH ‘ . ,4! qfo I ' CHZOH CHafi‘H-s _ f . EtaN O - ‘ HO H 'Acgo WW 9“ OH ' am CH20H CHQOMe o Megsq, 9 0H Me O NaOH HO mo OH OMe CHQOH CH2OH 0 Br"! 0 h OH H 2 +5 OH HO HO OH OH 1.. Officw)? _0H‘_.. +N(,CHg)_a flwfim G? F9 (s) r’ . 4. Adecapeptide (10 amino acid sidues) having tug/overall compositi f, Arg, Cys, (Hui Glvaeu, P , T3142; Val unydrolyds gives:§/§10Wing fra%tsz @‘ sz. G1y+ Gly, e. Phe + Glu. g. Gly + Tyr. . Val + Gly. lu. Arg‘ ‘M—hu‘ What is the original sequence of the decapeptide? Show how you arrive at your answer. “‘“‘ V. , ,Pa’ég/fie “fig dcgégé @J‘é @ 5. Give the predominent product including stereochemistry where appropriate. If no reaction occurs-writer‘horxn’.’ a. ‘ __ .1)H. NNH. “’11. x N113 + Bmcgcfim.» 2 + 2 hfawcm 53¢?ng 2) H30 .13 . + F; W M/ Gama b_ H3N CHzCOg-I- Ph N00 ---------—> i c. Cigar-a0 + KCN + NH 4CI > 953 6*” figs;- My” d. ' “' Base " 4% x C, C (mkcom— +CH3Hexcess) “mm—r- )? C Lwfi H2 2 a!!!» 3 e. + __ base I“ (t—BuOCO),2,O+ H3N—(EH—COZ ———>. Aguog AW 3% CO; CH3 C9 C/{g f' HQHWNH(CH2)3"'CH002— + NaOH —-——-——--—-> NC («1/ 55?; “H2+ PLH3+ (1 equiv.) Wfie EtONalEtOH @c cg €015.73 Q. O—WEE + CH 3002Et ——-—--——-—b> g fifmhgk axeis (2 equiv.) _ ’W“ ALH Lfidz?fi#kiflgC;§ 11' OZN‘Q‘F + H3ECHC0NHCHZCOZ“ —“">~ 02N—{332‘ 2/3 c \ NH + , i + 1)0H' W t J, ngCh’fsz ‘ O—Ncs + H3NCHCONHCH2C02H ——#———-—-> (3 ,. cg I 2) 1130+ .... c C K CH3 5 :3 4; 1) OH EwNi'}+ HZMCHCQE i- H3N+m200NHCH(CH3)002‘+ Q—NCS ---—-> - ,— N/ a “a [ 2) H30* ‘ \gfi“ ~2' cg; ‘0 "Ch! k- O-Cl-IZOCNHCHCONHCHCOZH HE’Pd :- QCfi’g + Hzmcflr co W 2 a ém 5.22:3 bs do" I. 02 F + HgN—CH—COQH __..ae 02K)» MN“?!le i2 (IJH Ph “22 Cfflé N02 2 m- Q—CHzCch Jim 0 “CH2; (EH: c,de H ' + “130* EJH +- NH3 3 B {H 0 It a0 " r2 2 H 1;; 2 n. H NCHC H ——--———>- :7, 2 Oz excess a, - O OH CH} Base r“ m o @CHECHCO'; + PhCH20000I —+ .9}ch Q4 mfg, ‘ .. NH3+ fimgwflegfiy e2 1)NaOH p_ CH3fix;H3 + @—CH0 W @Cg36H—fi Cat; 0 . 0 x N \- NEW-e?" < 7. Given the structures of AA’s (HZNCHRCOOZH) as: Glycine (Gly), R=H; Phenylalanine,(Phe) R: PhCH2 and Lcucine (Lou) R= isobutyl, write the structure of : a. Phe.Gly , b. Gly.Leu and c. Leu.Gly.Phe. d. How many tn'peptides containing all three amino acids are possible? 6. How many contain two identical AA’s. f. How many tripeptides are possible in total? in I” I” (a!) 1‘85 (Fiat cw) My C3265; (A; JQN cgficafiaygfi (:93 (@119wa yé’ONMCfowA/ygfifiog ' (a9 fax CKJP‘ 8. Draw a graph of the surface tension of water as a function of surfactant concentration. Show the critical micelle concentration (CMC) on the plot. 9. Write reaction mechanisms for: ,V H 0+ a. RENHR' ——§——» RCogH + HQNR' Ofiwa}, #0 i‘ H.263“ f U z \ '5“; 2 f/ m jd R ,MHE’ _. 014 - fi 3R ’0” Mg...- Rxc” m E’KC/‘L E’Nflz 60” ’CN“ 1”“? " \fiue‘ "- 140 H H’on 2 *zjx§!+ . , 4. W fiH“o”z b HOC RTHR H3o+ HOG ——--——> H + ENE-I3" HO OH OH OH " ‘1‘ A A ' & ff? #3 t“ a? gag. i? Q @433 “a”; w/ all f} \Q'JJ‘ ' Ema \\b 3% 6H / O H U g 0. mm: + R'NH2—>RCNHR‘+ __ NHCNH I O (Beg-O g Q g 0 p: w? 43"") T 10. Suggest the Merrifield synthesis of: 3- H3N+CH2 C NHCHCNHCHZCOZ' from the corresponding amino acids using -- @dC 6‘2. y) CASE PgwMCIVJCefi #530 CH; NH... I‘mac W anyother needed reagents. H 0 fax; we Psnflwz O’QLCHZNy-vzrmacw psaP/yQigag cw: We W3”, . a .. fififim carc’wygnqfimm 9,3 __ HQ 9 h,“ 5; WW PSWCfi/gflg (#3 NW, (#N#- *5?“ W W ' “@47- 5’2’3 WwFMoc Wfi/Q Qfiswzfi' ~ 0.6 WW4: i ' $1252: '3) Mac: using the Strecker synthesis. b- céécho; NH3+ ‘ C #cw —» J N m . err-M W Qagzcyfl a MM Qffiffi {1 MW 6 Wig Hm <1} in c. Synthesize: QCH=C(_CHQ2 from CH3_and (CH3)2CO asthe only carbon sources and any other needed reagent. 9 ca fire/«Wat? C WJ‘L @cfi? W285 @f‘wg‘ “9* e2 «as “I s. a Wim$wmgf 4" W*” 4m MW «243;; “‘3‘ ...
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practicetest5_08 - PRACTICE FINAL Chem 322b Spring 2008 aw...

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