322bs06_sample_final_key

322bs06_sample_final_key - cum WNW PRACTICE FINAL ' 006 1....

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Unformatted text preview: cum WNW PRACTICE FINAL ' 006 1. Circle and name the functional groups. Use the most specific terms in each case. b. c. m n , N“ C (a Mafia-fl Z3“ We??? CH3 0 CH3 t, W0 M} “\w»o/"' may o :- WK 4‘ ,1 " 7‘9 —' - /V«‘ ,r’n .1 _ _ J] z: M/ifiwzzé m»: a évwflfi v Wm {w «6? (‘ ‘ l h RZN 1 OH j. R—N:C:O C 0 #4 aw M Te? ’x , V Midi/$4 «am 1’? C349 * a” 2. Describe the most accurate relationship between the following pairs: OH O O a. t O b. .n 7 n and I C\ and I C\ _ HZN NH2 HZN NH r”) "I i ‘ ‘3. '1 Ff: "‘ \f g/ C 0' d. gHO H (IIHO and H—T OH O—T—H HO —-—|—H and H—I— OH H“— OH HO—-— H g ...,. r; . I f (£56: .. it CG CH0 CHO J' "V \J” 1* ~‘ x/ @512 at; 4“ €- 3‘6: t" Ware :1“ "‘ 93;“ a :7 mm — a: (I. ‘ HZN H HZN H HZN HZN H 1 ¥mfl7mwf 2 g 4 ~ ~ 7lm/oms ~ + g NHz NH h. NH2 NH2 N ,L and 2‘ | and bi N N Ell Iii H 0 g 0 H Milal/was MSG/7W0“ 5 6 7 g . C02H COZH . 1' H__ _OH H- ._0H J- PhNHCf = N-—Ph and PhNHENHPh H—— ——OH and H0— —H OH o CO H o H / 2 C 2 @mma 9/1; W3: 5‘ 1 EH3 + k. 1. m. H2NCHC02H and H3NCHC02— N\ and N N\ and N E .- OH {a a . / Myrizroé ~7a“ y/éfimdrr ervatyx ZM/iée’b 4 MC / an M25 3, The pKa values of cysteine (HSCHZCHCOZ—) are 1.7, 8.3 (the SH group) and m . | - at) #5 CHZCJJQJ/(f’) 605,94 NH3+ (15) 54:: H2 CHflJ/z’a) CO; 10.8. Write the predominant structure of this amino acid at pH values of a. pH : 1.0; b. pH : 12.0; c. pH 29.0; d. pH :3.0 i w . , 4‘ _ u :0 SCHZC#C~//3+ 302 Cd.) H555”2C*/{"/5’)C‘3z .Cl ltt H tth' 1t. 't(th PI) e acuae ep 21 CISOCCCI‘ICPOI‘Ié?‘ emfifi64) *Féh‘CéL/z n 5‘ O 4. In each of the following reactions indicate the type of reaction including symbol, where applicable. Examples: (a) CH3OK + CH31 => CH30CH3 : Nucleophilic alkyl substitution (8N2) (b) CH3OH + CH3COCI => CH3COZCH3 + HCI.Base : Nucleophylic Acyl Substitution base a. 3ONa + —-> - QChZOG-l3 b. Q—ONa + (302 ———-——> Q44}; 002 ‘Na 0. H2NCH(Cl-Q3)002H+ 02%;: ——-—> (Jaw—Q No2 Six/.2 r” x ’ ’ WWI-'42 M». 9‘“ 547 NHCH(CH3) 00241-1 N02 WWCPM e - xm $1,: ,1}; d. R1COZH +R—N=C=N—R ———> R_N=gNR I47”! y (Kr-5H A’ucgeg/Wfi‘éc’ {@fiffiffig R1 3% 0:: M M”? R2NH 3‘ 9— =97 ———i> RZNHC(O)R1+ R- 0Y0 R1 CH20H CHZOMe f 0 Et3N o . m H ‘AC205 0 Nb HO Meo OH OMe O Mezso4 2 6/142 6244"? H fa 926m 9. OH we ———> 0 Me NaOH “0 MeO OH 0M9 CHng CHZOH 0 x c‘dfix adv h. OH H HO 0020-13 H Br/ 0 H “*2 H2 OH 02 HO OH OH i. < +BrCHZCOZCHB __, firfimmr 7? m 52 \ ...,,. J «’7’- E L”) i: 3 4. A decapeptide (10 amino acid residues) having the'overall composition: Arg, Cys, Glu, Glyl, Leu, P [1, Tyr,’ Val upon hildroly'sis gives theiollowmg fragments: (32)» Val. gs. Gly + Gly. e. Phe + Glu. gig. Gly + Tyr. Leil. Val + G1y.,¢1u. Arg m. m. -'v/ A‘What is the original sequence of the decapeptide? Show how you arrive at your answer. -—--| ’ .11 ’7 f ’4’ /‘ / (1’71"! .‘ ,v 3 ‘7 3 _ _ r . , i , a Q/ 5‘ Mg‘ “$4 ‘ ‘ ‘ " fig ' é " to "3. “’ <9 @ (é 69 6/ 5. Give the predominant product including stereochemistry where appropriate. If no reaction occurs .write .“no rm” 0 i a. _ 1) H. NN. : “’1. , ' ’ 2) H30 :15 "x C‘ m b. H3N+CH2002+ Ph NCO _———» Pd “H % MK C42 02: > at; A; £19222?” 2" d. __‘___ ____..\ Z X Base ) 0/7. 44. \ v ; :1 —' + (echSS) -——-—-—-> K COLCf’i3 H2 c. CH30H=o + KCN + NH 401 co , 2 Cm; Caz/g 4 “3 CV2 e. + _ base ‘“ (t-BuOCO) 2.0+ H3N—?H—COZ ——————» #guO/g Awglw (:02 f. H —-NH(CH2)3——CH002— + NaOH ,, 2” fi NH2+ Amy (one equiv.) 4" M/z N {/2— EtON /EtOH < C o F 4 g- Q—CQQB, + CH acOZEt —*—a+—> .5>' 6' CHZ‘ ‘7' *" ((wa 0 gxcess _ / N uC‘ONHCfi (7'0, h. OzN—Q—F + H3+NCHCONHCH2COf 5 (3le H339 A in NO2 CH3 N03 . + 1) OH‘ ‘ / | 1' QNCS + H3NCHCONHCH2C02H ———-+—> 0 KC, chug? 1 2)H3O _, CH3 0 1' QCHfiCHCOEW <3/—CHZC‘H in; E NH3+ H3O . N l d , 4‘0 _; 9 1" QCHZOICIINHFHCONHCHZCOZPI—Ii» +42 M (i: ‘4 CC: Nu a... a; Co: L1 0 CH3 CH; _ 5 0‘. . \ <é>~ « . 04H ’0 N02+ f aid 2 / __.___* mononit ration product “it h : +W1 ‘4’!“ 4( n. CHSCHICOQH ’1)CI2,P mg (jut (was: My 2) NH 3 (excess) N U2 , + — m o H3NCHZCOZ +PhNCO .__—> ~ H 9' HchHOOZV+PhCH200CI3I ———> PACHZOCIENHfig Q01 NH3+ 0 obj}? 1NOH ,, . . q CHaCCHa + HO—22)—Z——-—> Q. (Hm-(Rica; 1! O 7. Given the structures of AA’s (HZNCHRCOOZH) as: Glycine (Gly), R:H; Phenylalanine,(Phe) R: PhCH2 and Leucine (Leu) R: isobutyl, write the structure of : a. Phe.Gly , b. GIy.Leu and c. Leu.GIy.Phe. How many tripeptides containing all three amino acids are possible? How many tripeptides are possible containing one or more of the above three AA’s‘? r +— + w “b H. NCH ~19” C Ca 0.) H3 N—CA/ CC? Ivy 0/3 Cafe k 2 :‘3 2g 1 a, fag/’5’ y (C ,3 8. Draw a graph of the surface tension of water as a function of surfactant concentration. Show the CMC on the plot. % 52 ac. \ )2 .5 I am \\\. i W" 6 "A “AM ' (,9 9. Write reaction mechanisms for: k H30+ + a_ RCNHR' -———> RCOZH + H3NR' /ffiit?& 3% \k ,7 0 N j \5 Pkg/MK?’ . @H\ ,p/W‘WR’ ’ \NHNQ' 10. Suggest the Merrifield synthesis of : 3- H3N +CH2 IC'? N HinNHCHZCOZ' from the corresponding amino acids using 0 CH3 0 P$~MCAQC€+ 90.20 CH2 NN- “79°C any. other needed reagents. J i "’ H Ow 4J4 .«-7> F5 -79), a2 05; C/(2N#»f/fiac W p5 .a 39/1.» 6/2 err/5: c722 ~69 WWW, 0 b i/A/Qgc (ii/{(59) WF.M:(‘ 62/3 MW) 9 we 54 6m «:3 ’ ~ 'I .. FWK 12v" W PS 4% CM; Qg CH2 1W4, (#13: a”? Haze: 0/3 WwFMac W4 N\_ / @2360sz r /'{,4.«¢~ New? W"\)u‘.‘P " C 3.} Mas b- CHZCHCO; using the Strecker synthesis. "h #c‘lv‘ w,» “ m “‘7 CAT .3 i " C C .. M MMMW My @c’fic”, ‘9 M43 “" \f> *’2 ” J Hm / “C #304— <:6>_<:H‘Z gun NHAM .2” 0‘ Synthesizel QCH=C(CH3)2 from CH3 and (CH3)2CO as the only carbon sources and any other needed reagent. ’ QC wV/ld and: 153/ 533 5:3: " “ r a 5 ' , *3: l > 1" ‘ r J“ ‘ “C " 5 . ‘IN m-w.~ mw‘wnd“ < 03> “1””: “a”? 53? *1 ‘5 “r {,1 Med; 55 :w “#3 M 7“ _ ~ch>n (24/3 ...
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322bs06_sample_final_key - cum WNW PRACTICE FINAL ' 006 1....

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