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322bs06_sample_final_blank - Ming 2006 PRACTICE FINAL 1...

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Unformatted text preview: Ming 2006 PRACTICE FINAL 1. Circle and name the functional groups. Use the most specific terms in each case. a. —B OC—NHCH c. ”u 3 b- Owfl n O / \ CH3 CH3 0 d /—\ e. f /—\ 0 (43:0 NH o N Y 0 Pl 0 g. 18 h, RzN i. Oj j. R—N:C=O Lo 2. Describe the most accurate relationship between the following pairs: 0 O OH a. O b. H u and /C\ and /C\_ H2N NH2 H2N NH O. 6 o d. 9H0 910 (a (I H—rOH HOTH HO—-|—H and H——|—on H—QH HO———H I CIIHO CHO H 2“ I ‘) and k I ‘) 2* I ‘) and k I ‘) N N N N N N N N HZN H HZN H HZN H HZN H 1 2 3 4 + g NH2 NH h NH2 NHZ N It I N‘) and ILI I \> N | and I\I I ‘N N N N )N — N I | H O H O H H H 5 6 7 8 . co2 COZH . " H__ —OH H_ --0H J- PhNHc|3=N——Ph and PhNHfiNHPh H— —OH and H0— —H OH o COZH 02H CH3 I + _ k. 1. m. HZNCHCOZH and H3NCHC02 N and N N and N I O H 0 3 OH 3_ The pKa values of cysteine (HSCHZCIHCOQ— ) are 1.7, 8.3 (the SH group) and NH3+ 10.8. Write the predominant structure of this amino acid at pH values of a. pH = 1.0; b. pH = 12.0; C. pH = 9.0; (1. pH 2 3.0 e. Calculate the pH at the isoelectric point (the PI). 4. In each of the following reactions indicate the type of reaction including symbol, where applicable. Examples: (a) CH3OK + CH3I => CH3OCH3: Nucleophilic alkyl substitution (5N2) (b) CH3OH + CH3COC1 :> CH3C02CH3 + HCl.Base : Nucleophylic Acyl Substitution base a. CH 30Na + Q‘Chza ———> QChzOG'ls b_ QM + 002 __. Q22. 002Na c. H2NCH(CHB)COZH+ OZN—QF —> OzN—Q—NHCH(CH3)CID2H N02 N02 N-R d. R1COQH +R-N=C=N-R —> R_N=c R1 CHQOH CHQOlVe f o Et3N o . ——> 6” OH AC2O 0 Me HO MeO OH OMe CHZOH CHQOMe O M62804 0 9' OH Me ——+ o OMe NaOH HO MeO OH OMe CHZOH CHZOH 0 Br /HO 2 2 h' OH OH OOH COQH H0 002 i< ‘N_<:> +BrCHzCOZCH3—> 1. 045(0st L Q +N<CH3>3 4. A decapeptide (10 amino acid residues) having the overall composition: Arg, Cys, Glu, Glyz, Leu, Phez, Tyr, Val upon hydrolysis gives the following fragments: Val. Cys. Gly + Gly. Phe. Phe + Glu. Arg. Gly + Tyr. Leu. Val + Gly. Glu. Arg What is the original sequence of the decapeptide? Show how you arrive at your answer. 5. Give the predominent product including stereochemistry where appropriate. If no reaction occurs write “no rxn” O a‘ 1 ) H 2NNH2 | N: K + BrCH2C02C2H5—> ————>2)H3O+,A b_ H3N+CHZC02+ Ph NCO ——> C. CHsCH=O + KCN + NH 4C| d. Base :1 — +CH3| (excess) ——-> + _ base (t'BUOCO) 20 + HBN—(I:H_002 ———-‘> CH3 f. H2N—CID—NH(CH2)3——CHCOQ— + NaOH —-—> EtONa/EtOH (2 equiv.) excess h. + _ _ OZN‘Q’F + H3NCHCONHCH2CO2 ’ CH3 No2 i + 1)0H' ‘ NCS + H3NFHCONHCH2C02H —-———> 2) H o+ CH3 3 1 LA J-CHO— CHco'2 —————>) 1 ”:4 2 H 0 NH; ) 3 Hz/Pd HONHC HCFHCONHCHzcozH—» o I. \ + CMC ——»~02 / m. —— m + 0w ——» n. 1 Cl ,P CH30HaCOZH —)—2——> 2) NH 3 (excess) 0 @CHQonEH + PhCH2OCOCI ——> mononit rat ion product NH3+ 1 NaOH p. CHSCCH3 + @—cHo —)————> ll 2) A 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 2 a. Phe.Gly , b. Gly.Leu and c. Leu.Gly.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? 8. Draw a graph of the surface tension of water as a function of surfactant concentration. Show the CMC on the plot. 9. Write reaction mechanisms for: H 0+ 3 » RCQH + HJNR' a_ RENHR O b. HOC NHR H30“ H00 > OH + Rwy HO OH OH OH 0. NHC=N—<:> + R'NH2—> RENHRw O'NHCNH H O NH2 Cl d. {/ij +2NH3——> (“tfjN +NH4CI R/N N R/N N 10. Suggest the Merrifield synthesis of: a. H3N+CH2 C NHCHCNHCHZCOz' from the corresponding amino acids using II || 0 CH3 0 any other needed reagents. b. @CHfijHCOE using the Streckersynthesis. NH3+ 0‘ Synthesize: O—CHzC(CH3)2 from @—CH3 and (CH3)2CO as the only carbon sources and any other needed reagent. ...
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