322bs04_final_key

322bs04_final_key - s ' 2004 \ / IL Ofglggic Chemi§tw...

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Unformatted text preview: s ' 2004 \ / IL Ofglggic Chemi§tw 322bL K) M CL /M % , 5} 965 yzl/Té lnitialof Last Name E Name T.A.’s Name 1-____________ (60 pts) 2-__._._______..—_— (10 pts) 3-_.___________——— (18 pts) 4'_____._..__._____—— (10 pts) 5-______._._.__———— (15 pts) 6'____._______————— (10 pts) 7-__________.__.-._.._ (10 pts) 8'_________——————- (10 pts) 9'______._.__.————— (10 pts) 10-_..__..______..___._ (20 pts) 11-_____;__________ (5 pts) 12-________________ (5 pts) 13.______'_________ (5 pts) 14-______________.__._ (20 pts) Tota|______________ ( z, a Y) - 1. Write the products of the following reactions. (60 pts.) "'————5 hfi «)1 mm / COZCH3 COthg 1% {‘CLLW/ C Q + [COZCHS m CM [-2 large excess 0 m f. (j + CH30H L 040% 35ml} 3’ / 9 [Cox k. 9 CW6- CM,— Gym-‘04 CH3—fiDH-C—NH—fi2H—COZH H2 , Pd gong M T“ it: ’ w: 0 A =0 / \ Chm—E 65 we? N i? E ||-I , O CH2—o—C—NH—gH-C—0Et 5 H2 ’2; chwcoé’c lmlt W4 1 Evy m. (CH3)3C-0E-NH-$:—E-OH M» 7: + COWfi-M 0H @ Q 3% 9 9 OHO 8“ ON=C=S + H2N-QH—C-NH-QH-CW—pfi‘é" A QM’G-MM n. E E O O 0&0” ‘9 R ——» P- + H3N—gH—C—O O N 1 out: M21 0 ,0 9 wt “' W Coz CW 0‘ q. CH3—C-HN-gH—COZH w, (a \ 62 éwzd. %m@ w @ Racemic )4 ' r M [OM 041606711441 I‘M SC 144,0 #4)}? { coo/6) ’ OCHZ—E—H PM“ 9”” m/ I 3 M Maw; «W (K \, ‘ e e e 9 0nd“? (9 $02 (9 $03 s. H3N—cfH—Co2 ———> H3N—(IDH H3-N-(I3H $1.12 CHz—S-S—CHs SH Cysteine Specify the type of reagent you need to convert cysteine to the disulfide cystint? t‘ HO 6% fi-OOH o 61% (-c/‘(M 2. Name fl\_/.e_of the compound below. Select from the list of names below. (10 ptsT' a: V CH3 CH2) H co H \ __ a; 2 H H \\ mm NIL-QM‘ V‘ D?" _ NW H5 H 5H Lauric acid Stickalotic acid Oleic Acid Estradiol Limonene Testosterone Prostaglandin E2 ,0 7L / 6/ \ Squalene Cortisone Progesterone r05 43 a M l ‘4 E7; Cholesterol Vitamine 02 Progestipol 5 leach, 3. Give an illustrative example of the use of each of the following reagent. (18 pts.) 0 a. LiAlH (0+)3 Qr—arq ,____. W b. LiBH3CN Go +MLN/V -—v O/ml/V O c \ l If (MW e.» a-“ ®H e. HIo4 clam/(Mt 2 C :0 M5 All W1 f. H2(1 atm) Pd on BaCOswith quinoline Omafi-icqclg .._.a \5/ 0 g. Ph3P=CH2 4- a ,9 Q; 0 63 o h. Ph-SeBr é ___. é/S‘m" w» b {£17343}! i. 01/ —> Ht“&wloH® A Specify a reagent to accomplish this reaction. m,%h [H F, L 0L tWoKJmk R3h67 M} 4. If you nitrate an equal molar mixture of benzene C(SH6 and 06D6 with HNO3 and concentrated sulfuric, what is the ratio of the products CBHSNO2 and CeDsNO2 you will obtain? What does this demonstrate about the - of this aromatic electrophilic substitution (nitration) reaction? (1 0 pts. W M COQH 5. Given toluene prepare isomericallly pure m-nitrobenzoic acid Q Convert this efficently into meta-hydroxybenzoic acid. N02 (15 pts.) 6' 0H“ MW “w’owf Write the energy levels of the n—molecular orbitals of the cyclopentadienide anion. In two sentences at most, account for ease of proton removal from 1,3-cyclopentadiene. (10 pts.) 7. Azulene is a blue colored hydrocarbon which has a permanent dipole moment. C in a few sentences account for these observations. Draw the dipole. Be certain to show its direction. (10 pts.) ‘96-) 8. 2CH3Li T (CH3)ZCULi Give two examples of reactions which can be accomplished with a dialkyl cuprate which would lead to failure or a different result with the corresponding alkyl lithium reagent. (10 pts.) 0 «Zebu «rail/lb) O 9. Draw the n-molecular orbitals of 1,3-butadiene. Arrange them in order of increasing energy. Label these bonding (B), non-bonding (N), or anti-bonding (A). Label the lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO). In no more than three sentences account for the bond length 1.47A° of the 02-03 bond in 1,3-butadiene. (10 pts.) 10. Bradykinin (a potent pain causing agent) is a nanopeptide released by blood plasma globulins in response to a wasp sting. Complete hydrolysis followed by amino acid analysis yields the following composition:A@7_fily, Phez, Pros, and Ser. Treatment of Bradykinin with 2,4-dinitrofluorobenzene followed by hydrolysis yields: 6) o $02 “70—” . . NO: 2)3 N ’W M N02 [2 While treatment of Bradykinin with carboxypeptidase gives: These two facts give you what information about the structure of Bradykinin? Partial hydrolysis of Bradykinin followed by sequencing the di- and tripeptides give the following information: PheSer, ProGlyPhe, ProPro, SerProPhe, PheArg and ArgPro. Write the amino acid sequence of Bradykinin. (20 pts.) 1 We Wm PM. 3"” SW Plehrfi W0 we, 10 11. Circle the isoprene units in Vitamin A. (5 pts.) @& 12. Circle the more acidic OH group of estradiol. (5 pts.) 13. Circle the more basic nitrogen atom in nicotine. (5 pts.) \ “SPF—«ww H N/ CH3 11 lo 14. Given Ph-CHg-O-E-NH-CHg-COgH , t? EtO-C-Cl , H3N-CHQ-C-NH-fH-C-NH—CfH-CO2H “E CH(CH3)2 CHZ-Ph n r-NH- H-CO H :3 -2 CH(CH3)2 Specify the chemical reactions used to remove the protecting groups. (20 pts.) PL’CVL; (it o D-C 'NWWJCDM * 3 €01 DCC MjC—H Met—Wo— Marga 12 i? cvMHLCMz \ (LSD ...
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This note was uploaded on 10/12/2009 for the course CHEM 322B at USC.

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322bs04_final_key - s ' 2004 \ / IL Ofglggic Chemi§tw...

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