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322bf03_final_key

322bf03_final_key - Fall 2003 Organic Chemistry 322bL...

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Unformatted text preview: Fall 2003 Organic Chemistry 322bL Monday, December 15, 2003 G \/ aifi Final Exam Name Initial of Last Name l::‘ T.A.’s Name ‘ 1. ________ (30 pts) 2.______—____________ (10 pts) (10 pts) 4.___________—___ (10 pts) 5._______—______ (30 pts) 6._________—_____ (10 pts) 7.—___________— (10 pts) 8.____________________— (20 pts) 9._______~____— (15 pts) 10.____________— (20 pts) 11.—_____ (15 pts) 12._________________ (10 pts) 13.____________________________— (10 pts) Total _______(200 pts) gflc/V 1. Write the products of ten/9f the following eleven reactions. (30 pts.) E e W ENHN Et3N a. Ph-CHz-O-C-CI + H3N-CH2-C~NH-f3H- -——> TH2 mete—E M» Uki'M‘Wi © 9m 01 _ _ f? 9 b. Ph-N-C—S + H2N-(i2H-C-NH-fiiH-C-NH-(EH-C-OEt S 0 H2 CH3 0 ' “ , M (S 063 I\CHQ, E‘NH’E‘NA’EM‘MM C'M OHe A in (M3 pH9 W ‘ S c. A—3——>H 06‘ Pk~N)‘\W‘( A cmk H d. OZN—QF + HzN-(iiH-E—NH-(fH-E—NH-fH-E—NHN ————> N02 THz CH3 sz G CS 1) HCO? NaQ/HZO "KH 2) aq. HCI 0‘ l W. Med-04“ 0L (1% W o I h. @(OH + CH3-$H CH HP 9 ‘ o - 2- -C_O —> . 0” CH3 EH? I . Q E 1? fi’ HBr M iv I. CH2-O- -NH-1:H-C-NH-?H—C~NVV‘ WRW +602.) CH3 $H2 .v R . - r1 M-{M— www- /CK ‘ CH3 CH3. V MMOIC 1) CH CHNH /pH5 ', k. <3=o ~ch—% 2) NaBH3CN In no more than 15 words explain, why the N-C bond labelled C is longer than the N-C bond labelled B? You may find that resonance structures can be efficiently utilized in your explanation. (10 pts.) ‘1 [TH CM” CM HgN—C—NH W M Arginine H NH2 H 5 lysine i figu Mm ,C‘L—N“, H sc‘NW’N L u U' 4. The following compound was recently detected in arterial plaque. This was taken as evidence for the presence of what oxidant? Write the structure of the substrate which is oxidized to yield this product. Name it. (10 pts.) I; ’1’ HO 5_ Give an illustrative example of the use of each reagent. (30 pts.) LiAIH (0+)3 NaNOz/ HCI ©NW’ "" 63 / ~ 0 a 0 9,9» m a) (1)PhSeCi/ (2) H202 " '——- d; H Phag—SH2 . 80/4 d a? PROV—fa if CH3 6. Qc—céup CHZ‘C H 3 Write the product of this reaction. Write a kinetic rate expression for this reaction. Write the structure of the starting material after half of it has reacted. (10 pts. (on. = r: mum (9 C \i / ‘ K c *C‘K‘ V’aCévm 4 SSC‘MAC\ in WV) ‘ m'xKgcheq (a ‘/ LT HQ “wtfim Z: {I \ do. H lb 7. Convert 1,3-cyclohexfiionb \to 95 given any organic and/or « O ‘0 inorganic reagents you need. (TO 8. Tyrosine has been converted to thyroxine, an amino acid hormone produced in the thyroid gland which regulates metabolism, by the following sequence of reactions. In each step, in which no reagent or reagents are specified, you are to write the reagent needed to achieve the transformation. (20 pts.) 02 “H2 HN03 u H I HOW lCozH HOCOZH H (1) 02N 0 q i? 2 NH-C-CH3 1) (CH3—C) O Hob/i, 2 2) EtOH/H’a ’COzEt O2N H 8-0 Q 1(2) org—@‘B ‘lgfb No R Q“? 2 NH-C-CH3 (lit, 02 Toso—W’koza WCHso'Q—Ob/i N OZN H 02 (4) O'HW d!le CH3 :0 W NH2 NH (5) CHso‘Q CH30©'O-©/\1 ’COQEt l H NH2 (6) H: I NHZ l Tos —-§— (‘6 N QCHB 0 H2 H0 I'COZH Thyroxine I I H 9. The pKa of acetic acid is 4.76, while the pr of methyl amine is 3.36. Explain why the pKa H l CH2- -COZH of tryptophan is 9.4 and its pr is 2.4. I NH2 N H In a few words, why is tryptophan not considered a basic amino acid? (15 pts.) M. g p «3 “haw i W: p n A; 45 CC)? 1o. \ hydrazine. Y-ose and X-ose are 9/62! mas - . Ruff degradation of Y-ose yields an aldotetroses Z-ose ,(Noxidation with HNO3 yields an optically inactive Z- aric acid. Ruff degradaton : yields D-glyceraldehyde. Oxidation of Y-ose with HN03 yields optically activcid. On the other hand, similar reactions of X-ose with HN03 yields optically inactive X-aric acid. Aldopentose Y-ose forms the same oxazone as X-ose , on reijtion with excess phenyl Write the structures of Y—ose,_X-ose, and Z—ose. Use chemical equations to show your reasoning. (20 pts.) 001M ESL! Bow. Z’QVTL l l/wl H We, f—J SW 0H 0", B — com 5W \I “W19 (L0 4)! COZH 12. HO OH Cholic Acid, an important component of hu ' n bile, is pud in the liver and stored in the gall bladder. Select the correct _ ' of Cholic Acid. Label the circled substituents of the correct structure =- as equatorial as appropriate. (10 pts.) o 3H 0 3‘6”: H O Wifd: QE'CHs Cw QUE-CH3 cHa 601 R Q?“ QOH + CH3-C-CH3 CH3 “ 3 o l CHz'CHz , CHz-C-H was) Given the following oxidizing agents, choose which one is selective for each of the transformations. Write the reagent chosen above the arrow. Answer five out of the six fmuestions ( Opts.) (—4 ‘41)on — e KMnO4, MnOz, H20r04, <\ INH Cro3cf? E e e ozone, CF3 -OOH, 02, 0‘04/ fiv-o, HCIO, HC|O4 :‘ 40:)” Cl ...
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