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CHM3217 Practice Exam 3 - CHM 3217 Organic Biochemistry I...

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Unformatted text preview: CHM 3217 Organic Biochemistry I EXAM 3 Fall 2008 Print Name Total Points = 105 (4 points each, 40 points total) Predict the product or products. Indicate stereochemistry where required. You may use the symbolism (i) to indicate a racemic mixture of enantiomers. If no reaction occurs, write “NR.” 1. 1. LiA1H4 / Et20 2. H3OEB 2. 0 CH3NH2 a ——> 3. CH3 POC13 / pyridine 0H " 0°C 4. OH K2CI'207 —-—-—————>— H20 / HOAc, heat 5. O SnClz / H20 ———-——-—I-— O 6. Br: 2 CH3SH —> 7. O /\/H\ 1. DIBAIH, Toluene ——-—-—-—-—-—)~ 0 0/\ -78 C 2. H309 8. O HOCH2CH20H _'—"' H 6 cat 9. 0 $9 (Ph)3PCHCH3 ———-—-ar THF 10. MN NaOH / H20 Room Temp 11. (10 points) Using the Williamson ether synthesis, design a method to make the molecule below using the appropriate starting materials: O\/\ 12. (10 points) Starting With l-methylcyclohexene, synthesize the following molecule using the appropriate reagents. (3W 13. (10 points) Starting with styrene (phenylethylene) synthesize the following molecule using the appropriate reagents. COZH 14. (15 points) Write a mechanism for the following reaction: M 1 NHon / cat H30. ¢N 2. 30012 15. (10 points) Write a mechanism for the following reaction: 0 O NaOH COZH _... + CO2 H20 16. (10 points) An unknown compound gives a mass spectrum with a weak molecular ion at m/z 1 13. There is also a prominent ion at m/z 68, an a—cleavage fiagment. Its [R and NMR spectra are shown below. You may use scrap paper to work through the problem, but this will not be collected. Below the spectra, clearly and neatly Show your proposed structure. wavelengthmm) ' 25 3 3.5 4 45 5 6 7 8 9 10 11 12 13 141515 _ . 5.5 100 ' ' a wmammals"r"-memesmagmas.Easement-innings ‘ l‘l‘llllilllllh'illlllllllllllllllllllllllll‘lfilflllfllfllfi ““HillllllllllilIllllllfilllllll‘ulllllllllfllllllllllllflfifllflfl‘lflfl “ill!" I .I‘Ilflfllflflflll lllfllll lllfllilllllilflflfllflflfl llllllll Hllll'llllflll l[III IillllllllllfllHlllflllll‘llili I Illlyili'llllilllIIIHEEI‘IIIEEIE“ ' I. a" sameness? " Bllllli‘i'llmlll'lnln“'. ""'lll"l%u"lil""tl“ll‘l'.lmash-u “‘1'- ll lllilllllla“:l'"llll'lllllllll::llul InstallI:'1:Ellifilial!allalllli':lllillHl0:I'::Hs::1l"-'!:'EEE‘EEE““"|IE Illilllilllllllll lllHllll ElIlllIlFllEll|I[llIlllilllllillililil]Illlllilllllfllll I Illllllllllllllill IIIIIIli‘ilfllllll’fllfllllllflliflll IIIIIIIEIIEHEIE Ell' llll "llllllllll"" {Elli llllllllllllllfilllllllll lillllllllllfilllllilfllllllllllllllfilllllll ' 'llllllllllll‘l Ell ‘llllllllll lllallflllllllfllililll " flllllllll fill" 'lllllllll‘é'ullu llllllll Hill llllfilllllll lllllglfll Elli}! llllh lllllllllllllllflllilllllllh 'lllllllliii'ulfllllllllli': 20 El? llllllll‘lllfllfllllflllllllllllllllllIlllllllllllllllllllllllllllllllllln lllllfillllllllll llllllllllllfllfllhfififilfilfiiflfifliflflflflflfl Ellllllll l: fillill' EllfillfllllllllllllillllllllllllHillllllllllllllll {ll ulllllllllllllllllllllllillll Illlllll"um“llllllllllllllllIillfllllllflllllfli Ell' Illlllllllllll lfillllllllllllllll ll “lllllllllll'” ’lllllfilllllllfillllllfllllflfllll ill I llllllllllll ’“lllll lllllllllllllllllflllfilflllllllll 0 2500 2000 fiboa 1691c; 1400 1200 1000 300 am ...
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