W06 final key - Organic Chemistry 30B Winter 2006 FINAL...

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Unformatted text preview: Organic Chemistry 30B Winter 2006 FINAL EXAM, Page 1 V , Name 1. (25 points) a) (9 points) Give the number of expected signals (ignore splittings) in the 1H and 13C NMR spectra of the following compounds: Cl H HOWOH "3 L \N/ CH; H36 ’4 0K} H Y” 3: N CH3 2, 3 ‘f (“a“) 13C NMR: 1 __ —j___ l— (i. [61%) 1H NMR: b) (10 points) Name the following compounds by the IUPAC convention, unambiguously specifying any stereochemistry: H0 c) (6 points) Explain the following (in just a few words at most, or with a Scheme!) Define in the context of material seen this quarter: Why is the amide IR stretching tgquency (1650 cm") lower than a typical ketone (1715 cm‘l): f 0/6953 M W N \ . Why is an aldehyde more stable than its hydrate? : 9 O «9 H70 0 '1 T j /u\ 657 J ————9 H . H \ w 6—— O H Organic Chemistry 30B Winter 2006 FINAL EXAM, Page 2 Name % 2. (25 points) Draw the major product for the following reactions (if there are several enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed l): a) 1) RCO3H 2) KCN -———> 3) KOH, then H30+ 4) CH2N2 b) 1) H2NNH2, KOH, heat 2) R003H -—-—> 3) MeOH, H+ 4) P00 W d) :: CHZOH 1) BH3 2) H202, KOH 3) CTO3, H2804 4) P205 L) mini/id.» 1) TBSCI, Et3N 2) MeMgBr —-——-—-——> 3) CHZO 4) P00 5) MeMgBr 6) BU4N+F_, H20 Organic Chemistry 30B Winter 2006 ' » FINAL EXAM, Page 3 Name 3. (25 points) Draw the major product for the following reactions (if there are several enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed !): a) B 1) KCN u) N C0051? r A/ 2) H2804, heat 4* 6 3) EtOH, H+ b) 1 soc: COO” 2; EtNH: NH E’f 3) LiAIH4 UL J C) 1 KOH, H o P“ C023 3) PhZCuLi ' 4) MeMgBr H Cfl O k + 7 d) NH 1) LiAIH4 + g 2) acetone, H+ Organic Chemistry 30B Winter 2006 FINAL EXAM, Page 4 Name 4. (25 points) Provide a step-by-step mechanism for the following reaction (no shortcutsl). Make sure to show all intermediates and byproducts in addition to the correct arrow-pushing formalism): a) (18 points) i o (a >0 Z {5 > 3 Organic Chemistry 30B Winter 2006 k FINAL EXAM, Page 5 r, ' Name 5. (15 points) Provide a step-by-step mechanism for the following reaction (no shortcutsl). Make sure to show all intermediates and byproducts in addition to the correct arrow-pushing formalism): a) (9 points) +4 H @/ H . “P :0 ‘U at" H OH H30+ b) (6 points) NaBH4, MeOH —' 3H3 /\CHO then H30+ workup /\CH20H R7 H V! \ / I4 Q G 5., Organic Chemistry 30B Winter 2006 FINAL EXAM, Page 6 Name 6. (20 points) Devise a reasonable synthesis for the following compound from readily available reagents and the starting material provided (pay attention to stereochemistryl): Note: do no “invent” new reagents or reactions. Use only those specifically taught in class (30A or 30B). There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. a) (10 points) o /CooH goal ‘ Cece 5564 / g“ > { , ”’9 \ if b) (10 points) / MOWW Organic Chemistry 303 Winter 2006 FINAL EXAM, Page 7 Name 7. (20 points) Devise a reasonable synthesis for the following compound from readily available reagents and the starting material provided: Note: do no “invent” new reagents or reactions. Use only those specifically taught in class (30A or 308). There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. Br I —> © 00 (only source of aromatic rings) /\ H251»? l a) (‘ points) 5’ (1r7l\ ~——-—""7 {\ /[ / _/ \ l 2’ b) (3 points) Br Organic Chemistry 30B Winter 2006 k FINAL EXAM, Page 8 ‘ Name 8. (20 points) a) (10 points) Sketch the broadband decoupled 13C NMR spectrum for the compound below: OCHO 1o 9 8 7 6 5 4 3 2 1 0 (ppm) b) (10 points) A compound with molecular formula C4H7N has the IR spectrum below. Its 1H NMR has two signals at 1.35 (d) and 2.72 (sept) ppm. Provide structure and assign IR—absorption bands: 2’ Structure: C?“ Degree of unsaturation: , ($421+: «Vii-I CW?” ‘T : L (M) 71%? nmumuxu 8 Organic Chemistry 30B Winter 2006 FINAL EXAM, Page 9 WWI? Name 9. (25 points) A compound has the molecular formula C10H2203. Deduce its structure from the IR, 1H NMR, and 13C NMR spectra given below. You MUST provide all the relevant information (peak assignments) to get maximum credit. Draw the structure in the box provided: 0 Degree of Unsaturation: @XZ’)+ Z ’22 compound C10H2203 IR spectrum (film): (assign three absorptions) 100 nmsmrrmczm 8 4800 3000 m “It! 1000 I” 1H NMR spectrum. Please assign 1H NMR signals to specific positions of the structure (by letters or '\ arrows; show structure on this page): V‘; ° § n8 4. N 4. N $ N 4. \o —:— ’1 H1 13C NMR Spectrum. Please also assign the 13C signals to carbons of the structure, except for those purely aliphatic or aromatic; show on this page: O Q '\ 1} e; \ o \ N m C 0 ¢ \ “‘ 2 O. D. 80 100 ...
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