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S06 final key - Organic Chemistry 30B Spring 2006 FINAL...

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Unformatted text preview: Organic Chemistry 30B Spring 2006 % FINAL EXAM, Page 1 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: P P‘ A i- r i- r H3C i-Pr Me 5 1H NMR: 06 2 mt: L '+ Z M 13c NMR: ___’X_ ___~:__ 2_ 4—! M b) (10 points) Name the following compounds by the IUPAC convention, unambiguously specifying any stereochemistry: O + 5 4 § OH (52-2 Z—adzue o5; eq/c‘a, z—Afidwxg— bfiflwm c) (6 points) Explain the following 1n just a few words at most, or with a Scheme. Define in the context of material seen this quarter: Why does a primary amine have two IR stretching frequencies (3350 and 3400 cm‘l) while a secondary amine only has one in the same region? i} —-/\):H /7 «Ar/7H 427/44. 94% $55311? H» N\H Mi Quflwawé I'd—H bow—«J Why 18 an ester less reactive to nucleophilesO than a ketone? air/3 /{C’?'/F— (~27 if; WW5?— Organic Chemistry 30B Spring 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 1): a) 3 _, 3 OH mm Al I U 31% UV! j/Mtk (32/ 4) |2 b) OH 0” 1)sto4 2) Ph3P=CH2 l +4 3) H2804, heat \U at“? K J) 2.) /7 —7 OH ; C) 002Me +4 1) KOH, H20 2) soc:2 / I I 3) Me CuLi \ 4) thAgBr V » A) d) 6 1) PhMgBr H0 C O 2) P00 —> Ph 3 Ph P=CH 43R0303H 2 7L 7 2 5) KCN l L {/7 Vi em, P7 LPh :27 )L/ph “7 fl/Ph Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 3 Name g 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 l): on a) Br .0 g: \pr’ \J b) Q 0&0 d) OH @- CHZCI 1) PPh3 2) BuLi 3) M9200 4) 0804, H202 1) KCN 2) LiAIH4 3) ACZO 1) EtOH, heat 2) SOCI2 —————> 3) Ph2CuLi 4) NaBH4 1) PBr3 2) M9 —> 3) :0: Ph 4) H2304, heat I \ / O + é COO 56‘ . ”b x. (or o Organic Chemistry 303 Spring 2006 % FINAL EXAM, Page 4 y/ Name 4. (25 points) Provide a step-by-step mechanism for the following reaction (no shortcuts!). Make sure to show all intermediates and byproducts in addition to the correct arrow—pushing formalism): O a) (10 oints) (Z p \JWflr-sev COOMe 2 eq MeMgBr OH (H30+ workup) /\ 9,... / ““3 ea ‘ o 29 S' 9 b) (15 points) . ‘ H ’ 03H m , . H90 0 v K7 MeO OMe MeOH M ‘ $0 9 6 cat. H2804 is He? (K3641 wk g H “\ (9 / + 1 H Organic Chemistry 303 Spring 2006 K ‘ FINAL EXAM, Page 5 Name 5. (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 303). There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. 0"“ —>—» CH5 U“ i a) (8 points) n? b) (12 points) 0H (”(610.4 g), Organic Chemistry 30B Spring 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: 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. a) (10 points) Hsc _,. C; Cl b) (10 points) Organic Chemistry 30B Spring 2006 K FINAL EXAM, Page 7 N ame 7. (25 points) a) @oints) Sketch the 1H NMR spectrum for the compound below. Be sure to consider chemica ifts, coupling patterns, and relative intensities between each spin system when drawing your spectrum. Label H’s on the structure (a,b,c, etc) and the corresponding peaks: 1o 9 8 7 6 5 4 3 2 1 0 (ppm) b) (10 points) A compound with molecular formula C4H603 has the IR spectrum below. Its 1H NMR has a unique signal at 2.15 ppm. Provide structure and assign IR-absorption bands: Degree of unsaturation: i 4 ( Structure: ‘0 O (glee/7c, .. [I\ DA : (fig-3i: Z / O/K m%‘£fl% 4’3 we nmtrmzuu 3 ChemNMR 1H Estimation 0.96 H30 2.35 Estimation quality: blue = good, magenta = medium, red = rough 1 O 8 6 4 2 PPM Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 8 Name 8. (35 points) A compound has the molecular formula C9H304. 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: Degree of Unsaturation: é (mm —$_ é ED Z, bl Compound C9H804 IR spectrum (film): (assign a minimum of 5 absorptions) <4, 2’ ML [00 I'lflNSHll'l'flNtEIkl 0| 9 "00 1H NMR spectrum. Assign specifically what peak is what part of the structure in addition to labeling integrations and (by letters or arrows; show also structure on this page): O 10 HQOC 13C NMR Spectrum. Assign the 13C signals to positions on the structure, except for those purely aliphatic or aromatic; show on this page: D :J 20 6040 $1! 0 // \ '; 1H 6 C 10 1 £0 1L 9 2H 2‘; 70 ...
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