30B_Fall06_Final Exam_AK - Organic Chemistry 30B Spring...

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Unformatted text preview: Organic Chemistry 30B Spring 2006 k FINAL EXAM, Page 1 , W Name 1. (20 points) a) (6 points) Give the number of expected signals (ignore splittings) in the 1H and 13C NMR spectra of the following compounds: ’I WHWI’ OHH I C“; as \“ O “b t W "I? O i O k ,4. t-BUO%\Ot-Bu How“M o H""0H 3 w; "BUD ( 1H NMR: g 13C NMR: Z { g b) (8 points) Name the following compounds by the IUPAC convention, unambiguously specifying any stereochemistry: ( o i I L 3 I I“, Z 3, ,(fmeffaé- I, 3 r y-W-5—pzn (CW " Z’OQQ/ 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: Illustrate with an example the following: Phosphorus ylide \Gp ch-v? \P C j P z, , “1 Why is an amide much less reactive to nucleophiles than a ketone? flab/22d 5 Momma 0 Q0 C {3. <9 Organic Chemistry 30B Spring 2006 K ‘ FINAL EXAM, Page 2 3/ i Name 2. (30 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) - (Br jicm pBra / EtONa I 9003“ ——» A —-> EtOH,H+ OH PCC CH0 PhsP=CH-002Et , —> A —-> 056 age at? Wm mmmmmmmmmmmmmmmmmmmmm WWW—“WNW ~ - “W5 ) b) 0" 002Et (99K 6062 \(/ NaOH, H20 ( soc: MeMgB' ————> C j -—>2 : —>‘““’ Fin H+, heat —> 0) EtONa Organic Chemistry 303 Spring 2006 g , k HNALEXAM,Ege3 ( :7 Name 3. (30 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) 0 0H phMgBr EtMgBr H+, H20 \ CN -———> ——-———> ——-—-> V (then H30+) % \ PL @H C (D W 0 ” o. HIo4 H /l\ 9H. m —’ Pit ’k/ Pa V (+ CHSCHD) b) PBr3 Mg Cu! @ LOX 6 ’1 H2304 I?“ Ph (no heating) “3 . + ; Fin \‘ c) O 0 XS. LiAIH4 CHI/ah (Egg) C cno [fton Cf/o O l PB E ON ; F4. (2 age.) 7“ (2t eqj i (66:5 P‘L Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 4 Name 4. (20 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) (10 points) 0 .- /~, ., n ( W C 9 g (-1 62 H0 ff. H #4 H2021 H" H b) (10 points) CD {a n? Itst ° CR/ MeMgBr (H30+ workup) J 7 r H '0‘!" @ H Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 5 Name 5 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 I 0 steps necessary in these syntheses, although longer ones may also be correct. a) (6 points) Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 6 W 3/ 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. WW _’——* (l (/fggce/ o 0 e730 W078; z? /\ '90" L Mfg/tut #00 or a) (10 points) Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 7 Name 7. (20 points) a) (10 points) Sketch the 1H NMR spectrum for the compound below. Be sure to consider chemical shifts, 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: 10 9 (ppm) b) (10 points) Provide a structure of the compound with molecular formula C4H4O3 that has the following 13C NMR spectrum: 0 / Degree of unsaturation: 2 Structure: (¢XZ)4L"‘/ 1701— Z :3 \ (ech/uu'dc/e/c cw) Organic Chemistry 30B Spring 2006 FINAL EXAM, Page 8 M Name /' 8. (40 points) A compound has the molecular formula C14H19NO. 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: 6 (/¢xz)-Iz ~/? +/ Z IR spectrum (film): (assign a minimum of 4 absorptions) 100 SD TRINSHITTIMCEI 2| 3001! 200i 15nd 1000 500 WENUHI ER! -|l 1H NMR: Draw structure here as well and label all non-symmetrically related H’s on the structure (e.g. with a,b,c, etc). Show which peak the labels correspond to on the spectrum by drawing arrows to them. Provide labels for integration values (1H, 2H, 3H) and peak multiplicities (splitting type): 13C NMR spectrum for question 8. Draw the structure here again and assign the 13C signals to specific carbons on the structure. However, aliphatic carbons or the alkene/aromatic peaks do not need to be assigned specifically for each carbon (just label them as a general range of peaks): MFA ~ 20 O l © 1 ...
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