{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

W08 final key - Organic Chemistry 30B Winter 2008 6 FINAL...

Info icon This preview shows pages 1–11. Sign up to view the full content.

View Full Document Right Arrow Icon
Image of page 1

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 2
Image of page 3

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 4
Image of page 5

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 6
Image of page 7

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 8
Image of page 9

Info icon This preview has intentionally blurred sections. Sign up to view the full version.

View Full Document Right Arrow Icon
Image of page 10
Image of page 11
This is the end of the preview. Sign up to access the rest of the document.

Unformatted text preview: Organic Chemistry 30B Winter 2008 6;}, FINAL EXAM, Page 1 me 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: >LP/k & i \T T/ 1HNMR: '7" i Q 9/ (/ { OQ~ 13CNMR: _(_ _/_Z/_ i— “F l 0‘" b) (8 points) Illustrate the following absorption patterns in a proton NNR spectrum: Sextet Doublet of triplets c) (6 points) Illustrate the following with an example: 1; ’8/ Diazomethane 4/ 1 Cuprate (9 Qt, t; , . t -~ ,, [genre-m awful/”w ( 072 “2) [229a “(a Amides are difficult to hydrolyze, even in aqueous acid. Show why with a brief illustration 7 U , r’z/ G9 a) \Q l, 4;": /‘rL/‘ \x fl , £1 6Q Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 2 2. (30 points) Draw the major product as well as intermediates for each step (for max. credit) for the following reactions (if there are enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed!) Aqueous workup (e.g. H3O+) is implied after each step where needed: 1)PhMgBr 2) P00 W, O 3) CH2=CH-Li <2 4: ——-> i ‘1; 4) SOCI2 f ‘7 5) KCN, DMF V 6)MeMgBr, then H30+ 4;) 1) CH2=N+=N‘ 2) MeMgBr (2 eq) COZH 3) HBr ——-———-> 4) KOt-Bu 5) RCO3H b /\ W. 6) EtZCuLi m 0”“ ”W (a? ’04 \em ’4 4 l J 1) RCOSH 2) PhLi . 3) H2804, heat ( -. l —————> d 4) 0504, H202 ‘ fl 7 ) then NaHSO3 \ \l W 5) H|O4 ~. ’37 '/\ J) ”gaff/b! Um 1*? kafl Q31 d) Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 3 3. (30 points) Draw the major product for the following reactions (if there are enantiomers or diastereomers formed, show only one, but pay attention to stereochemistry where needed!) Aqueous workup (e.g. H3O+) is implied after each step where needed: Br 1) Mg, THF 2332.344 \\ \/\ COOP] 3‘ 4) HBr - ~~ 5) KCN DMF L y M i 6) H30+, heat H U A @Afll 3"? 0A6 O 1) NaBH4 O H ' 2) PBrs 2-“ 83 3) EtONa . 4) R003H \i‘ '0. 5) MeSNa ‘ 6) RCOSH M (1 eq.) /’ H 9H 1) SOCI2, pyridine .4 2) KI 1 ..i/ —-——-————-——> 3) KCN 4) LiAIH4 (l. 5) acetone, H+ \_, m I CN d) i \/ 0 ’12 1) 0304 then H202 2) H+ ———-————-———-> L. 3)NaBH4 4) NaH, Mel Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 4 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) V/\ Wm“ Meow H+ . m V WM L 2’ «LE/w Q \, (9 , \ 0 9/ H b) (10 points) H o 0 OH CH2N2 OMB 500 (17 ~ (:9 C. H : N 7N / x Z" k/ / \«2 ‘3 v 6: Cm/wiv Organic Chemistry 30B Winter 2008 . FINAL EXAM, Page 5 , ’ me 5. (25 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 308). There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. : ,COOH a) (10 points) / ~- “Mf/ i (Qsz U / /”/ CO ’ WV /\/,C(1ZCH l l I \ / l l / _\—5 l COOH Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 6 6. (25 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 303). There should not be more than 10 steps necessary in these syntheses, although longer ones may also be correct. a) (10 points) imply“ ”016% b) (15 points) ChemNMR 1H Estimation 099 0.99 1.40 O 3.83 6.97 7.51 OH 4.38 \ 215 3.50 O NH 10.01 6.97 7.51 Estimation quality is indicated by color: good, medium, rough 10 8 6 4 ‘ 2 Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 7 Na 7. (20 points) a) (12 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. Draw arrows from the structure to the corresponding peaks: 1o 9 8 7 6 5 4 3 2 1 0 (ppm) b) (8 points) Provide a structure of the compound with molecular formula C3H403 that has the following 13C NMR spectrum. There is only one line in the 1H NMR: #7 0 Degree of unsaturation: " Structure: /H\ (3! Z) ~+ z V Cr" +3 0 O {3% :- ._—-—:—~ 2 1 \,_/ V +5 160 ’ 140 120 100 : 8‘0 60 40 2h 0 PPM Organic Chemistry 30B Winter 2008 FINAL EXAM, Page 8 8. (30 points) A compound has the molecular formula C7H7NO. Deduce its structure from the IR, 1H NMR, and 13C NMR spectra given below. You MUST provide all the relevant information (including peak assignments) to get maximum credit. Draw the structure in the box provided: t? Degree of Unsaturation: { (” «elk-7, “7 4’” l / P a?“ 1 IR spec rurfi ilm): (assig 3 type of stretching absorptions) 100 rlmsmrrmnzu a O “M 3000 200! 13M 10M “0 1H NMR: Draw the structure here also, and draw arrows from all non—symmetrically related H’s on the structure to the corresponding peaks in the spectrum. Provide labels for multiplicities (splitting type): o ~N y _ + «m g7 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): 0 160 140 120 100 80 60 4o 20 PPM 180 ...
View Full Document

{[ snackBarMessage ]}

What students are saying

  • Left Quote Icon

    As a current student on this bumpy collegiate pathway, I stumbled upon Course Hero, where I can find study resources for nearly all my courses, get online help from tutors 24/7, and even share my old projects, papers, and lecture notes with other students.

    Student Picture

    Kiran Temple University Fox School of Business ‘17, Course Hero Intern

  • Left Quote Icon

    I cannot even describe how much Course Hero helped me this summer. It’s truly become something I can always rely on and help me. In the end, I was not only able to survive summer classes, but I was able to thrive thanks to Course Hero.

    Student Picture

    Dana University of Pennsylvania ‘17, Course Hero Intern

  • Left Quote Icon

    The ability to access any university’s resources through Course Hero proved invaluable in my case. I was behind on Tulane coursework and actually used UCLA’s materials to help me move forward and get everything together on time.

    Student Picture

    Jill Tulane University ‘16, Course Hero Intern