Chem 203 December 10, Final Exam Part II Problem 3 of 3 (30 points)
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1 Chem 203 December 10, 2011 Final Exam Part II Problem 3 of 3 (30 points) Name: Select and submit TWO OUT OF THE THREE PROBLEMS FROM PART II for grading. Do not submit three problems. If you wish to unstaple the pages, please initial each page. Books, notes, lecture videos, calculators, rulers, and laptop computers are permitted as is wireless (or wired) internet access and appropriate software (e.g, Pymol, Macromodel/Maestro, Excel, NMRPrediction, Chemdraw, ElComp, MolE, etc.). Catalogs of molecular structures (e.g., the Aldrich catalog, the Merck Index, etc.) or databases of molecular structures (such as wireless access to SciFinder Scholar, the Sigma- Aldrich website, etc.) are NOT PERMITTED. USE OF SUCH ITEMS CONSTITUTES ACADEMIC DISHNONESTY, WILL RESULT IN A FAILING GRADE (F) IN THE CLASS, AND MAY RESULT IN EXPULSION FROM THE Ph.D. PROGRAM. If you wish to use a laptop computer, please be willing to share briefly with others when needed. 1 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
2 2. The following spectral data are provided for a compound with a molecular formula C 10 H 16 O: IR (Thin Film on NaCl), 500 MHz 1 H NMR, MHz 13 C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY, and NOESY. Using these data, determine the structure of the compound and assign all of the 1 H and 13 C resonances to their respective atoms in the structure. Make sure to determine the stereochemistry of the compound and to clearly assign 1 H resonances to the appropriate diastereotopic protons. All NMR spectra were measured in CDCl 3. The 1 H resonance at 7.27 corresponds to CHCl 3. MAKE SURE TO COMPLETELY ANSWER THE QUESTIONS a-f ON PAGES 2-4. a. Write the structure of the molecule. 2 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
3 b. Tabulate the shifts of the 1 H resonances (a-j) in order of descending chemical shift. Provide an appropriate name for each multiplet (e.g., s, d, t, q, quintet, sextet, septet, octet, dd, ddd, dt, td, dddd, tt, qd, dq, etc.) and list its coupling constants in appropriate order; also list its integral [e.g., a: 3.30 (t, J = 7.3 Hz, 3 H)]. If a resonance is not described by a well-defined multiplet, name it as m and give its range [e.g., c: (m, 2 H)]. a: b: c: d: e: f: g: h: i: j: c. Redraw the structure of the molecule below and write the letter (a-j) of each 1 H resonance next to the proton or protons to which it corresponds. If the assignment of a particular resonance is uncertain, please indicate this. 3 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
4 d. Tabulate the shifts of the 13 C resonances (1-10) in order of descending chemical shift. Make sure to report the chemical shift of each carbon resonances to the nearest tenth of, unless two have the same value, in which case you may report it to the nearest hundredth. 1: 2: 3: 4: 5: 6: 7: 8: 9: 10: e. Redraw the structure of the molecule below and write the number (1-10) of each 13 C resonance next to the carbon or carbons to which it corresponds. If the assignment of particular resonance is uncertain, please indicate this. f. Build an energy-minimized molecular model of the molecule using PyMOL and the "clean" function. Save the.pse file as problem3.pse. the.pse file to me (jsnowick@uci.edu). If you have encountered any problems of which I should be aware in grading this problem, please let me know, below. 4 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution 4.0 International License.
5 Thin Film on NaCl plates
6 1H spectrum at 500 Mhz in CDCl3 Integral NAME sample 18 EXPNO 99 Date_ Time PULPROG zg30 TD NS 8 DS 2 SWH Hz FIDRES Hz AQ sec RG 4 DW usec D sec MCREST sec MCWRK sec NUC1 1H P usec PL db SFO MHz SI SF MHz WDW no PC D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
7 DU=/v, USER=nmr11t, NAME=sample 18, EXPNO=1, PROCNO=1 F1=4.000, F2=-0.500, MI=0.50cm, MAXI= cm, PC=4.000 # ADDRESS FREQUENCY INTENSITY [Hz] [PPM]
8 1H spectrum at 500 MHz in CDCl3 Integral e g h NAME sample 18 EXPNO 99 Date_ Time PULPROG zg30 TD NS 8 DS 2 SWH Hz FIDRES Hz AQ sec RG 4 DW usec D sec MCREST sec MCWRK sec NUC1 1H P usec PL db SFO MHz c SI SF MHz WDW no PC 4.00 a b d f i j 1D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
9 Z-restored spin-echo 13C spectrum with 1H decoupling at 125 MHz in CDCl NAME sample 17 EXPNO 2 Date_ Time PULPROG SpinEchopg30gp.prd TD NS 108 SWH Hz FIDRES Hz AQ sec RG DW usec D sec d sec d sec MCREST sec MCWRK sec P usec NUC1 13C P usec P usec P usec PL db PL db SFO MHz SP db SP db SPNAM1 Crp60,0.5,20.1 SPNAM2 Crp60comp.4 SPOFF Hz SPOFF Hz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db SFO MHz GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % p usec p usec SI SF MHz WDW EM LB 1.00 Hz PC D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
10 Z-restored spin-echo 13C spectrum with 1H decoupling at 125 MHz in CDCl NAME sample 17 EXPNO 2 Date_ Time PULPROG SpinEchopg30gp.prd TD NS 108 SWH Hz FIDRES Hz AQ sec RG DW usec D sec d sec d sec MCREST sec MCWRK sec P usec NUC1 13C P usec P usec P usec PL db PL db SFO MHz SP db SP db SPNAM1 Crp60,0.5,20.1 SPNAM2 Crp60comp.4 SPOFF Hz SPOFF Hz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db SFO MHz GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % p usec p usec SI SF MHz WDW EM LB 1.00 Hz PC D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
11 Z-restored spin-echo 13C spectrum with 1H decoupling at 125 MHz in CDCl NAME sample 17 EXPNO 2 13C{1H} Date_ Time PULPROG SpinEchopg30gp.prd TD NS 108 SWH Hz FIDRES Hz AQ sec RG DW usec D sec d sec d sec MCREST sec MCWRK sec P usec dept135 NUC1 13C P usec P usec P usec PL db PL db SFO MHz SP db SP db SPNAM1 Crp60,0.5,20.1 SPNAM2 Crp60comp.4 SPOFF Hz SPOFF Hz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db SFO MHz GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % p usec p usec SI SF MHz WDW EM LB 1.00 Hz PC D NMR plot parameters CX cm CY 3.56 cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm dept90 X X X
12 Z-restored spin-echo 13C spectrum with 1H decoupling at 125 MHz in CDCl NAME sample 17 EXPNO 2 13C{1H} Date_ Time PULPROG SpinEchopg30gp.prd TD NS 108 SWH Hz FIDRES Hz AQ sec RG DW usec D sec d sec d sec MCREST sec MCWRK sec P usec dept135 NUC1 13C P usec P usec P usec PL db PL db SFO MHz SP db SP db SPNAM1 Crp60,0.5,20.1 SPNAM2 Crp60comp.4 SPOFF Hz SPOFF Hz ======== CHANNEL f2 ======== CPDPRG2 waltz16 NUC2 1H PCPD usec PL db PL db SFO MHz GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % p usec p usec SI SF MHz WDW EM LB 1.00 Hz PC 2.00 dept90 X X X X X 1D NMR plot parameters CX cm CY 3.56 cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
13 NAME sample 18 EXPNO 5 gcosy60 0 Date_ Time PULPROG cosygp60.prd TD 2048 NS 4 SWH Hz FIDRES Hz AQ sec RG 35.9 DW usec d sec D sec d sec IN sec NUC1 1H P usec PL db SFO MHz 1 GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec F1 - Acquisition parameters ND0 1 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 2 WDW SINE PC 2.00 F1 - Processing parameters MC2 QF WDW SINE D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
14 gtocsy NAME sample 18 EXPNO 6 0 Date_ Time PULPROG mlevgp_mo TD 2048 NS 4 SWH Hz FIDRES Hz AQ sec RG 4 DW usec d sec D sec D sec d sec FACTOR1 4 IN sec l1 24 SCALEF 6 1 NUC1 1H P usec p usec P usec p usec P usec PL db PL db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec 2 F1 - Acquisition parameters ND0 1 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined WDW SINE PC F1 - Processing parameters MC2 QF WDW SINE 2D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
15 ghmqc 20 NAME sample 17 EXPNO 7 Date_ Time PULPROG inv4gp.wu TD 2048 NS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec CNST d sec D sec d sec d sec d sec d sec IN sec NUC1 1H P usec p usec PL db SFO MHz 30 ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec PCPD usec PL db PL db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec 40 F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined WDW EM LB 5.00 Hz PC F1 - Processing parameters MC2 QF SF MHz WDW QSINE SSB 3 2D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
16 ghmqc 17 NAME sample 17 EXPNO 7 Date_ Time PULPROG inv4gp.wu TD 2048 NS 4 SWH Hz FIDRES Hz AQ sec RG DW usec DE 6.50 usec CNST d sec D sec d sec d sec d sec d sec IN sec NUC1 1H P usec p usec PL db SFO MHz 18 ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec PCPD usec PL db PL db SFO MHz 19 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec 20 F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined WDW EM LB 5.00 Hz PC F1 - Processing parameters MC2 QF SF MHz WDW QSINE SSB D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
17 ghmbc optimised for 10 Hz couplings NAME sample 17 EXPNO 8 Date_ Time 0.06 PULPROG ghmbc.wu TD 4096 NS 4 SWH Hz FIDRES Hz AQ sec RG DW usec CNST d sec D sec d sec D sec d sec IN sec 50 NUC1 1H P usec p usec PL db SFO MHz ======== CHANNEL f2 ======== NUC2 13C P usec PL db SFO MHz 100 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec 150 F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined SI 2048 WDW SINE PC F1 - Processing parameters MC2 QF SF MHz WDW SINE 2D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
18 ghmbc optimised for 10 Hz couplings 20 NAME sample 17 EXPNO 8 Date_ Time 0.06 PULPROG ghmbc.wu TD 4096 NS 4 SWH Hz FIDRES Hz AQ sec RG DW usec CNST d sec D sec d sec D sec d sec IN sec NUC1 1H P usec p usec PL db SFO MHz 25 ======== CHANNEL f2 ======== NUC2 13C P usec PL db SFO MHz 30 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec 35 F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 40 SI 2048 WDW SINE PC F1 - Processing parameters MC2 QF SF MHz WDW SINE D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
19 NAME sample 18 EXPNO 24 gnoesy 0.5 Date_ Time PULPROG noesygptp TD 2048 NS 4 SWH Hz FIDRES Hz AQ sec RG 57 DW usec D sec D sec D sec d sec IN sec NUC1 1H P usec P usec PL db SFO MHz 1.0 GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec 1.5 F1 - Acquisition parameters ND0 2 TD 422 SFO MHz FIDRES Hz SW FnMODE undefined 2.0 WDW QSINE SSB 2 PC F1 - Processing parameters MC2 TPPI WDW QSINE SSB 2 2D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
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