Chem 203 December 20, Final Exam Part II Problem 1 of 3 (30 points)
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1 Name: Chem 203 December 20, 2014 Final Exam Part II Problem 1 of 3 (30 points) 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. 1 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.
2 The following spectral data are provided for a compound with a molecular formula C 10 H 17 NO 2 : IR (thin film from CHCl 3 on salt plates), 500 MHz 1 H NMR, MHz 13 C NMR, DEPT-90, DEPT-135, COSY, HMQC, HMBC, TOCSY (100 ms mixing time), NOESY and a 1D NOE experiment. All NMR spectra were measured in CDCl 3 solution. 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. MAKE SURE TO COMPLETELY ANSWER THE QUESTIONS a-f ON PAGES 2-4. a. Write the structure of the molecule. If there are any aspects of your structure that don't seem to make sense, please feel free to comment on them below: b. Build an energy-minimized molecular model of the molecule using PyMOL and the "clean" function. Use the side menu (S) to show each molecule as sticks (Show-sticks). Use the pulldown menu to display each molecule in maximum quality with (Display-Quality-Maximum Quality). Save the.pse files as Problem_II.1.pse. the.pse files to me (jsnowick@uci.edu). Alternatively, you may build an energy-minimized model of the correct diastereomer using Maestro/MacroModel with the MMFF force field. me (jsnowick@uci.edu) the -out.maegz file associated with that model. 2 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.
3 c. 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: d. 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 International License.
4 e. 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: f. 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. 4 This work by Dr. James S. Nowick, Professor of Chemistry, University of California, Irvine, is licensed under a Creative Commons Attribution International License.
5 Varian Resolutions Pro % Transmittance X H 2 O Wavenumber
6 1H spectrum Integral h i j EXPNO 1 Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 3.2 DW usec D sec MCREST sec MCWRK sec SFO MHz SI WDW EM LB 0.30 Hz PC 0 a b c d e f g 1D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm CHCl
7 DU=/v, USER=nmr14t, NAME= Act II A, EXPNO=1, PROCNO=1 F1=9.000, F2=0.000, MI=0.50cm, MAXI= cm, PC=00 # ADDRESS FREQUENCY INTENSITY [Hz] [PPM]
8 1H spectrum Integral a b c EXPNO 1 Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 3.2 DW usec D sec MCREST sec MCWRK sec SFO MHz SI WDW EM LB 0.30 Hz PC 0 1D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
9 1H spectrum Integral f EXPNO 1 d e g Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 3.2 DW usec D sec MCREST sec MCWRK sec SFO MHz SI WDW EM LB 0.30 Hz PC 0 1D NMR plot parameters CX cm CY cm F1P F Hz F2P 00 F Hz PPMCM /cm HZCM Hz/cm
10 1H spectrum Integral h EXPNO 1 i j Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 3.2 DW usec D sec MCREST sec MCWRK sec SFO MHz SI WDW EM LB 0.30 Hz PC 0 1D NMR plot parameters CX cm CY cm F1P 00 F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
11 Z-restored spin-echo 13C spectrum with 1H decoupling C{1H} dept CDCl 3 CHCl EXPNO 2 Date_ Time PULPROG SpinEchopg30gp.prd TD NS 1024 DS 16 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 PL1-0 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 0 Hz PC 0 1D NMR plot parameters CX cm CY 3.56 cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm dept90 CHCl
12 Z-restored spin-echo 13C spectrum with 1H decoupling 13C{1H} dept EXPNO 2 Date_ Time PULPROG SpinEchopg30gp.prd TD NS 1024 DS 16 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 PL1-0 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 0 Hz PC 0 1D NMR plot parameters CX cm CY 3.56 cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm dept
13 EXPNO 5 gcosy60 Date_ Time 0.30 PULPROG cosygp60.prd TD 2048 NS 4 DS 16 SWH Hz FIDRES Hz AQ sec RG 5 DW usec d sec D sec d sec IN sec SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec F1 - Acquisition parameters ND0 1 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined 3.0 SI 2048 WDW SINE PC F1 - Processing parameters SI 1024 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 EXPNO 6 Date_ Time 0.52 PULPROG mlevgp_mo TD 2048 NS 8 DS 16 SWH Hz FIDRES Hz AQ sec RG 5 DW usec d sec D sec D sec d sec FACTOR1 7 IN sec l1 42 SCALEF 6 p usec P usec p usec P usec PL db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec F1 - Acquisition parameters ND0 1 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined 3.0 SI 2048 SF MHz WDW SINE PC F1 - Processing parameters SI 1024 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
15 ghmqc 25 EXPNO 7 Date_ Time 2.12 PULPROG inv4gp.wu TD 2048 NS 8 DS 16 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 50 p usec SFO MHz ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec PCPD usec PL2-0 db PL db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ3 20 % P usec F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined SI 2048 WDW QSINE PC 1.40 F1 - Processing parameters SI 1024 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
16 ghmqc EXPNO 7 Date_ Time 2.12 PULPROG inv4gp.wu TD 2048 NS 8 DS 16 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 20 p usec SFO MHz ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec PCPD usec PL2-0 db PL db SFO MHz 25 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ3 20 % P usec 30 F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined SI 2048 WDW QSINE PC F1 - Processing parameters SI 1024 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
17 ghmbc optimised for 10 Hz couplings 25 EXPNO 8 Date_ Time 3.37 PULPROG ghmbc.wu TD 4096 NS 8 DS 16 SWH Hz FIDRES Hz AQ sec RG DW usec CNST d sec D sec d sec D sec d sec IN sec 50 p usec SFO MHz ======== CHANNEL f2 ======== NUC2 13C P usec PL2-0 db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec 125 F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined SI 2048 WDW SINE PC F1 - Processing parameters SI 1024 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
18 ghmbc optimised for 10 Hz couplings 20 NAME partii_a EXPNO 8 Date_ Time 3.37 PULPROG ghmbc.wu TD 4096 NS 8 DS 16 SWH Hz FIDRES Hz AQ sec RG DW usec CNST d sec D sec d sec D sec d sec IN sec p usec SFO MHz ======== CHANNEL f2 ======== NUC2 13C P usec PL2-0 db SFO MHz 25 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec F1 - Acquisition parameters ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 30 SI 2048 WDW SINE PC 1.40 F1 - Processing parameters SI 1024 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 EXPNO 9 gnoesy Date_ Time 5.36 PULPROG noesygptp TD 2048 NS 8 DS 16 SWH Hz FIDRES Hz AQ sec RG 5 DW usec D sec D sec D sec d sec IN sec 2 P usec SFO MHz 4 GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec F1 - Acquisition parameters ND0 2 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined 6 SI 2048 WDW QSINE SSB 2 PC 1.40 F1 - Processing parameters SI 1024 MC2 TPPI WDW QSINE SSB D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI 0.00 Hz F1PLO F1LO Hz F1PHI F1HI 0.00 Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
20 EXPNO 9 gnoesy Date_ Time 5.36 PULPROG noesygptp TD 2048 NS 8 DS 16 SWH Hz FIDRES Hz AQ sec RG 5 DW usec D sec D sec D sec d sec IN sec P usec SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec F1 - Acquisition parameters ND0 2 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined 3.0 SI 2048 WDW QSINE SSB 2 PC F1 - Processing parameters SI 1024 MC2 TPPI WDW QSINE SSB D NMR plot parameters CX cm CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO 2159 Hz F1PHI F1HI 347 Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
21 gnoe NAME partii_a_noe EXPNO 3 Date_ Time PULPROG gnoe1cc.wu TD NS 256 DS 8 SWH Hz FIDRES Hz AQ sec RG DW usec D sec D sec d sec d sec p usec p3 20 usec p usec p usec P usec SFO MHz SP db SPNAM1 gauss12 SPOFF Hz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPNAM4 sine.100 GPX % GPX % GPY % GPY % GPZ % GPZ % GPZ % GPZ % P usec SI SF MHz WDW EM LB 0 Hz PC 0 1D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
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