Chem 203 December 20, Final Exam Part II Problem 2 of 3 (30 points)
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1 Chem 203 December 20, 2014 Final Exam Part II Problem 2 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. 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 The following spectral data are provided for a compound with a molecular formula C 18 H 21 NO 4 : IR (KBr pellet), 500 MHz 1 H NMR, MHz 13 C NMR, DEPT-90, DEPT-135, COSY, TOCSY (60 ms mixing time), HMQC, HMBC, HSQC-TOCSY spectra with increasing mixing times (5, 10, 25, and 50 ms), and NOESY. 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.2.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 4.0 International License.
3 c. Tabulate the shifts of the 1 H resonances (a-q) 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: k: l: m: n: o: p: q: d. Redraw the structure of the molecule below and write the letter (a-q) 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 e. Tabulate the shifts of the 13 C resonances (1-18) 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: 11: 12: 13: 14: 15: 16: 17: 18: f. Redraw the structure of the molecule below and write the number (1-18) 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 4.0 International License.
5 Varian Resolutions Pro % Transmittance Wavenumber
6 1H spectrum Integral e k EXPNO 22 Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 5.7 DW usec DE 6.00 usec D sec MCREST sec MCWRK sec a,b c d f, g, h i,j l,m,n o p,q SFO MHz SI WDW EM LB 0.30 Hz PC 4.00 CHCl 3 1D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
7 DU=/v, USER=nmr14t, NAME=partII_C_h, EXPNO=22, PROCNO=1 F1=9.000, F2=0.000, MI=0.50cm, MAXI= cm, PC=4.000 # ADDRESS FREQUENCY INTENSITY [Hz] [PPM]
8
9 1H spectrum Integral CHCl 3 a b EXPNO 22 Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 5.7 DW usec DE 6.00 usec D sec MCREST sec MCWRK sec SFO MHz SI WDW EM LB 0.30 Hz PC D NMR plot parameters CX cm CY cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm
10 1H spectrum Integral k f g h i j l m n o p q EXPNO 22 Date_ Time PULPROG zg30 TD NS 64 DS 2 SWH Hz FIDRES Hz AQ sec RG 5.7 DW usec DE 6.00 usec D sec MCREST sec MCWRK sec SFO MHz SI WDW EM LB 0.30 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 , , , 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 DE 6.00 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 3.56 cm F1P F Hz F2P F Hz PPMCM /cm HZCM Hz/cm dept90 CHCl
12 EXPNO 5 gcosy60 2 Date_ Time PULPROG cosygp60.prd TD 2048 DS 16 FIDRES Hz AQ sec RG 5 DE 6.00 usec d sec D sec d sec IN sec 3 GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec 4 ND0 1 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined 5 SF MHz PC MC2 QF CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
13 EXPNO 5 gcosy Date_ Time PULPROG cosygp60.prd TD 2048 DS 16 FIDRES Hz AQ sec RG 5 DE 6.00 usec d sec D sec d sec IN sec 2.0 GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec 2.5 ND0 1 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined SF MHz PC MC2 QF 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 Date_ Time 0.03 PULPROG mlevgp_mo TD 2048 DS 16 FIDRES Hz AQ sec RG 16 DE 6.00 usec d sec D sec D sec d sec FACTOR1 4 IN sec l1 24 SCALEF 6 p usec P usec p usec P usec PL db GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec ND0 1 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined 5 SF MHz PC MC2 QF 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 gtocsy EXPNO Date_ Time 0.03 PULPROG mlevgp_mo TD 2048 DS 16 FIDRES Hz AQ sec RG 16 DE 6.00 usec d sec D sec D sec d sec FACTOR1 4 IN sec l1 24 SCALEF 6 p usec P usec p usec P usec PL db GPNAM1 sine.100 GPNAM2 sine.100 GPZ % GPZ % P usec 2.5 ND0 1 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined SF MHz PC MC2 QF 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 50 EXPNO 7 Date_ Time 1.21 PULPROG inv4gp.wu TD 2048 DS 16 FIDRES Hz AQ sec RG DE 6.50 usec CNST d sec D sec d sec d sec d sec d sec IN sec p usec ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec PCPD usec PL db PL db SFO MHz 100 GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 150 SF MHz WDW EM LB 7.00 Hz PC 1.40 MC2 QF SF MHz WDW QSINE SSB CX cm F2PLO F2LO Hz F2PHI F2HI 0.00 Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
17 ghmqc 30 EXPNO 7 Date_ Time 1.21 PULPROG inv4gp.wu TD 2048 DS 16 FIDRES Hz AQ sec RG DE 6.50 usec CNST d sec D sec d sec d sec d sec d sec IN sec 40 p usec ======== 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 ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 70 SF MHz WDW EM LB 7.00 Hz PC MC2 QF SF MHz WDW QSINE SSB 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 50 EXPNO 8 Date_ Time 2.45 PULPROG ghmbc.wu TD 4096 DS 16 FIDRES Hz AQ sec RG DE 6.00 usec CNST d sec D sec d sec D sec d sec IN sec p usec ======== 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 ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 150 SF MHz PC 4.00 MC2 QF SF MHz CX cm F2PLO F2LO Hz F2PHI F2HI 0.00 Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
19 ghmbc optimised for 10 Hz couplings 30 EXPNO 8 Date_ Time 2.45 PULPROG ghmbc.wu TD 4096 DS 16 FIDRES Hz AQ sec RG DE 6.00 usec CNST d sec D sec d sec D sec d sec IN sec 40 p usec ======== CHANNEL f2 ======== NUC2 13C P usec PL db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 70 SF MHz PC MC2 QF SF MHz CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
20 ghmbc optimised for 10 Hz couplings 25 EXPNO 8 Date_ Time 2.45 PULPROG ghmbc.wu TD 4096 DS 16 FIDRES Hz AQ sec RG DE 6.00 usec CNST d sec D sec d sec D sec d sec IN sec p usec ======== CHANNEL f2 ======== NUC2 13C P usec PL db SFO MHz GPNAM1 sine.100 GPNAM2 sine.100 GPNAM3 sine.100 GPX % GPY % GPZ % GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE undefined 40 SF MHz PC 4.00 MC2 QF SF MHz CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
21 HSQC-TOCSY (hsqcetgpml) 5 msec mixing time 40 EXPNO 24 Date_ Time 0.00 PULPROG hsqcetgpml TD 2048 DS 32 FIDRES Hz AQ sec RG 1024 DE 6.50 usec CNST d sec D sec d sec D sec d sec d sec d sec DELTA sec DELTA sec FACTOR1 0 IN sec l1 0 MCREST sec MCWRK sec SCALEF 6 ST1CNT p usec p usec P usec p usec P usec P usec PL db ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec p usec PCPD usec PL db PL db SFO MHz 80 GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE Echo-Antiecho 100 WDW EM LB 5.00 Hz PC 1.40 MC2 echo-antiecho SF MHz WDW QSINE SSB CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
22 HSQC-TOCSY (hsqcetgpml) 10 msec mixing time 40 EXPNO 25 Date_ Time 2.33 PULPROG hsqcetgpml TD 2048 DS 32 FIDRES Hz AQ sec RG 1024 DE 6.50 usec CNST d sec D sec d sec D sec d sec d sec d sec DELTA sec DELTA sec FACTOR1 0 IN sec l1 0 MCREST sec MCWRK sec SCALEF 6 ST1CNT p usec p usec P usec p usec P usec P usec PL db ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec p usec PCPD usec PL db PL db SFO MHz 80 GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE Echo-Antiecho 100 WDW EM LB 5.00 Hz PC 1.40 MC2 echo-antiecho SF MHz WDW QSINE SSB CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
23 HSQC-TOCSY (hsqcetgpml) 25 msec mixing time 40 EXPNO 26 Date_ Time 5.05 PULPROG hsqcetgpml TD 2048 DS 32 FIDRES Hz AQ sec RG 1024 DE 6.50 usec CNST d sec D sec d sec D sec d sec d sec d sec DELTA sec DELTA sec FACTOR1 1 IN sec l1 6 MCREST sec MCWRK sec SCALEF 6 ST1CNT p usec p usec P usec p usec P usec P usec PL db ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec p usec PCPD usec PL db PL db SFO MHz 80 GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE Echo-Antiecho 100 WDW EM LB 5.00 Hz PC 1.40 MC2 echo-antiecho SF MHz WDW QSINE SSB CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
24 HSQC-TOCSY (hsqcetgpml) 50 msec mixing time 40 EXPNO 27 Date_ Time 7.39 PULPROG hsqcetgpml TD 2048 DS 32 FIDRES Hz AQ sec RG 1024 DE 6.50 usec CNST d sec D sec d sec D sec d sec d sec d sec DELTA sec DELTA sec FACTOR1 3 IN sec l1 18 MCREST sec MCWRK sec SCALEF 6 ST1CNT p usec p usec P usec p usec P usec P usec PL db ======== CHANNEL f2 ======== CPDPRG2 garp NUC2 13C P usec p usec PCPD usec PL db PL db SFO MHz 80 GPNAM1 SINE.100 GPNAM2 SINE.100 GPZ % GPZ % P usec ND0 2 TD 512 SFO MHz FIDRES Hz SW FnMODE Echo-Antiecho 100 WDW EM LB 5.00 Hz PC 1.40 MC2 echo-antiecho SF MHz WDW QSINE SSB CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
25 noesy 2 3 EXPNO 23 Date_ Time PULPROG noesyrvtp TD 2048 DS 16 FIDRES Hz AQ sec RG 5 DE 6.00 usec D sec D sec D sec IN sec 4 ND0 2 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined WDW QSINE SSB 2 PC MC2 TPPI WDW QSINE SSB CX cm F2PLO F2LO Hz F2PHI F2HI Hz F1PLO F1LO Hz F1PHI F1HI Hz F2PPMCM /cm F2HZCM Hz/cm F1PPMCM /cm F1HZCM Hz/cm
26 noesy EXPNO 23 Date_ Time PULPROG noesyrvtp TD 2048 DS 16 FIDRES Hz AQ sec RG 5 DE 6.00 usec D sec D sec D sec IN sec ND0 2 TD 256 SFO MHz FIDRES Hz SW FnMODE undefined WDW QSINE SSB 2 PC MC2 TPPI WDW QSINE SSB 2 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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