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NMR (2009) Key - Chemistry 30B Sample NMR Problems Key 1...

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Chemistry 30B Sample NMR Problems Key 1) Label the indicated pairs of atoms or groups as Homotopic, Enantiotopic or Diastereotopic. 2) Draw the 1 H NMR and 13 C NMR for the following molecules. Note 1: The following numerical values are calculated so that you can see what the real values should be. However, you do not need this level of accuracy. Me Me O A O B OH OH OH Me Me OH Me Me H H OH OH H H H H C D E F Enantiotopic Diastereotopic Diastereotopic Enantiotopic Enantiotopic Enantiotopic O A 1 H NMR: 1.1 ppm (6H, d) 2.7 ppm (1H, septet) 1.8 ppm (1H, s (or t due to coupling thru alkyne to CH 2 )) 3.2 ppm (2H, s (or d due to coupling thru alkyne to CH)) 13 C NMR: 15 ppm (Me) 28 ppm (CH 2 ) 42 ppm (CH) 68 ppm (Alkyne CH) 80 ppm (Alkyne CH) 210 ppm (C=O) O NH 2 B 1 H NMR: 1.0 ppm (6H, d) 1.5 ppm (1H, multiplet) 2.0 ppm (2H, s, NH 2 ) 3.3 ppm (2H, d) 13 C NMR: 18 ppm (Me) 29 ppm (CH) 43 ppm (CH 2 N) 75 ppm (CH 2 O) 79 ppm (CH 2 O) 2.8 ppm (2H, t, CH 2 N) 3.6 ppm (2H, t)
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May see long range coupling ( 4 J) between the two meta aromatic protons.
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