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classes_Fall09_30BID17_A2Key

classes_Fall09_30BID17_A2Key - 2 Use your knowledge of 1 H...

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Chem 30B Week 2 Worksheet NMR Spectroscopy 1. For the following compound and its associated spectrum a. Label the “upfield” and “downfield” ends of the spectrum b. Determine which signal corresponds to which hydrogen c. Which resonance is at higher energy? d. Which set of protons has greater shielding? e. In the solid state, this molecule has 4 proton signals while only 2 are visible in solution. Explain. 0 1 2 3 PPM e. In solution, there is bond rotation around all σ -bonds so all equivalent protons show up at the same chemical shift. In the solid, this rotation is no longer possible so protons near the carbonyl oxygen will experience a different environment to those farther from the oxygen, thus, more resonances. Upfield Downfield Higher energy Less shielding Lower energy More shielding
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Unformatted text preview: 2. Use your knowledge of 1 H NMR Spectroscopy to assign each of the following structural isomers to its correct spectrum. Assign all signals to their corresponding hydrogens. 2H 6H 2H 2H 1H 3H 3H 2H 2H 1H O O O O O H O 3. Use your knowledge of 1 H NMR Spectroscopy to assign each of the following compounds to its correct spectrum. Assign all signals to their corresponding hydrogens. t, 4H t, 4H s, 2H t, 6H q, 4H s, 1H q, 4H t, 6H OH HO N H O 4. Label the highlighted protons as homotopic, enantiotopic, or disastereotopic. 5. Use the following spectra to write the structural formula for C 8 H 9 NO 2 . Make sure to label all pertinent peaks. d, 2H d, 2H s, 1H s, 1H s, 3H enantio homo Diastereo Diastereo homo HO H N O HO H N O HO H N O N-H O-H C=O...
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