Experiment 34 Discussion - Experiment 34 Discussion: NMR...

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Experiment 34 Discussion: NMR data: The H NMR of the product has 5 unique signals. The first 4 signals are 2 coupled hydrogen sets. They are the signals from the two benzylic and allylic Hs. The second and fourth deshielded signals are the allylic Hs, with the more deshielded corresponding to the hydrogen closer to Br. The first and third signals are the two equivalent benzylic signal Hs, with the more deshielded hydrogen closer to the alylic substituent. The large peak with an integration value of 3 corresponds to the methoxy hydrogens. The 2 nd and 4 th Hs exhibit coupling constant values of 13.9. This is useful in determining the structure of the compound. Trans coupling is expected to be between 12-18, so this value tells us the Hs are oriented trans to each other, thus Br and the phenyl group are also located trans. In the C NMR there are 7 unique signals. The most deshielded is the alkene C closest to Br. The next is the benzylic C with the methoxy substituent. The next 4 signals are the remaining benzylic carbons, and the other alkene carbon. The most
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This note was uploaded on 02/21/2011 for the course CHEM 3b taught by Professor Pederson during the Fall '08 term at University of California, Berkeley.

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Experiment 34 Discussion - Experiment 34 Discussion: NMR...

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