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Problem of the Day #04 – Answer Key This problem is worth a total of 20 raw points. Each part is worth 10 points . In each part below, a 1 H NMR spectrum is shown. Beneath each spectrum, four structures are given. Circle the structure of the compound that produced the NMR spectrum. You will earn 6 points for circling the correct structure. To earn the remaining 4 points for each part, explain briefly how you arrived at your answer (use the back of the page if you need more space). (a) O OH OH O Explanation : The fact that a 1 H signal disappears upon shaking with D 2 O immediately excludes the ethers, since only protons attached directly to oxygen or nitrogen undergo chemical exchange in this way. The 6H doublet suggests the presence of 2 equivalent methyl groups (total of 6 hydrogens) adjacent to a CH group (the 1 neighboring proton causes splitting of the signal into 2 lines according to the n+1 rule). Only the circled structure is consistent with this data! (b)
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This note was uploaded on 10/25/2010 for the course CH 310n taught by Professor Iverson during the Summer '08 term at University of Texas at Austin.
- Summer '08