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You are given an impure sample of a phenol and asked to purify it. You ask for information about the suspected impurities, but it seems no one really knows. So you ask for an IR/NMR spectra of the impure sample. Upon scrutinizing the IR spectrum carefully, you find that there is a small, but significant, signal at about 1700 cm-1, a small broad peak at about 3000 cm-1 and a much stronger broad peak centered at about 3580 cm-1. That gives you an idea about the nature of the impurity, so you scrutinize the 13C NMR spectrum, looking for a short signal at ~170 ppm- you find it. You then look for a signal in the 10-13 ppm range in the 1H NMR spectrum- there seems to be a little “blip†on the baseline at 11.5 ppm, but it is not very clear.What can you say about the nature of the impurities, based on the IR spectrum? How does the 13C NMR signal at 170 ppm support this conclusion? What were you looking for in the 10-13 ppm range in the 1H NMR spectrum? Explain your reasoning.

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