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In an effort to identify it, an unknown compound, U, was subjected to extensive

ID: 597401 • Letter: I

Question

In an effort to identify it, an unknown compound, U, was subjected to extensive spectroscopic analysis. In addition, the mass spectrum of compound U was aquired. A molecular ion peak was observed at m/z = 166, and the molecular formula for compound U was thereby determined to be C9H10O3. A peak at m/z = 121 was by far the most intense peak in the mass spectrum. Determine the structure of compound U. Be sure to include a concise discussion of the reasoning. Construct tables summarizing the IR and 1H NMR data, and assign the peaks in the IR and NMR spectra to the appropriate structural elements in U. Explain the appearance of the base peak at m/z = 121 in the mass spectrum. The first figure shows the IR spectrum for compound U and the second shows the 1H NMR spectrum.

In an effort to identify it, an unknown compound, U, was subjected to extensive spectroscopic analysis. In addition, the mass spectrum of compound U was aquired. A molecular ion peak was observed at m/z = 166, and the molecular formula for compound U was thereby determined to be C9H10O3. A peak at m/z = 121 was by far the most intense peak in the mass spectrum. Determine the structure of compound U. Be sure to include a concise discussion of the reasoning. Construct tables summarizing the IR and 1H NMR data, and assign the peaks in the IR and NMR spectra to the appropriate structural elements in U. Explain the appearance of the base peak at m/z = 121 in the mass spectrum. The first figure shows the IR spectrum for compound U and the second shows the 1H NMR spectrum.

Explanation / Answer

What is the integration of the three peaks around 2.2-2.5? Are all three singlets? In the carbon NMR, the three peaks at 77 ppm are due to CDCl3 - you can disregard them.

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