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1 and 950 ppm what is its structure how would you

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Unformatted text preview: ormation is mildly interesting but is essentially negative—it tells us what is not there but gives us no information on the basic skeleton, where the carboxylic acids are, nor does it reveal the 1,2- diketone in the middle ring. Solutions for Chapter 3 – Determining Organic Structures The mass spectrum would at least give the molecular formula C14H6N2O8 and the infra- red would reveal an N–H group, carboxylic acids, and perhaps the 1,2- diketone. The X- ray was utterly convincing and the molecule has now been synthesised, confirming the structure. O H only two C–H bonds HO2C N one N–H bond N H HO2C CO2H H PROBLEM 4 The solvent formerly used in some correcting fluids is a single compound C2H3Cl3, having 13C NMR peaks at 45.1 and 95.0 ppm. What is its structure? How would you confirm it spectroscopically? A commercial paint thinner gives two spots on chromatography and has 13C NMR peaks at 7.0, 27.5, 35.2, 45.3, 95.6, and 206.3 ppm. Suggest what compounds might be used in this thinner. Purpose of the problem To start you on the road to structure identification with one very simple problem and some deductive reasoning. It is necessary to think about the size of the chemical shifts to solve this problem. Suggested solution With the very small molecule C2H3Cl3 it is best to start by drawing all the possible structures. In fact there are only two. Me Cl Cl Cl Cl Cl Cl ■ The synthesis of methoxatin is described in J. A. Gainor and S. M. Weinreb, J. Org. Chem., 1982, 47, 2833. 1,2-diketone or ortho-quinone...
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