You are advised to make a good drawing of the molecule

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Unformatted text preview: 191, 193, and 194 at 6.6% of the peak before it. Compounds (a) and (c) might be isomers of compounds such as these: Br Br Cl Br Br OH Cl Cl ■ Buckminsterfullerene is on page 25 of the textbook. 2 Solutions Manual to accompany Organic Chemistry 2e PROBLEM 2 Ethyl benzoate PhCO2Et has these peaks in its 13C NMR spectrum: 17.3, 61.1, 100- 150 (four peaks) and 166.8 ppm. Which peak belongs to which carbon atom? You are advised to make a good drawing of the molecule before you answer. ■ These regions are described on on page 56 of the textbook. Purpose of the problem To familiarize you with the four regions of the spectrum. Suggested solution It isn’t possible to say which aromatic carbon is which and it doesn’t matter. The rest are straightforward. δ 100-150 four types of aromatic carbon: δ 166.8 carbonyl O δ 61.1 saturated carbon next to oxygen ortho meta para meta ipso O ortho δ 17.3 saturated carbon not next to oxygen PROBLEM 3 Methoxatin was mentioned on page 44 of the textbook where we said ‘it proved exceptionally difficult to solve the structure by NMR.’ Why is it so difficult? Could anything be gained from the 13C or 1H NMR? What information could be gained from the mass spectrum and the infra red? Purpose of the problem To convince you that this structure really needs an X- ray solution but also to get you to think about what information is available by the other methods. Certainly mass spectroscopy, NMR, and IR would have been tried first. Suggested solution There are only two hydrogens on carbon atoms and they are both on aromatic rings. There are only two types of carbon atom: carbonyl groups and unsaturated ring atoms. This inf...
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