Distinguishing those is more tricky and needs

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Unformatted text preview: more than one product. 3 4 Solutions Manual to accompany Organic Chemistry 2e Suggested solution The three compounds are easily drawn: one or other carbonyl group, or both, may be reduced. OH O OH H O ■ Calculations from D. H. Williams and Ian Fleming (2007), Spectroscopic methods in organic chemistry (6th edn) McGraw Hill, London, 2007 suggest about 80 ppm for the C–OH carbon in the ketone and about 60 ppm for the aldehyde. OH OH The third compound, the diol, has no carbonyl group in the 13C NMR spectrum or the infrared and has a molecular ion two mass units higher than the other two products. Distinguishing those is more tricky, and needs techniques you will meet in detail in chapter 18. The hydroxyketone has a conjugated carbonyl group (C=O stretch at about 1680 cm–...
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