The compound exists as a stable hemiacetal because it

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Unformatted text preview: or Chapter 6 – Nucleophilic Addition to the Carbonyl Group carbonyl group is not stabilised by conjugation and is destabilised by two other ketones so it forms the hydrate. Did you remember that hydrate formation is thermodynamically controlled? O OH OH O PROBLEM 6 This hydroxyketone shows no peaks in its infrared spectrum between 1600 and 1800 cm–1, but it does show a broad absorption at 3000–3400 cm–1. In the 13C NMR spectrum there are no peaks above 150 ppm but there is a peak at 110 ppm. Suggest an explanation. O HO Purpose of the problem Structure determination to solve a conundrum. Suggested solution The evidence shows that there is no carbonyl group in the molecule but that there is an OH group. The peak at 110 ppm looks a...
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