The central solutions for chapter 6 nucleophilic

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Unformatted text preview: 1 in the infrared spectrum) while the hydroxyaldehyde is not conjugated (C=O stretch at about 1730 cm–1 in the infrared). The chemical shift of the C–OH carbons will also be different because the benzene ring is joined to this carbon in the aldehyde but not in the ketone. PROBLEM 5 The triketone shown here is called ‘ninhydrin’ and is used for the detection of amino acids. It exists in aqueous solution as a hydrate. Which ketone is hydrated and why? O O O Purpose of the problem To let you think practically about reactions that may give more than one product. Suggested solution The two ketones next to the benzene ring are stabilised by conjugation with it but also destabilised by the central ketone—two electron- withdrawing groups next to each other is a bad thing. The central Solutions f...
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