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Nucleophilic Addition vs. Substituion: A Puzzle for the Organic LaboratoryErnest F. Silversmith The chemistry of beta-carbonyl compounds is studied. Beta-carbonyl compounds react with hydrazines to give products with a 5-membered ring containing two nitrogens. The experiment makes students determine whether ethyl 2-acetyl-3-oxobutanoate reacts like a beta-diketone or like a beta-keto ester. Silversmith, Ernest F. J. Chem. Educ.1998, 75, 221.