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Reaction of aldehydes and ketones with hydroxylamine gives oximes. The nucleophilicity of the nitrogen on the hydroxylamine is increased by the presence of the oxygen. Successive proton transfers allows for elimination of water. Oximes generally form a mixture of geometric isomers.
S. Rosenberg, S. M. Silver, J. M. Sayer and W. P. Jencks, J. Am. Chem. Soc., 1974, 96, 7986–7998.
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