any of a series of compounds formed by the action of hydroxylamine on an aldehyde or ketone, in which the oxygen atom of the CHO group of the aldehyde, or of the CO group of the ketone, is replaced by the :NOH group
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Any of a group of compounds containing a hydroxyl group bonded to a carbon atom, which in turn is doubly bonded to a nitrogen atom. An oxime is formed by treating an aldehyde or ketone with hydroxylamine.
The carbonyl group is not ketonic in character since it yields neither an oxime nor hydrazone.
The carbonyl oxygen may also be replaced by the oxime group,: N OH; thus the acids yield the hydroxamic acids, R C(OH): NOH, and the acid-amides the amidoximes, R C(NH 2): NOH.
Beckmann, Ber., 1886, 1 9, p. 9 8 9; 188 7, 20, p. 2580), yielding as final products an acid-amide or anilide, thus: RC(:N OH)R'-RC(OH) :NR' ---> As regards the constitution of the oximes, two possibilities exist, namely >C: NOH, or > C' ?, and the first of these is presumably correct, since on alkylation and subsequent hydrolysis an alkyl hydroxylamine of the type NH 2 OR is obtained, and consequently it is to be presumed that in the alkylated oxime, the alkyl group is attached to oxygen, and the oxime itself therefore contains the hydroxyl group. It is to be noted that the oximes of aromatic aldehydes and of unsymmetrical aromatic ketones frequently exist in isomeric forms. This isomerism is explained by the HantzschWerner hypothesis (Ber., 1890, 23, p. II) in which the assumption is made that the three valencies of the nitrogen atom do not lie in the same plane.
HO N Aldoximes are generally obtained by the action of hydroxylamine hydrochloride on the aldehyde in presence of sodium carbonate; the oxime being then usually extracted from the solution by ether.
Soc., 18 9 8, 73, p. 35 2) as a colourless liquid by the addition of hydroxylamine hydrochloride to an aqueous solution of formaldehyde in the presence of sodium carbonate; the resulting solution was extracted with ether and the oxime hydrochloride precipitated by gaseous hydrochloric acid, the precipitate being then dissolved in water, the solution exactly neutralized and distilled.