The oxime of benzaldehyde (C 6 H 5 CH: N OH), formed by the addition of hydroxylamine to the aldehyde, exhibits a characteristic behaviour when hydrochloric acid gas is passed into its ethereal solution, a second modification being produced.
Hantzsch, Ber., 18 99, 32, p. 3109; 1900, 33, p. 278.) It is generally accepted that the iso-diazo hydroxides possess the oxime structure R N: N OH.
With phenylhydrazine it forms a hydrazone, and with hydroxylamine an oxime, which exists in one form only; if, however, one of the phenyl groups in the oxime be substituted in any way then two stereo-isomeric oximes are produced (cf.
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.
Wohl forms the oxime and converts it into an acetylated nitrile by means of acetic anhydride and sodium acetate; ammoniacal silver nitrate solution removes hydrocyanic acid and the resulting acetate is hydrolysed by acting with ammonia to form an amide, which is finally decomposed with sulphuric acid.
It possesses all the characteristic properties of an aldehyde; being readily oxidized to benzoic acid; reducing solutions of silver salts; forming addition products with hydrogen, hydrocyanic acid and sodium bisulphite; and giving an oxime and a hydrazone.
The carbonyl group is not ketonic in character since it yields neither an oxime nor hydrazone.
Amino-cyclo-heptane (suberylamine) is obtained by the reduction of suberone oxime or by the action of sodium hypobromite on the amide of cycloheptane carboxylic acid.
Stereo-Isomerism); thus parachlorbenzophenone oxime exists in two different forms (V.
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.