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acid in the presence of ethyl nitrate

Hydroxylamine reacts with electrophiles, such as alkylating agents, which can attach to either the oxygen or the nitrogen atoms:

R-X + NH2OH → R-ONH2 + HX
The reaction of NH2OH with an aldehyde or ketone produces an oxime.

R2C=O + NH2OH∙HCl , NaOH → R2C=NOH + NaCl + H2O
This reaction is useful in the purification of ketones and aldehydes: if hydroxylamine is added to an aldehyde or ketone in solution, an oxime forms, which generally precipitates from solution; heating the precipitate with an inorganic acid then restores the original aldehyde or ketone.[12]

Oximes, e.g., dimethylglyoxime, are also employed as ligands.

NH2OH reacts with chlorosulfonic acid to give hydroxylamine-O-sulfonic acid, a useful reagent for the synthesis of caprolactam.

The hydroxylamine-O-sulfonic acid, which should be stored at 0 °C to prevent decomposition, can be checked by iodometric titration.[clarification needed]

Hydroxylamine (NH2OH), or hydroxylamines (R-NHOH) can be reduced to amines.[13]

NH2OH (Zn/HCl) → NH3
R-NHOH (Zn/HCl) → R-NH2
Hydroxylamine explodes with heat:

4 NH2OH + O2 → 2 N2 + 6 H2O
The high reactivity comes in part from the partial isomerisation of the NH2OH structure to ammonia oxide (also known as azane oxide), with structure NH3+O−.