Hydroxylamine
Hydroxylamine is the inorganic compound NH₂OH, with an amino group bonded to a hydroxyl group. It is a reactive reagent used in chemical synthesis.
Oxime: An oxime is a compound containing a carbon–nitrogen double bond with a hydroxyl group attached to nitrogen. Hydroxylamine converts aldehydes and ketones into oximes by replacing their carbonyl oxygen.
Carbonyl compound: A carbonyl compound contains a carbon–oxygen double bond, as in aldehydes, ketones, and carboxylic acid derivatives. Aldehydes and ketones are converted to oximes using hydroxylamine.
Amine: An amine is an organic derivative of ammonia in which one or more hydrogen atoms are replaced by carbon-containing groups. Hydroxylamine’s nitrogen resembles amine nitrogen but is bonded to oxygen rather than carbon or hydrogen alone.
Ammonia: Ammonia is the nitrogen hydride NH₃, a pungent gas and weak base. Replacing one ammonia hydrogen with hydroxyl gives hydroxylamine and substantially changes its reactivity.
Nucleophilic addition: Nucleophilic addition is a reaction in which a nucleophile bonds to an electrophilic atom, usually across a multiple bond. Hydroxylamine adds to carbonyl groups before dehydration yields oximes.
Caprolactam: Caprolactam is a cyclic amide used as the principal monomer for producing nylon 6. Its industrial route commonly passes through cyclohexanone oxime, made using hydroxylamine.
Hydroxyl group: A hydroxyl group is an –OH functional group bonded to another atom or molecular group. The N–O bond places a hydroxyl group directly on hydroxylamine’s nitrogen.
Hydrazine: Hydrazine is the inorganic compound N₂H₄, with two nitrogen atoms joined by a single bond. Hydrazine is a related reducing agent but contains an N–N bond instead of hydroxylamine’s N–O bond.
Beckmann rearrangement: The Beckmann rearrangement converts oximes into amides or, from cyclic ketoximes, ring-expanded lactams. Oximes made with hydroxylamine are common starting materials for this rearrangement.
Nitrile oxide: A nitrile oxide is a reactive 1,3-dipole with the structure R–C≡N⁺–O⁻. Hydroxamoyl halides derived from hydroxylamine can eliminate hydrogen halide to form nitrile oxides.