Oxime

Oxime is a functional group or chemical compound containing the oxygen and nitrogen atoms connected by a double bond. The general formula for an oxime is R1R2C=NOH, where R1 is an organic side chain and R2 may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. Oximes are usually generated by the reaction of hydroxylamine with aldehydes or ketones.

History

The oxime functional group was first synthesized in 1860 by the Russian chemist Alexander Butlerov. He produced it by reacting acetone with hydroxylamine.

Synthesis

Oximes are synthesized through the reaction of an aldehyde or ketone with hydroxylamine. The reaction is catalyzed by acid. The general formula for this reaction is R2C=O + NH2OH → R2C=NOH + H2O, where R is an organic side chain.

Properties

Oximes have a double bond between the nitrogen and oxygen atoms, and a single bond between the nitrogen atom and a hydrogen atom. They are polar compounds, due to the electronegativity difference between the oxygen and nitrogen atoms. Oximes are also capable of hydrogen bonding, which makes them soluble in water.

Applications

Oximes are used in organic chemistry as protective groups for aldehydes and ketones, and as reagents in the preparation of amines. They are also used in the medical field for the treatment of certain types of poisoning.

See also

• Hydroxylamine
• Aldehyde
• Ketone
• Alexander Butlerov

References

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