Nitrile: Difference between revisions
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A '''nitrile''' is an organic compound containing a carbon triple bonded to nitrogen. | A '''nitrile''' is an organic compound containing a carbon triple bonded to nitrogen. | ||
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*The '''Sandmeyer reaction''' employing cuprous cyanide can be used to form nitriles from diazonium compounds. | *The '''Sandmeyer reaction''' employing cuprous cyanide can be used to form nitriles from diazonium compounds. | ||
*Aryl nitriles may be formed from aryl halides in the '''Rosenmund-von Braun reaction'''. | *Aryl nitriles may be formed from aryl halides in the '''Rosenmund-von Braun reaction'''. | ||
*The reaction of cyanide with aldehydes or ketones forms a cyanohydrin (ά-hydroxynitrile). | |||
*Amides may be dehydrated to nitriles with a variety of reagents | |||
==Reactivity== | ==Reactivity== | ||
*Nitriles are reduced to [[amine|amines]] by [[hydrogen]] and a [[nickel]] catalyst | |||
*Nitriles are reduced to imines, then hydrolyzed to the aldehyde in the '''Stephens aldehyde synthesis'''. | *Nitriles are reduced to imines, then hydrolyzed to the aldehyde in the '''Stephens aldehyde synthesis'''. | ||
*Beta-ketoesters are formed from alpha-bromoesters and nitriles in the '''Blaise reaction'''. | *Beta-ketoesters are formed from alpha-bromoesters and nitriles in the '''Blaise reaction'''. | ||
*Nitriles are hydrolysed to [[amide|amides]] by acid | |||
Latest revision as of 16:46, 28 October 2010
A nitrile is an organic compound containing a carbon triple bonded to nitrogen.
Synthesis
- The Sandmeyer reaction employing cuprous cyanide can be used to form nitriles from diazonium compounds.
- Aryl nitriles may be formed from aryl halides in the Rosenmund-von Braun reaction.
- The reaction of cyanide with aldehydes or ketones forms a cyanohydrin (ά-hydroxynitrile).
- Amides may be dehydrated to nitriles with a variety of reagents