Depto. Química Orgánica

PREPARATION OF NITRILES

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15/07/2017
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The nitrile function can easily be introduced by reaction of cyanide, either by substitution or addition.
Nucleophilic Substitution
The substitution of a good leaving group by cyanide is a simple and general reaction to get nitriles. Click here to remember the competition between substitution and elimination.
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Diazonium Salts Displacement
Diazonium salts are prepared by the action of nitrous acid on anilines.
 Click here to recall the versatility of diazonium salts.
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Cyanide Addition to Aldehydes and Ketones
The perhaps simplest carbon nucleophile, cyanide, adds to aldehydes and ketones to render cyanohydrins.
Click here to remember cyanohydrins in their context.
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Conjugated Addition to alpha,beta-Unsaturated Compounds
Cyanide adds to alpha,beta-unsaturated aldehydes, ketones, esters, amides, etc in a totally conjugated manner (Michael addition). Click here to review the reaction in its context.
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Aldoxime Dehydration
Aldoximes are obtained by reaction of hydroxylamine with aldehydes.
Their dehydration with a water avid compound like an anhydride, leads to a nitrile.
Click here to remember what an oxime is.
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Amide Dehydration
Primary amides can be dehydrated with strong dehydrating agents like phosphorous pentoxide yielding nitriles.
Click here to recall what an amide is.
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