NITRILE THEORY
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- Germán Fernández
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IUPAC names nitriles by adding the suffix -nitrile to the name of the alkane with the same number of carbons.
[1] Methanenitrile
[2] Ethanenitrile
[3] Ethanedinitrile
[4] 3-Methylbutanenitrile
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a) From haloalkanes: Nitriles can be prepared from haloalkanes, by SN2 processes. The reaction gives good performance with primary and secondary substrates, the tertiary ones are preferentially eliminated, forming alkenes.

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Nitriles hydrolyze in acidic media, under heating, becoming carboxylic acids and ammonium salts. The hydrolysis of nitriles is an irreversible process.

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The nitriles are hydrolyzed with aqueous soda, under heating, to form carboxylates and ammonia.

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Nitriles present hydrogens to acids that can be removed with strong bases, forming nitrile enolates. These hydrogens have a pKa of 25.

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DIBAL (diisobutylaluminum hydride) reduces nitriles to aldehydes
