NITRILE THEORY

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NITRILE THEORY
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IUPAC names nitriles by adding the suffix -nitrile to the name of the alkane with the same number of carbons.

nitriles nomenclature1

[1] Methanenitrile

[2] Ethanenitrile

[3] Ethanedinitrile

[4] 3-Methylbutanenitrile

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NITRILE THEORY
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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.

sintesis-nitrilos

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NITRILE THEORY
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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.

hidrolisis-acida-nitrilos

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

hidrolisis-basica-nitrilos

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NITRILE THEORY
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The nitriles react with organometallic lithium or magnesium, to form ketones, after an acid hydrolysis step.

reaccion-nitrilos-organometalicos

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NITRILE THEORY
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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.

enolatos-nitrilo

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NITRILE THEORY
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Lithium aluminum hydride reduces nitriles to amines. The reaction is carried out in ether medium, followed by acid hydrolysis. reduccion-nitrilos-aminas

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NITRILE THEORY
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DIBAL (diisobutylaluminum hydride) reduces nitriles to aldehydes

nitrilos-reduccion-aldehidos