amines

AMINES THEORY

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Rule 1. Amines can be named as derivatives of alkylamines or alkanoamines. Let's see some examples.

amine nomenclature

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Amines have lower melting and boiling points than alcohols. Thus, ethylamine boils at 17ºC, while the boiling point of ethanol is 78ºC.

CH ₃ CH ₂ OH P.b. = 78ºC

CH ₃ CH ₂ NH ₂ P. eb. = 17ºC

The lower electronegativity of nitrogen, compared to that of oxygen, makes the hydrogen bonds formed by amines weaker than those formed by alcohols.

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Amines have acidic hydrogens on the amino group. These hydrogens can be subtracted using strong bases (organometallic, metal hydrides) forming amides (amine bases).

Methylamine [1] reacts with methyllithium, transforming into its conjugate base, lithium methylamide [2] . For its part, methyllithium is transformed into its conjugate acid, methane.

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Amines are nitrogenous compounds with a pyramidal structure, similar to ammonia. Nitrogen forms three single bonds through sp ³ . The lone pair occupies the fourth orbital with sp ³ and is responsible for the basic and nucleophilic behavior of amines.

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Amines can be prepared by nucleophilic substitution reactions between haloalkanes and ammonia.

The first equivalent of ammonia acts as a nucleophile, substituting for bromine. The second equivalent acts as the base by deprotonating the amine.

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Nitriles can be prepared by reacting haloalkanes with sodium cyanide. The reduction of nitriles with LiAlH ₄ produces amines.

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The reaction of primary and secondary haloalkanes with sodium azide produces alkylazides, which by reduction with LiAlH ₄ give rise to amides.

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Amides are reduced with LiAlH ₄ to form amines. The carbon number of the final amine is equal to that of the starting amide.

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Amides are converted to amines, with one less carbon, by treatment with bromine in a basic medium. This reaction is known as the Hofmann rearrangement.