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 nomenclature1

Ethylamine (Ethanamine)

Cyclopentylamine (Cyclopentanamine)

(Pent-2-yl)amine (Pentan-2-amine)

Read more: 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 reacts with methyllithium, transforming into its conjugate base, lithium methylamide . 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 -hybridized orbitals. The lone pair occupies the fourth orbital with sp ³ hybridization 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 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.