AMIDES THEORY

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AMIDES THEORY
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Amides are named as derivatives of carboxylic acids by substituting the -oic ending of the acid for -amide .

amides1 nomenclature

[1] Methanamide

[2] Ethanamide

[3] N-Methylpropanamide

[3] N,N-Dimethylbutanamide

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AMIDES THEORY
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a) Amides can be obtained by reacting amines with alkanoyl halides and anhydrides .

Ethanoyl chloride reacts with two equivalents of methylamine to form ethanamide.
sintesis-amidas
 
The second equivalent of amine is used to collect the hydrochloric acid and favor the equilibria.
 
sintesis-amidas
Ethanoic anhydride reacts with ammonia to form ethanamine and ethanoic acid.

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AMIDES THEORY
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Lactams are cyclic amides obtained by condensation, with loss of water, of a molecule containing acid and amino groups.

lactamas
4-(aminomethyl)butanoic acid [1] condenses under heating to form N-methylpyrrolidin-2-one [2] , a polar aprotic solvent.

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AMIDES THEORY
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Imides are compounds that contain two acyl groups attached to a nitrogen by single bonds. Succinimide and Phthalimide are well known.

imidas

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AMIDES THEORY
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Amides hydrolyze in acidic media, under heating, forming amines and carboxylic acids.

hidrolisis-acida

Ethanamide hydrolyzes in a sulfuric medium to form ethanoic acid .

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AMIDES THEORY
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The amides are transformed into amines and carboxylic acids by treatment with aqueous soda under heating.

 
hidrolisis-basica-amidas
 
Ethanamide hydrolyzes in the presence of aqueous soda to form sodium ethanoate.

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AMIDES THEORY
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The amides have acidic hydrogens of Pka = 15 on the nitrogen atom. Deprotonation of the amino generates a resonance stabilized base, called amidate.

 
amidatos-01.png

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AMIDES THEORY
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The amides present acidic hydrogens of Pka = 30 on the carbon a . Deprotonation of the a position generates a resonance stabilized base, called the amide enolate.

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AMIDES THEORY
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Lithium aluminum hydride reduces amides to amines.

reduccion-amidas

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AMIDES THEORY
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Diisobutyl aluminum hydride (DIBAL) reduces amides to aldehydes

reduccion-amidas-aldehidos

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AMIDES THEORY
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Amides are transformed into amines with one less carbon, when treated with bromine in basic solution.

 
transposicion-hofmann
 
Acetamide [1] reacts with bromine in a basic medium, transforming into methylamine [2] with the loss of carbon dioxide.