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AMINE (((Definition (Making amines from halogenoalkanes), Ddeals with…
AMINE
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Ddeals with amines where the functional group is not attached directly to a benzene ring. Aromatic amines such as phenylamine (aniline) are usually made differently.
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The halogenoalkane is heated with a concentrated solution of ammonia in ethanol. The reaction is carried out in a sealed tube. You couldn't heat this mixture under reflux, because the ammonia would simply escape up the condenser as a gas.
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Preparation of amines from halogenoalkanes (also known as haloalkanes or alkyl halides) and from nitriles.
The reaction happens in two stages. In the first stage, a salt is formed - in this case, ethylammonium bromide. This is just like ammonium bromide, except that one of the hydrogens in the ammonium ion is replaced by an ethyl group.
CH3CH2Br + NH3 "→CH3CH2NH3 Br
There is then the possibility of a reversible reaction between this salt and excess ammonia in the mixture.
CH3CH2NH3 Br + NH3 ↔CH3CH2NH2 +NH4 Br
The ammonia removes a hydrogen ion from the ethylammonium ion to leave a primary amine - ethylamine.
The more ammonia there is in the mixture, the more the forward reaction is favoured.
The ethylamine also reacts with bromoethane - in the same two stages as before. In the first stage, you get a salt formed - this time, diethylammonium bromide. Think of this as ammonium bromide with two hydrogens replaced by ethyl groups.
CH3CH2Br + NH2 →CH3CH2NH2CH3CH2 Br
There is again the possibility of a reversible reaction between this salt and excess ammonia in the mixture.
CH3CH2NH2CH3CH2 Br + NH3 ↔ CH3CH2NHCH3CH2 + NH4 Br
The ammonia removes a hydrogen ion from the diethylammonium ion to leave a secondary amine - diethylamine. A secondary amine is one which has two alkyl groups attached to the nitrogen.
What is an AMINE?
DEFINITION
A compound in which one or more of the hydrogen atoms in ammonia have been replaced by an organic functional group.
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Generally weak bases, mostly organic bases.
CLASSIFICATION
Depending upon the number of hydrogen atoms that are replaced by an alkyl or aryl group in ammonia, amines are classified as primary (1'), secondary (2') and tertiary (3').
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If two of the three hydrogen atoms are replaced by alkyl/aryl groups then secondary amines are formed.
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A fourth subcategory is determined by the connectivity of the substituents attached to the nitrogen: Cyclic amines are either secondary or tertiary amines
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Sandmeyer Diazocoupling reaction is a chemical reaction used to synthesis aryl halides from aryl diazonium salts. 💫
The reaction is a method for substitution of an aromatic amino group via preparation of its diazonium salt followed by its displacement with a nucleophile, often catalyzed by copper(I) salts. The nucleophile can include halide anions, cyanide, thiols, water, and others.💫
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The Sandmeyer reaction provides a method of benzene transformation such as Halogenation, Cyanation, trifluoromethylation and hydroxylation 💫
The reaction was discovered in 1884 by Swiss chemist Traugott Sandmeyer, when he synthesized phenylacetylene from benzenediazonium chloride and cuprous acetylide.💫
Variations on the Sandmeyer reaction have been developed to fit multiple synthetic applications. These reactions typically proceed through the formation of an aryl diazonium salt followed by a reaction with a copper(I) salt to yield a substituted arene 💫
One of the most important uses of the Sandmeyer reaction is the formation of aryl halides. The solvent of choice for the synthesis of aryl iodides is diiodomethane,while for the synthesis of aryl bromides, bromoform is used. For the synthesis of aryl chlorides, chloroform is the solvent of choice. The synthesis of (+)-curcuphenol, a bioactive compound that displays antifungal and anticancer activity, employs the Sandmeyer reaction to substitute an amine group by a bromo group 💫
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