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17 Reactions of Aromatic Compounds -- Part 13
The diagram shows the reaction of an amine with water.
The reactants on the left are free amine and water.
The products are on the right.
The amine is a stronger base if structural features shift the reaction toward the right.
The free amine is weakened by features that shift the reaction to the left.
Consider the relative basicities of ammonia and methylamine.
Alkyl groups are moving toward cations and methylamine is moving toward nitrogen.
The stabilization lowers the potential energy of the cation, making it a stronger base than ammonia.
The alkylamines are stronger than ammonia.
We might expect secondary amines to be stronger than primary amines, and tertiary amines to be the strongest bases.
solvation effects make the situation more complicated.
The energy of solvation contributes to their stability because they are solvated by water.
There are more alkyl groups around the secondary and tertiary amines that make it harder for water to approach them.
Arylamines and their derivatives are not as strong as simple aliphatic amines.
The free amine has resonance delocalization of the nonbonding electrons.
The aromatic ring and the orbital containing nitrogen's lone pair are related in aniline.
This overlap is lost in the anilinium ion, so the reactant is stable compared with the product.
Aniline is less basic than most aliphatic amines.
The basicity of pyrrole is influenced by resonance effects.
pyrrole loses its aromatic stabilization when it is protonated.
pyrrole is a very weak base because of the unfavorable protonsation on nitrogen.
The study of terminal alkynes showed that it's basic than aliphatic amines.
When the nitrogen atom is used to explain why the amine is weaker than the aliphatic, this principle helps true.
The nitrogen atom is bonding aliphatic amine.
As in aniline, a protons, Pyridine's nonbonding electrons are less available for bonding to the aromatic ring.
Pyridine is a resonance effect and does not lose its aromaticity.
A concentrated mineral acid is required to make acetonitrile.
In order to increase basicity, rank each set of compounds.
The amine salt is composed of two different types of ion.
Salts of amine and acid are used to make them.
Amine salts are nonvolatile.
They are more water-soluble than the parent amine.
Formation of amine salts can be used.
Water is relatively insoluble in amine containing more than six carbon atoms.
It was originally used to treat asthma.
The remedy is advertised as a "natural" dissolve because of the amine form of the acid.
One of the tests of a functional group is the formation of a salt.
The amine is mostly dissolved in the ether layer when shaken with a two-phase mixture of ether and water.
An amine can be used for purification.
The amine is more stable in ether than in water.
The water-soluble HCl is converted to the water-soluble salt.
The free amine is regenerated by neutralization.
Add a fresh ether phase by draining off the ether.
The amine is deprotonated by adding NaOH to the solution.
The pure amine is created by dissolving the free amine in the fresh ether phase.
Many drugs and amines are stored and used as salts.
Amine salts have no fishy odor and are less prone to decomposition by oxidation and other reactions.
The salts are easy to convert to solutions for syrups and injections.
The drug ephedrine is used in cold and allergy medication.
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