Amines

Amines constitute an important class of organic compounds derived by replacing one or

more hydrogen atoms of ammonia molecule by alkyl/aryl group(s).
In nature, they occur among proteins, vitamins, alkaloids (eg. Morphine) and hormones.
Synthetic amines : polymers, dye stuffs and drugs.
Two biologically active compounds, namely adrenaline (hormone from adrenal gland) and
ephedrine ( obtained from plant Ephedra, used as medication and stimulant), both
containing secondary amino group, are used to increase blood pressure.
Novocain, a synthetic amino compound, is used as an anaesthetic in dentistry.
Benadryl, a well known antihistaminic drug (prevents action of histamine. Histamine is
secreted by immune cells of body as a response to any foreign agent) also contains tertiary
amino group.
Quaternary ammonium salts are used as surfactants (in detergents).
Diazonium salts are intermediates in the preparation of a variety of aromatic compounds
including dyes.

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Nature :
The lower aliphatic amines gases fishy odour.
Primary amines (three or more carbon atoms) liquid
Higher ones solid
Colour :
Aniline and other arylamines are usually colourless but get coloured on storage due to atmospheric oxidation.
Solubility in water :
Lower aliphatic amines Soluble in water
High molecular mass amines Solubility decreases
Why lower amines are soluble in water ? because they can form hydrogen bonds with water molecules.

why solubility decreases with increase in molar mass of amines ?

Ans. due to increase in size of the hydrophobic alkyl part. Higher amines are essentially insoluble in water.

electronegativity of nitrogen of amine 3.0

Electronegativity of oxygen of alcohol 3.5

Out of butan-1-ol and butan-1-amine, which will be more soluble in water and why?

O of butanol (an alcohol) forms stronger hydrogen bond with water molecules than N of butanamine (an
amine), and hence butanol is more soluble in water as compared to butanamine. (electronegativity)
Solubility in organic solvent :
Amines are soluble in organic solvents like alcohol, ether and benzene.
Polarity : alcohols > amines and form stronger intermolecular hydrogen bonds than amines.
Amines are less polar than alcohols, i.e. more non polar than alcohols.

Primary and secondary amines are engaged in intermolecular association due to hydrogen bonding between
nitrogen of one and hydrogen of another molecule. (see image)
This intermolecular association is more in primary amines than in secondary amines as there are two hydrogen
atoms available for hydrogen bond formation in it.
Tertiary amines do not have intermolecular association due to the absence of hydrogen atom available for
hydrogen bond formation.
Intermolecular association : primary amine > secondary amine

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Write chemical equations for the following reactions:
(i) Reaction of ethanolic NH3 with C2H5Cl.
(ii) Ammonolysis of benzyl chloride and reaction of amine so formed with two moles of CH3Cl.

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