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Introduction Amines-----
Objectives
After studying this Unit, you will be
able to
• describe amines as derivatives of
ammonia having a pyramidal
structure;
• classify amines as primary,
secondary and tertiary;
• name amines by common names
and IUPAC system;
• describe some of the important
methods of preparation of amines;
• explain the properties of amines;
• distinguish between primary,
secondary and tertiary amines;
• describe the method of prepara-
tion of diazonium salts and their
importance in the synthesis of a
series of aromatic compounds
including azo dyes.
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 and hormones. Synthetic examples include polymers,
dyestuffs and drugs.
Two biologically active compounds,
namely adrenaline and ephedrine, both containing Seccondary 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 also contains tertiary amino
group.
Quaternary ammonium salts are used
surfactants. Diazonium salts are intermediates in the Preparation of a variety of aromatic compounds including dyes. In this Unit, you will learn about amines and diazonium salts.
I. AMINES
Amines can be considered as derivatives of ammonia, obtained by replacement of one, two or all the three hydrogen atoms by alkyl and/or aryl groups.
For example:
Like ammonia, nitrogen atom of amines is trivalent and Carries an unshared pair of electrons. Nitrogenorbitals
in amines are therefore, sp3
hybridised and the geometry
of amines is pyramidal. Each of the three sp3
hybridised
orbitals of nitrogen overlap with orbitals of hydrogen or
carbon depending upon the composition of the amines.
The fourth orbital of nitrogen in all amines contains an
unshared pair of electrons.
Gabriel synthesis is used for the preparation of primary amines.
watch video
Phthalimide on treatment with ethanolic potassium hydroxide formspotassium salt of phthalimide which on heating with alkyl halide f ollowed by alkaline hydrolysis produces the corresponding primary amine. Aromatic primary amines cannot be prepared by this method
because aryl halides do not undergo nucleophilic substitution with
https://youtu.be/vZymjz4dyXY the anion formed by phthalimide.
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