Organic reaction

mechanisms
5. Organic reactions and
mechanism
L12: Diazotization and coupling

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Azo compounds
 Azo compounds are
those organic compounds
which contain one or
more azo groups in their
structure. Azo group is
very important as it is a
part of a large group of
dyes called azo dyes.

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Azo compounds
 The preparation of azo compounds consists of
two consequent reactions diazotization and
coupling. These two are the basic steps in the
manufacture of azo dyes.

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Diazotization
 The process of diazotization begins with the formation of
NO+ species which is a highly reactive cation. An
aqueous solution of sodium nitrite is treated slowly with
hydrochloric acid whereby the following reaction takes
place.

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Diazotization
 NO+ formed in the previous reaction, now reacts with an amino
group by receiving the non bonding pair of electrons of amino
nitrogen to make a covalent bond. A hydrogen ion is eliminated
then. The specie formed now rearranges, and the oxy and hydroxy
compounds stay in equilibrium. The elimination of hydroxy group is
facilitated by protonation of hydroxy compound and elimination of a
water molecule.

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Diazotization
 Overall process of diazotization is as follows:

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coupling
 Coupling reaction is actually the coupling of diazonium
compound with another specie using the diazo group.
The diazo group is changed to azo group which acts as a
link between the two species.

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Acid dyes – acid red
 An example of a dye prepared by this process is
the acid red dye with is use to dye silk, wool,
leather and other polyamides.