Diazonium Salts
Diazonium Salts
Diazonium Salts
2 Diazonium Salts:
SYBSC SEMESTER-4
ORGANIC CHEMISTRY
PAPER-2
05-02-2021
Diazonium salts, S.Y.BSc. Organic Chemistry by Dr.K.T.Waghmode
3 Diazonium salts
Diazonium compounds or diazonium salts are a
group of functional group R−N + 2X − where R can be
any organic compounds sharing a common group,
such as an alkyl or an aryl, and X is an inorganic or
organic monovalent anion, such as a halogen, -OH
etc.
Nitrosonium ion
1.Replacement of diazonium
group by halogens:
The nitrous acid is typically prepared in situ from sodium nitrite and
acid.
Following two protonation steps, one equivalent of water is lost to form
the nitrosonium ion.
The nitrosonium ion then acts as an electrophile in a reaction with
an aromatic (or heterocyclic) amine, such as aniline, to form a
diazonium salt, proceeding through a nitrosamine intermediate
- -
CuCl + Cl CuCl 2
+
C6H5N2+ C6H5 + N2
- Fast
C6H5N2+
+ Cl Cu C6H5Cl + CuCl
Cl
+ -
N2 Cl
I
+ KI
+ KCl + N 2
+ HBF4
+ HCl
Fluoroboric acid
+ -
N2 BF4 F
+ BF3 + N2
05-02-2021
Diazonium salts, S.Y.BSc. Organic Chemistry by Dr.K.T.Waghmode
40 7.Azocoupling reaction