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Benzene Diazonium Salts Overview

This document discusses diazonium salts, including their structure, method of preparation, properties, and reactions. Diazonium salts have the general formula RN2+X- and are prepared by the reaction of aromatic amines with nitrous acid. Benzenediazonium chloride is a colorless crystalline solid that is stable in the cold but decomposes when warmed. It undergoes various substitution reactions where the diazonium group is replaced by halides, cyanide, hydroxyl, or nitro groups. These reactions allow the synthesis of substituted aromatic compounds not achievable by direct substitution.

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192 views17 pages

Benzene Diazonium Salts Overview

This document discusses diazonium salts, including their structure, method of preparation, properties, and reactions. Diazonium salts have the general formula RN2+X- and are prepared by the reaction of aromatic amines with nitrous acid. Benzenediazonium chloride is a colorless crystalline solid that is stable in the cold but decomposes when warmed. It undergoes various substitution reactions where the diazonium group is replaced by halides, cyanide, hydroxyl, or nitro groups. These reactions allow the synthesis of substituted aromatic compounds not achievable by direct substitution.

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CHEMISTRY CLASS XII

UNIT 13
ORGANIC COMPOUNDS CONTAINING NITROGEN
PART II
DIAZONIUM SALTS

Prepared by
Mr, Sunil Urade, PGT Chemistry JNV
Chandrapur
Mr. G.T. Hirve, PGT Chemistry JNV Latur
Mr.Ajit Sharma, PGT Chemistry JNV
Gandhinagar
REGIONAL OFFICE, PUNE
OUTLINE
 Review of previous session
 Introduction:What are the diazonium salts?
 Structure
 Method of Preparation of benzenediazonium
chloride
 Physical Properties of benzenediazonium chloride
 Chemical properties of benzenediazonium chloride
 Importance
DIAZONIUM SALTS
 The diazonium salt have the general formula RN2+X-
where R stands for an aryl group and X- may be Cl- ,Br-,
HSO4- BF4- etc.
 They are named by suffixing diazonium to the name of
the parent hydrocarbon from which they are formed
 The N2+ group is called diazonium group.
 For example, C6H5N2+Cl- benzenediazoniumchloride
Stability of benzene diazonium salt
 The stability of benzenediazonium ion is
due to the resonance effect
Preparation (Diazotization)

 Benzenediazonium chloride is prepared by the


reaction of aniline with nitrous acid at 273-278K.
 Nitrous acid is produced in the reaction mixture by
the reaction of sodium nitrite with hydrochloric acid.
 The conversion of primary aromatic amines into
diazonium salts is known as diazotisation.
Physical Properties

 Benzenediazonium chloride is a colourless


crystalline solid.
 It is readily soluble in water and is stable in cold
but reacts with water when warmed

 It decomposes easily in the dry state

 Benzenediazonium fluoroborate is water


insoluble and stable at room temperature.
Chemical Reactions of Diazonium salt

Reactions involving displacement of Nitrogen

 Diazonium group being a very good leaving


group, is substituted by other groups such as Cl –, Br–,
I–, CN– and OH– which displace nitrogen from the
aromatic ring.

 The nitrogen formed escapes from the reaction


mixture as a gas.
1. Replacement by halide or cyanide ion:
Sandmeyer reaction : The Cl–, Br– and CN–
nucleophiles introduced in the benzene ring in the
presence of Cuprous ion.

Gatterman reaction :
2. Replacement by iodide ion:

3. Replacement by fluoride ion:


4. Replacement by H:
Certain mild reducing agents like phosphinic acid or
ethanol reduce diazonium salts to arenes and
themselves get oxidised to phosphorous acid and
ethanal, respectively.

5. Replacement by hydroxyl group:


6. Replacement by –NO2 group:
When diazonium fluoroborate is heated with
aqueous sodium nitrite solution in the presence of
copper, the diazonium group is replaced by –NO2
group.
Coupling reactions
Importance of Diazonium Salts in Synthesis
of aromatic Compounds

 Aryl fluorides and iodides cannot be prepared by


direct halogenation.
 The cyano group cannot be introduced by
nucleophilic substitution of chlorine in chlorobenzene
but cyanobenzene can be easily obtained from
diazonium salt.
 The replacement of diazo group by other groups is
helpful in preparing those substituted aromatic
compounds which cannot be prepared by direct
substitution in benzene or substituted benzene.
Summary

 Preparation of diazonium salt

 Important reactions of diazonium salts

The importance of diazonium salts in


organic synthesis.
R O PUNE
Home work

1.Writes short notes on the following


(i) Coupling reaction
(ii) Diazotisation
2 How will you convert
(i)Benzene diazonium chloride in to p-hydroxyazo
benzene
(ii)Benzene diazonium chloride in to p- aminoazo
benzene
Thanks

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