Benzene diazonium chloride is a organic compounds. in this article we know about how is benzene diazonium chloride prepared.
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What is benzene diazonium chloride?
It is an organic compound.
It is properly soluble in water.
Formula of this compund is [C6H5N2]Cl.
The chemical structure of this compound is,
You know that what is mean by Diazonium salt.
Diazo – two Nitrogen – N2
and nium mean – + charge and add + salt
Diazo + nium + salt = diazonium salt
You can write, Diazonium salt.
You can write in other form of Diazonium salt is,
R – N2+ (positive) + ions (X negative)
Where, ions may be (Cl negative), Br negative or HSO4 negative etc.
You can write;
R – N+ (positive) triple bond N Cl (negative)
Were, R- is alkyl or aryl
It is alkyl diazonium chloride
benzene diazonium chloride is very useful and very important organic compound.
It is use for preparation of many other important compound. Such as , benzene and phenol etc. It is produced verity of organic compound such as, benzene, nitrobenzene, phenol etc.
It is windly use in organic chemistry.
It is colourless crystal or colourless solid.
Properties of benzene diazonium Chloride?
Benzene diazonium chloride formula – C6H5CIN2.
Molar Mass – 140.57 g. Mol-1
Appearance – colourless crystalline.
Boiling point – decompose.
Solubility – very good, but it is react with it only when warmed.
Benzene diazonium Fluoroborate – Not soluble
Stability of benzene diazonium fluoroborate – at room temperature.
1. Benzene diazonium Chloride decomposes to phenol when temperature will high.
2. It is colourless crystalline
3. there is no melting point and boiling point, in this case melting point decomposes.
Formation of benzene diazonium chloride,
Formation of benzene diazonium chloride by Aniline
there are two best method which is use for formation of benzene diazonium Chloride by chemical reaction method and by laboratory methods.
(By Chemical reaction method)
- By Aniline –
In this reaction, you need aniline (NH2) on Benzene ring and add NaNO2 + HCl then it give benzene diazonium chloride as a product.
When aniline is react with sodium nitrate NaNO2 and (hydrochloric acid) HCl at 0 – 5°C then, it give benzene diazonium Chloride (Diazonium salt) as a product.
After reaction you can see First N2 is removed and sodium chloride (Nacl) is removed.
In this reaction, Na + Cl attached together and it form Nacl, that is called sodium chloride. and then water molecule is formed. In other words, two atoms of hydrogen and one atom of oxygen is attached together then it form water molecule, for example;
H2 + O = H20 (water molecule)
where H is Hydrogen and O is oxygen.
Mechanism behind this reaction,
First off all I m talking about , how to react NaNO2 and HCl each other.
You know that NaNO2 is also write in other form as shown in figure.
If sodium nitrate is react with hydrochloric acid then it give HNO2 + NaCl sodium chloride as shown in figure.
NaNO2 + HCl – HNO2 + NaCl
NaNO2 – sodium nitrate
HCl – hydrochloric acid
After reaction HNO2 or NaCl is formed.
HNO2 – H – O – N = O
O – oxygen, H – Hydrogen, N – Nitrogen
It is lone pair of the atoms.
You can see oxygen atoms is attack on HCl and a product is formed as shown in figure.
this this product is again react with hydrochloric acid HCl then oxygen is again attack on HCl then it give water molecule and nitrosonium ion as shown in second figure.
How is benzene diazonium Chloride prepared
By (Laboratory Method)
if you follow properly according to this flow chart it is easy to produce diazonium salt in laboratory.
Benzene diazonium chloride is very useful compound because it is produce different types of organic compound and it is windly use in organic chemistry. Now, i m going to explain in details about different reaction.
How to convert benzene diazonium chloride to phenol?
When Benzene diazonium chloride is treated with the presence of atmosphere for water then it give phenol product and N2 or hydrochloric acid (HCl) will remove as shown in figure.
In this reaction, first N2 will remove and chlorine Cl + H hydrogen is attached together and form hydrochloric acid (HCl).
After finally one hydrogen and one oxygen joined on Benzene ring and it make phenol.
C6H6+OH were as, O is oxygen and in this reaction H is Hydrogen, it mean,
One atoms of oxygen and one atom of hydrogen. If this to atom joined together on Benzene ring then it made phenol. and it called phenol product.
2. How will you convert benzene diazonium chloride to benzene?
When benzene diazonium chloride is treated with the presence of SnCl2 and sodium hydroxide (NaOH), it form Benzene product. HCl and N2 will removed as shown on figure.
3. How will you convert benzene diazonium chloride to ido benzene?
When Diazonium salt is react with the presence of potassium iodide (KI) then it give ido benzene and N2 and KCl is formed.
4. How will you convert benzene diazonium chloride to nitrobenzene?
When benzene diazonium chloride is react with NaNo2/ cu+ then it give nitrobenzene as a product.
Coupling reaction of benzene diazonium chloride
benzene diazonium chloride react with phenol, aniline, beta – nepthol. and in this reaction, colour compound (azo dye) is formed and hcl is eliminated.
- benzene diazonium chloride react with phenol
when benzene diazonium Chloride is react with phenol, yellow colour dye is formed as a product, and hcl is eliminated as shown in reaction.
- benzene diazonium chloride react with aniline
when benzene diazonium Chloride is react with aniline, red colour dye is formed as a product. this is called red azo dye. and hcl is eliminated. azo dye test is carried out from aromatic amines (aniline). Aniline is an aromatic amine and after this reaction with aniline it gives yellowish azo dye as a product.
- benzene diazonium chloride is react with beta – nephthol
when benzene diazonium chloride is react with beta – nephthol,
[napthelene + alcohol = beta nephthol], red colour dye is formed as a product. It is called red azo dye.
- Coupling reaction with aniline (Azo – N)
Aniline is directly reacted with benzene diazonium chloride and with maintain pH (> 7). then it make an azo colour component, this is called azo colour dye or azo dyes.
frequently Asked questions
1. Why benzene diazonium chloride is not stored?
It is not stored because it is stable in very short time. In other words it is instability so it is not stored. It is immediately used after preparation because stability is in short time other wise it reacts fast.
2. Which type of product is formed, when heat aquos solution of benzene diazonium chloride?
when on heat of aquoes solution of benzene diazonium chloride then only phenol is formed as a product.
3. What is the write method of preparation of benzene diazonium chloride?
Write method of preparation – when aniline is react with sodium nitriate NaNo2 and HCl at low temperature 0-5°C then it gives diazonium salt as a product. this is very simple method for preparation of diazonium salt.
4. What is the coupling reaction of benzene diazonium chloride?
In case of coupling reaction of diazonium salt, phenol, aniline, beta – nephthol. these are play important role in coupling reaction of diazonium salt. benzene diazonium chloride is react with phenol, it give yellow colour component, again it react with aniline then it give red colour component.
similarly, it again react with beta – nephthol then it give orange colour component. this reaction is know as coupling reaction of diazonium salt.