Note on Haloarenes and Method of preparation of Haloarenes

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Haloarenes

Haloarenes are the halogen derivatives of aromatic hydrocarbons in which halogen is directly attached to the ring. these are obtained by replacing hydrogen by alpha-halogen atom.

$$Ar-H\xrightarrow{-H\,/+X}Ar-X$$

$$Where\,Ar-H=Aromatic\,substution$$

$$Ar-X=Haloarene$$

Nomenclature.

Monosubstituted haloarenes.

hygu
Disubstituted and polysubstituted haloarenes.


ghb

A general method for preparation of Haloarenes.

1. By direct halogenation of aromatic hydrocarbon.

$$Ar-H+X(Cl\,orBr)\xrightarrow{lewis\,acid\,dark}Ar-X+HX$$

$$Ar-H=Aromatic\,hydrocarbon$$

$$Ar-X=Haloarenes$$

Aromatic hydrocarbon is hydrogenated directly at dark in presence of Lewis acid such as AlCl3, FeCl3, FeBr3 to produce corresponding haloalkanes.

The reaction of an aromatic hydrocarbon with iodine is reversible. Therefore, iodination is carried out in presence of oxidation agent like HNO3, HIO3 etc. with accelerate the rate of forward reaction.

$$HIO_3+5HI→3H_2O+3I_2$$

2. From diazonium salts.

Diazonium salts. is obtained by adding the ice-cold solution of NaNO2 slowly on aniline in HCl. This reaction is Known as diazotization.

$$NaNO_2+HCl\xrightarrow{<5^0C}HNO_2+NaCl$$

$$Where\,HNO_2=Nitrous\,acid$$

Preparation of Chlorobenzene

1. From benzene.

When benzene is chlorinated directly with Cl2 in presence of FeCl3 at room temperature chlorobenzene is obtained.

Halogenation

2. From Aniline.

To get chlorobenzene from aniline,aniline is first converted into benzene diazonium chloride.

The product thus obtained is then reacted with Cu2Cl2 in presence of HCl to get chlorobenzene.

Image result for benzenediazonium chloride and chloro benzene

3. From phenol.

For that, phenol is first refluxed with Zn-dust to get benzene.

Image result for phenol into benzene

Then chlorination of benzene is carried out as to get chlorobenzene.

Image result for benzene into chlorobenzene

Preparation of chloroand bromobenzene (Sandmeyers reaction).

When benzene diazonium chloride is treated with (Cu2Cl2+HCl) and (Cu2Br2+HBr)separately. corresponding chlorobenzene and bromobenzene are formed. This reaction is called Sandmeyers reaction.

Image result for sandmeyer reaction

Preparation of Iodobenzene.

Benzene in presence of I2 and HNO3 give IOdobenzene

Image result for iodobenzene

Iodobenzene is obtained by adding aueousKI solution to benzene diazonium chloride.

Image result for iodobenzene from benzene diazonium chloride

Preperation of fluoro benzene (Balz-schiemann reaction)

Image result for fluoro benzene from aniline

Image result for fluoro benzene from aniline

Reference.

Bahl, B S, Bahl, and Arun. Advanced Organic chemistry. S. Chand and company Ltd., n.d.

Sthapit, M K, R R Pradhananga, and K B Bajracharya. Foundations of chemistry. Taleju Prakashan, n.d.

Tewari, K S, S N Mehrotra, and N K Vishnoi. A textbook of organic chemistry. Vikash publishing House Pvt. ltd., n.d.

Verma, N K and S K Khanna. Compressive chemistry. 8th edition. Laxmi publications P. Ltd., 1999.

  1. Haloarenes are the halogen derivatives of aromatic hydrocarbons in which halogen is directly attached to the ring. these are obtained by replacing hydrogen by alpha-halogen atom.
  2. Aromatic hydrocarbon is hydrogenated directly at dark in presence of Lewis acid such as AlCl3, FeCl3, FeBr3 to produce corresponding haloalkanes.

  3. To get chlorobenzene from aniline,aniline is first converted into benzene diazonium chloride.
.

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