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Describe a method for the preparation of haloarenes from diazonium salts.

Question

Describe a method for the preparation of haloarenes from diazonium salts.

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Solution

The preparation of haloarenes from diazonium salts involves the Sandmeyer reaction. Here are the steps:

  1. Diazotization: The first step is the preparation of diazonium salt from aniline. Aniline is treated with nitrous acid (prepared from sodium nitrite and hydrochloric acid) at 0-5°C to form a diazonium salt.

  2. Sandmeyer Reaction: The diazonium salt is then treated with copper powder and a halogen (Cl, Br, or I) in the presence of hydrochloric acid. This results in the formation of a haloarene.

Here is the general reaction:

ArNH2 + NaNO2 + HCl → ArN2+Cl- (Diazonium salt) ArN2+Cl- + Cu + X2 → ArX + N2 + CuX (X = Cl, Br, I)

In this reaction, Ar represents an aryl group, X represents a halogen, and N2 represents nitrogen gas. The nitrogen gas is released as a byproduct.

This method is commonly used for the preparation of chlorobenzene and bromobenzene. It's important to note that this reaction must be carried out at a low temperature to prevent the decomposition of the diazonium salt.

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Many halogen containingorganic compounds occur in nature and some ofthese are clinically useful. These classes of compoundsfind wide applications in industry as well as in day-to-day life. They are used as solvents for relativelynon-polar compounds and as starting materials forthe synthesis of wide range of organic compounds.Chlorine containing antibiotic, chloramphenicol,produced by microorganisms is very effective for thetreatment of typhoid fever. Our body produces iodinecontaining hormone, thyroxine, the deficiency of whichcauses a disease called goiter. Synthetic halogencompounds, viz. chloroquine is used for the treatmentof malaria; halothane is used as an anaestheticduring surgery. Certain fully fluorinated compoundsare being considered as potential blood substitutesin surgery

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