What Is Stephen Reaction?

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The Stephen reaction is a chemical reaction used to prepare alkyl cyanides from primary halides. It is named after the British chemist Henry Stephen, who first described the reaction in 1873. The Stephen reaction is an important tool in organic synthesis and is used in the production of a wide variety of organic compounds. In this blog post, we will discuss what the Stephen reaction is, how it works, and its applications in organic chemistry.

What Is Stephen Reaction?

The Stephen reaction is a nucleophilic substitution reaction in which a primary halide is reacted with a cyanide ion to form an alkyl cyanide. The reaction is typically carried out in the presence of a catalyst, such as copper(I) cyanide or cuprous cyanide, which helps to facilitate the reaction.

The general equation for the Stephen reaction is:

R-X + NaCN → R-CN + NaX

Where R is the alkyl group and X is the halogen atom (e.g., Cl, Br, I).

How Does The Stephen Reaction Work?

The mechanism of the Stephen reaction involves the formation of an intermediate that is attacked by the cyanide ion. The reaction proceeds in two steps: first, the halide ion is displaced by the cyanide ion to form an intermediate alkyl cyanide, and second, the intermediate alkyl cyanide is deprotonated by the cyanide ion to give the final product.

The reaction is typically carried out in an aprotic solvent, such as dimethylformamide (DMF), to facilitate the formation of the intermediate.

Applications Of The Stephen Reaction

The Stephen reaction is an important tool in organic synthesis and is used in the production of a wide variety of organic compounds. Alkyl cyanides are versatile building blocks in organic chemistry and can be used to prepare a wide range of other compounds, such as carboxylic acids, amines, and amides.

One important application of the Stephen reaction is in the synthesis of pharmaceuticals. Many drugs contain a nitrile functional group, which can be prepared using the Stephen reaction. For example, the anti-cancer drug imatinib is prepared using a key intermediate that is synthesized using the Stephen reaction.

Conclusion

In conclusion, the Stephen reaction is a useful tool in organic synthesis for the preparation of alkyl cyanides from primary halides. It is named after the British chemist Henry Stephen, who first described the reaction in 1873. The reaction is typically carried out in the presence of a catalyst, such as copper(I) cyanide or cuprous cyanide, and proceeds via the formation of an intermediate that is attacked by the cyanide ion. The Stephen reaction has many applications in organic chemistry, particularly in the synthesis of pharmaceuticals and other organic compounds.

FAQ

What Is Stephen Reaction Class 12?

Alkyl nitriles on reduction with stannous chloride and hydrochloric acid in dry ether give corresponding imine hydrochlorides which on acid hydrolysis, give corresponding aldehydes. This reaction is known as Stephen’s reaction.

What Chapter Is Stephen’s Reaction In Class 12?

Preparation Method of Amines – Stephen’s Reaction | Class 12 Chemistry Chapter 13.

What Is The Stephen Method Of Chemistry?

Stephen aldehyde synthesis, a named reaction in chemistry, was invented by Henry Stephen (OBE/MBE). This reaction involves the preparation of aldehydes (R-CHO) from nitriles (R-CN) using tin(II) chloride (SnCl2), hydrochloric acid (HCl) and quenching the resulting iminium salt ([R-CH=NH2]+Cl−) with water (H2O).

What Is Stephen Deduction?

An alkyl or aryl cyanide dissolved in ether is reduced with stannous chloride and HCl to give aliphatic or aromatic aldehydes. The reaction proceeds by the formation of aldimine hydrochloride (present as stannichloride), which are not stable and hydrolyse to give aldehydes.

 

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