Beginning with the Addition of Gaseous Hydrogen Chloride to the Given Nitrile, the Stephen Reaction Mechanism occurs. In honor of its creator Henry Stephen, the reaction is called the Stephen aldehyde synthesis. The reaction entails converting nitriles into aldehydes using tin(II) chloride and hydrochloric acid, followed by quenching the resultant iminium salt in water. Another useful byproduct of this process is ammonium chloride.
Stephen Reaction
The organic redox process known as the Stephen reaction is utilised to create aldehydes. It is sometimes referred to as Stephen Aldehyde Synthesis or Stephen Reduction. Henry Stephen, an English chemist, created the Stephen Reaction, giving it its name. It is a crucial naming reaction in organic chemistry as well. With the aid of hydrochloric acid, nitriles are reduced to imines with tin chloride in an organic redox process that, upon hydrolysis, yields aldehydes. We also receive ammonia and ammonium chloride as a side product. Methyl nitrite interacts with tin chloride and hydrochloric acid to produce iminium salt. Aldehyde is formed after further quenching iminium salt with water. We also produce a small amount of ammonium chloride or ammonia as a byproduct of this reaction. Because the created iminium salt is produced as an intermediate product, more quenching is necessary because it is not stable.
Stephen Reaction Mechanism
Other names for the Stephen process include the Stephen aldehyde synthesis and the Stephen reduction reaction. Henry Stephen, a chemist, made the initial discovery. The final result of this organic redox reaction is an aldehyde. The Stephen reduction reaction is another name for the process.
Steps required for Stephen Reaction Mechanism are:
Step1
In the first phase of the Stephen reaction, hydrogen chloride fumes are passed across nitrile, causing associated salt to form.
Step2
In the second stage, salt is created by a single electron transfer in stannous(ll) chloride.
Step3
In this phase, the salt that was obtained is precipitated. Aldimine tin chloride precipitates as the salt.
Step4
The salt obtained in the previous stage is hydrolyzed to produce amide in the last phase. Aldehyde is the final outcome of this. Aldehyde is the final product of the Stephen reaction process. The key thing to keep in mind while using aliphatic nitrile is that aromatic nitrile is more effective. The production of tin chloride as a salt is enhanced by the use of replacements that are added to increase electron density. It is also possible to encourage the creation of compounds that remove electrons, such as amide chloride.
Stephen Reduction Reaction
Methyl nitrile interacts with hydrochloric acid and tin chloride to form the iminium salt in the Stephen reduction reaction. This iminium salt is further cooled with water to produce aldehyde. In this reaction, we also produce various byproducts like ammonium chloride or ammonia. The reaction results in the production of either aromatic or aliphatic aldehydes. Further quenching is needed in the Stephen reduction reaction because the iminium salt formed as intermediate products is not stable.
Examples of Stephen Reaction
Acetaldehyde is produced from acetonitrile.
The conversion of benzonitrile to benzaldehyde.
Stephen Reaction Explanation
The supplied nitrile is mixed with gaseous hydrogen chloride (HCl), which reacts to produce the matching salt. This salt is reduced by a single electron transfer from tin(II) chloride. Tin (IV) tetrachloride and amine are produced after further reduction with HCl. Shortly after, aldimine tin chloride precipitates out of the salt made in step 2. Aldimine tin chloride is hydrolyzed to produce an amide. This amide is converted into the necessary aldehyde. Ammonium chloride is also created during this process.
Conclusion
Alkyl cyanides are utilised in the Stephens reduction procedure to create aldehydes. The terms Stephen Reaction, Stephen Reduction, and Stephen Aldehyde Synthesis are also used. Methyl nitrite interacts with tin chloride and hydrochloric acid to produce iminium salt. Aldehyde is formed after further quenching iminium salt with water. Acetaldehyde is produced from acetonitrile. the conversion of benzonitrile to benzaldehyde. Aldimine tin chloride will develop more readily when substitutes used to increase electron density are also applied. An electron-withdrawing compound promotes the formation of amide chloride.