Wurtz–Fittig reaction

Wurtz–Fittig Reaction

Error creating thumbnail:

Schematic representation of the Wurtz–Fittig reaction.

The Wurtz–Fittig reaction is an important organic chemistry reaction used to synthesize alkyl aryl ethers and alkyl aryl ketones. It is a modification of the Wurtz reaction, which is used to couple two alkyl halides to form a hydrocarbon. The Wurtz–Fittig reaction involves the coupling of an aryl halide with an alkyl halide in the presence of sodium metal.

Mechanism

The mechanism of the Wurtz–Fittig reaction involves the formation of a radical intermediate. Initially, sodium metal donates an electron to the aryl halide, generating an aryl radical and a sodium halide salt. The aryl radical then reacts with the alkyl halide to form a new carbon-carbon bond, resulting in the formation of the desired product.

Applications

The Wurtz–Fittig reaction is used in the synthesis of various organic compounds, particularly in the preparation of alkyl aryl ethers and alkyl aryl ketones. These compounds are valuable in the production of pharmaceuticals, fragrances, and polymers.

Limitations

One of the main limitations of the Wurtz–Fittig reaction is the formation of side products due to competing reactions, such as the formation of biphenyl from the coupling of two aryl radicals. Additionally, the reaction is sensitive to the presence of moisture and oxygen, which can lead to the formation of unwanted byproducts.

Related Pages

• Wurtz reaction
• Friedel–Crafts reaction
• Grignard reaction