Wurtz–Fittig reaction
In the Wurtz synthesis is a name reaction in organic chemistry. It represents one of Rudolph Fittig 1863 extended form of Wurtzschen synthesis and is used in the synthesis of alkylated aromatics. However, since the yields due to side reactions are caused mostly low, the Wurtz reaction has no particular synthetic importance.
Overview reaction
In the reaction, a haloalkane and a halogen compound with an alkali metal in an inert solvent is converted to an alkylated aromatics.
Mechanism
The reaction has strong analogies to Wurtzschen synthesis. Rather than chloride or bromide, other halides can be bound.
In a first step, the more reactive alkyl halide in comparison to the aryl halide of sodium is reduced to the carbanion. This can react in a nucleophilic substitution reaction with the aryl halide to give the corresponding alkylated aromatics.
Side reactions
Driving force of the process is the formation of precipitating out of solution sodium halide, since it has a high lattice energy. Adverse reactions are varied and reduce yields significantly. The following responses are possible, for example:
- Elimination reactions
- Coupling reaction
- Coupling reaction
See also
Wurtz synthesis
Fittig reaction
Friedel -Crafts alkylation
Ullmann reaction