The Lumière–Barbier method is a method of
acetylating aromatic amine
In organic chemistry, an aromatic amine is an organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be a ...
s in aqueous solutions.
Illustrative is the acetylation of aniline. First aniline is dissolved in water using one equivalent of
hydrochloric acid
Hydrochloric acid, also known as muriatic acid or spirits of salt, is an aqueous solution of hydrogen chloride (HCl). It is a colorless solution with a distinctive pungency, pungent smell. It is classified as a acid strength, strong acid. It is ...
. This solution is subsequently treated, sequentially, with
acetic anhydride
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...
and aqueous sodium acetate. Aniline attacks acetic anhydride followed by deprotonation of the ammonium ion:
Acetate then acts as a leaving group:
The
acetanilide product is insoluble in water and can therefore be filtered off as crystals.
See also
*
Schotten–Baumann reaction
References
{{DEFAULTSORT:Lumiere-Barbier method
Organic reactions
Name reactions
Amide synthesis reactions