The Lumière–Barbier method is a method of
acetylating aromatic amine
In organic chemistry, an aromatic amine is an organic compound consisting of an aromatic ring attached to an amine. It is a broad class of compounds that encompasses aniline
Aniline is an organic compound with the formula C6 H5 NH2. Consi ...
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, is an aqueous solution of hydrogen chloride. It is a colorless solution with a distinctive pungent smell. It is classified as a strong acid
Acid strength is the tendency of an acid, symbol ...
. This solution is subsequently treated, sequentially, with
acetic anhydride and aqueous sodium acetate. Aniline attacks acetic anhydride followed by deprotonation of the ammonium ion:
Acetate then acts as a leaving group:
The
acetanilide
Acetanilide is an odourless solid chemical of leaf or flake-like appearance. It is also known as ''N''-phenylacetamide, acetanil, or acetanilid, and was formerly known by the trade name Antifebrin.
Preparation and properties
Acetanilide can be ...
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