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The Lumière–Barbier method is a method of acetylating aromatic amines in aqueous solutions.[1] An example of this is the acetylation of aniline.

First aniline is dissolved in water using one equivalent of hydrochloric acid:

Aqueous protonation of aniline.tiff

Then 1.2 equivalents of acetic anhydride is added followed by 1.2 equivalents of aqueous sodium acetate solution. Aniline attacks acetic anhydride followed by deprotonation of the ammonium ion:

Chem2.png

Acetate then acts as a leaving group:

Chem3.png

The acetanilide product is insoluble in water and can therefore be filtered off as crystals.

See alsoEdit

ReferencesEdit

  1. ^ Clayden; Greeves; Warren (2001). Organic chemistry. Oxford university press. p. 188. ISBN 978-0-19-850346-0.