Lumiere-Barbier method

As an example, let us look at a method for acetylating aromatic amines in aqueous solution. This reaction has a special name—the Lumiere-Barbier method. We shall consider the acetylation of aniline PhNH2 (a basic aromatic amine) using acetic anhydride. The procedure for this reaction is as follows. 

In ihe method for acetylating aromatic amines described in Chapter 8, p. 000 (the Lumiere-Barbier method) the amine was dissolved in aqueous HCl. Using 1M amine, p.fCa 4.6, and 1M HC1, piCj -7, what will be the approximate equilibrium constant in the reaction ... 

Of course, electron-withdrawing groups on the benzene ring will affect the availability of the lone pair. For example, the pKgH of p-nitro aniline is only 1.11. This explains why certain aromatic amines (for example, nitroanilines and dibromoanilines) can t be acetylated using the Lumiere-Barbier method (p. 188). 

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See also in sourсe #XX -- [ ]

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