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Illustrative is the acetylation of aniline. First aniline is dissolved in water using one equivalent of hydrochloric acid. 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:
Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH 3 CO) 2 O. Commonly abbreviated Ac 2 O , it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis .
Aniline (from Portuguese anil 'indigo shrub', and -ine indicating a derived substance) [6] is an organic compound with the formula C 6 H 5 NH 2. Consisting of a phenyl group ( −C 6 H 5 ) attached to an amino group ( −NH 2 ), aniline is the simplest aromatic amine .
Acetic anhydride. This reagent is common in the laboratory; its use cogenerates acetic acid. [7] [10] Acetyl chloride. This reagent is also common in the laboratory, but its use cogenerates hydrogen chloride, which can be undesirable. [8] Ketene. At one time acetic anhydride was prepared by the reaction of ketene with acetic acid: [11]
Hippuric acid, the benzamide derivative of glycine, cyclizes in the presence of acetic anhydride, condensing to give 2-phenyl-oxazolone. [3] This intermediate also has two acidic protons and reacts with benzaldehyde, acetic anhydride and sodium acetate to a so-called azlactone. This compound on reduction gives access to phenylalanine. [4]
acylation of a benzylamine with acetyl chloride (acetic anhydride is an alternative) In the Fischer peptide synthesis (Emil Fischer, 1903), [6] an α-chloro acid chloride is condensed with the ester of an amino acid. The ester is then hydrolyzed and the acid converted to the acid chloride, enabling the extension of the peptide chain by another ...
The following figure shows the reaction mechanism: [2] Reaktionsmechanismus Albright-Goldman-Oxidation. First, dimethyl sulfoxide (1) reacts with acetic anhydride to form a sulfonium ion. It reacts with the primary alcohol in an addition reaction. Furthermore, acetic acid is cleaved, so that intermediate 2 is formed. The latter reacts upon ...
The general mechanism for primary alkyl halides is shown below. [8] Mechanism of Friedel–Crafts alkylation. For primary (and possibly secondary) alkyl halides, a carbocation-like complex with the Lewis acid, [R (+)---(X---MX n) (–)] is more likely to be involved, rather than a free carbocation.