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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 .
A common type of organic acid anhydride is a carboxylic anhydride, where the parent acid is a carboxylic acid, the formula of the anhydride being (RC(O)) 2 O. Symmetrical acid anhydrides of this type are named by replacing the word acid in the name of the parent carboxylic acid by the word anhydride. [2] Thus, (CH 3 CO) 2 O is called acetic ...
In organic chemistry, an acetyl group is a functional group denoted by the chemical formula −COCH 3 and the structure −C(=O)−CH 3. It is sometimes represented by the symbol Ac [5] [6] (not to be confused with the element actinium). In IUPAC nomenclature, an acetyl group is called an ethanoyl group.
The enol form has C 2v symmetry, meaning the hydrogen atom is shared equally between the two oxygen atoms. [4] In the gas phase, the equilibrium constant, K keto→enol, is 11.7, favoring the enol form. The two tautomeric forms can be distinguished by NMR spectroscopy, IR spectroscopy and other methods. [5] [6]
It contains a double-bonded oxygen atom and an organyl group (R−C=O) or hydrogen in the case of formyl group (H−C=O). In organic chemistry, the acyl group (IUPAC name alkanoyl if the organyl group is alkyl) is usually derived from a carboxylic acid, in which case it has the formula R−C(=O)−, where R represents an organyl group or hydrogen.
As examples, a water molecule easily adds to ketene to give 1,1-dihydroxyethene and acetic anhydride is produced by the reaction of acetic acid with ketene. Reactions between diols (HO−R−OH) and bis-ketenes (O=C=CH−R'−CH=C=O) yield polyesters with a repeat unit of (−O−R−O−CO−R'−CO). Ethyl acetoacetate, an important starting ...
For example, it reacts with water to form acetic acid; [23] with acetic acid to form acetic anhydride; with ammonia and amines to form ethanamides; [24] and with dry hydrogen halides to form acetyl halides. [25] The formation of acetic acid likely occurs by an initial formation of 1,1-dihydroxyethene, which then tautomerizes to give the final ...
Acetyl hypochlorite is reported to be produced by the reaction of acetic anhydride and dichlorine monoxide at very low temperatures: [2]. Cl 2 O + (CH3CO) 2 O → 2CH 3 COOCl. The liquid can be distilled at reduced pressure, however it cannot be heated, as it violently decomposes at 100 °C to acetic anhydride, oxygen, and chlorine gas, and reacts with water and alcohols.