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Concept
Ketene
Summary
In organic chemistry, a ketene is an organic compound of the form , where R and R' are two arbitrary monovalent chemical groups (or two separate substitution sites in the same molecule). The name may also refer to the specific compound ethenone , the simplest ketene.
Although they are highly useful, most ketenes are unstable. When used as reagents in a chemical procedure, they are typically generated when needed, and consumed as soon as (or while) they are produced.
Ketenes were first studied as a class by Hermann Staudinger before 1905.
Ketenes were systematically investigated by Hermann Staudinger in 1905 in the form of diphenylketene (conversion of -chlorodiphenyl acetyl chloride with zinc). Staudinger was inspired by the first examples of reactive organic intermediates and stable radicals discovered by Moses Gomberg in 1900 (compounds with triphenylmethyl group).
Ketenes are highly electrophilic at the carbon atom bonded with the heteroatom, due to its sp character. Ketene can be formed with different heteroatom bonded to the sp carbon atom, such as O, S or Se, respectively named ketene, thioketene and selenoketene.
Ethenone, the simplest ketene, has different experimental lengths for each of the double bonds; the C=O bond is 1,160Å and the C=C bond is 1,314Å. The angle between the two H atoms is 121.5°, similar to the theoretically ideal angle formed in alkenes between sp2 carbon atom and H substituents.
Ketenes are unstable and cannot be stored. In the absence of nucleophiles with which to react, ethenone dimerises to give β-lactone, a cyclic ester. If the ketene is disubstituted, the dimerisation product is a substituted cyclobutadione. For monosubstituted ketenes, the dimerisation could afford either the ester or the diketone product.
Ethenone can be generated by pyrolysis (thermal cracking) of acetone:
CH3−CO−CH3 → CH2=C=O + CH4
This reaction is called the Schmidlin ketene synthesis.
Official source
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