Journal of Organic Chemistry p. 5356 - 5359 (1987)
Update date:2022-08-05
Topics:
Zucco, Cesar
Lima, Claudio F.
Rezende, Marcos C.
Vianna, Jose F.
Nome, Faruk
The basic hydrolysis of 2,2,2-trichloro-1-phenylethanone (1a), 2,2,2-trichloro-1-(p-methoxyphenyl)ethanone (1b), and 2,2,2-trichloro-1-(p-chlorophenyl)ethanone (1c) has been studied in the pH range 5.5-13.2.In all cases the reaction products were chloroform and the corresponding benzoate.The reaction is first order toward both the ethanone and hydroxide ion and proceeds via an addition-elimination-type mechanism.The initial addition step forms the corresponding ethanone hydrates, which, depending on the pH, will form the mono- and dianionic intermediates, the elimination of CCl3 from the mono- and/or dianionic species being the rate-limiting step of the reaction.
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