Abstract
Abstract Bromobenzene is obtained in a 56% yield when an acetic acid solution of peroxyacetic acid is slowly added to an acetic acid solution of bromine, benzene and a catalytic amount of sulfuric acid. The rate of the consumption of peroxyacetic acid has been expressed as v=k2 [CH3CO3H] [Br2], where k2 is independent of the concentration of benzene and of the acidity of solution. However, the rate of the formation of bromobenzene is accelerated by sulfuric acid and a more effective use of the attacking species is possible. A mechanism has been suggested which involves the ratedetermining formation of bromine monoxide or acetyl hypobromite, followed by its rapid attack on benzene. The rate is slower with benzene substituted with electron-attracting groups. Some evidence for the formation of acetyl hypobromite has been obtained by ultraviolet spectrophotometry.
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