Question

Explain results of oxidation of 4 bromoethylbenze? what would happen if there more then one alkyl group attached to benze ?

Answer 1

The oxidation of secondary benzylbromide, namely 2-bromoethyl)benzene, in refluxing acetonitrile/water revealed that the oxidation completed within 10 min; product analysis showed that the corresponding a-bromoketone
formed as a side product along with the major expected ketone in 85% yield (Eq. 1). When the reaction was conducted at room temperature, the reaction was found to be clean affording the ketone, i.e., 4-bromoacetophenone, primarily. Thus, secondary benzyl halides containing both electron-donating as well as electron-withdrawing groups were found to be oxidized; the substrate with electron-withdrawing group was found to undergo completion over a longer period and at reflux conditions