Hydrobromic acid reacts with alkenes to produce alkyl halides, and they also can perform o-demethylation on methyl ethers, producing the corresponding alcohol. On a compound that has both groups, which reaction will occur first?

  • $\begingroup$ My instinct is that you would not get any selectivity, but maybe some with database access can find specific examples. $\endgroup$ – Waylander Jan 31 at 9:42
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    $\begingroup$ To answer that kind of questions, you may want to find some experimental conditions and compare them. If one reaction needs to be carried out at rather high temperature but the other one doesn't, you can reasonably conclude that the high-temp reaction is much less favored than the other one. Also note that the demethylation reaction only works with aryl-methyl-ethers $\endgroup$ – SteffX Jan 31 at 12:44

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