13 Nov addition of hobr to alkene
However, The pKa of HOBr is 8.7 (), much lower than those conditions, so it's not reasonable to make that analogy.Put another way, the base in those reactions is an alkene… For instance, the reaction between HBr and 1-butene that has just been distilled … The 'expected' product comes from analogy of addition of strong acids like HBr or acid (often sulfuric acid) catalyzed hydration. However, it’s an equilibrium situation. If your molecule contains both an alcohol and an alkene, I’d double-check to make sure that you can’t have intramolecular formation of a 5 or 6 membered ring from 1) addition of HBr across the double bond, and 2) attack of the OH on the resulting carbocation. The addition of HBr to alkenes proved to be a perplexing issue to chemists for quite a while. The result of this reaction varied from experiment to experiment, as it could not be controlled. Proton transfers to OH are generally faster than is addition to a double bond.
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