Dat Destroyer # 83 Oc

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im not exactly sure because i dont see anything in my textbook about it, but i think if bromination is base catalyzed then the bromine will add anti-markovnikov, meaning the bromine will go the the carbon across the double bond with the most hydrogens. i know that if the case were peroxide as a solvent, then the addition would be anti-markovnikov with a bromine and hydroxyl group added across the double bond. i think this is similar to that problem. hope it helps.
 
This is just like reacting Br2 and H2O but it is methanol instead of H2O.
All I know is that the positively charged bromine is pulled in by the double bond first.
Then the OCH3 adds to the secondary carbocation instead of the Br- because the O is more electronegative.
 
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