i think a triple bond should have been there in the question instead of the double bond...that is the trick in the question !
1st is hydroboration oxidation
2nd is oxymercuration-demercuration
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Why should a triple bond have been there..?
HBO should go on normally, except when oxidation takes place. In oxymercuration, a mercurinium ion could form on C=O as well...
actually we would have got an entirely different product if that would have been a triple bond...in this case it seems normal....what is the problem then...simple mechanisms,,thats all!
in hbo the oh gets attached to that carbon which is less sterically hindered
and in omdm the oh gets attached to dat carbon on which positive charge is more stable
these can be proved by mechanism
Check the inductive effect in case of OMDM.
From which side will the ring break in the transition state?
same product occurs due to the positive charge on the carbon in the carbonyl group attached nearby !! thats all,i think !