1-methylcylopent-1-ene hydroboration
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Explanation:
hydroboration is Anti-Markovnikov
So 1-methylcyclohex-1-ene would give the alcohol on the least substituted site.
In the case of 1,2-dimethylcyclohexa-1,4-diene the double bonds are symmetrical.
In addition - in my opinion - the reactivity will be almost the same for the 2 double bonds. Hence the selectivity would be low.
This is certainly the case if we would consider the fact that a BH3 has 3 active hydrides. Hence it can react 3 times with a double bond.
In this case an intra-molecular reaction can and will take place so it will be very difficult to stop the reaction at the intermediate stage.
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