Tuesday, December 10, 2019

organic chemistry - What determines the high degree of selectivity in free radical brominations?



In my organic chemistry class, we were asked what determines the relatively high degree of selectivity in the reaction of a bromine radical with primary, secondary, and tertiary C–H bonds.


I said it is the overall free energy of the reaction because according to Hammond's postulate, endothermic (endergonic) reactions have transition states closely resembling the product side, making the difference between primary, secondary, and tertiary radicals more important in the transition state.


Would this logic be wrong?




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