Saturday, September 7, 2019

organic chemistry - Allylic Radicals Bromination Mechanism


For (a) (iii), how do you get the second product listed in the answers manual? I just can't visualize it.


What about (c) (i), why are there three resonance structures? If a hydrogen is taken away from a specific carbon of the initial molecule to have a radical, there is no way you can have three resonance structures.



Answer



The barrier to rotation in the allyl radical is low (~15-16 kcal/m) and it can undergo cis-trans isomerization.


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As to question (c)(i), you're right, there are only two resonance structures.



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What you show above with three resonance structures is the trimethylenemethane diradical, isobutene with 2 allylic hydrogens removed.


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