Draw Irons
Draw the resonance structure of the most stable carbocation intermediate possible?
Draw the resonance structure of the most stable carbocation intermediate possible that results from step 2 of an electrophilic aromatic substitution reaction when tert-butylbenzene encounters bromine in the presence of iron(III) bromide.
Any help would be appreciated.
tert-butylbenzene is an activated molecule, and the t-butyl group is an ortho/para director. However, due to its size, it will direct predominantly para.
So the first step would be the double bond on the bottom-most carbon reaches out and grabs a bromine atom, which is only partially bonded to the second bromine atom, which is partially bonded to FeBr3; F3Br4 is kicked off as a leaving group. This leaves the positive charge on the carbon next to the bromine. That positive charge will obviously be delocalized around the ring; it will land in the para position from the bromine, which is on the carbon with t-butyl attached, and then it will land in the other ortho position to the bromine. When it is on the t-butyl carbon, it is most stable, because the t-butyl carbon group provides hyperconjugation to help stabilize the positive charge.
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