[lostingeneral]

Hi,

I just received an assignment that I've been working on and I've hit something of a roadblock.

I'm asked to draw a mechanism for the following reaction:



This is my attempt thus far:



Since I can't see any way to get rid of that carbocation I think that I'm probably way off, so if anybody could point me in the right direction I'd really appreciate it.

Thanks.

Edit: I've also come up with this:



But I feel like this is not quite right, either.

[Vidya]

you are right in both the ways last step is the electrophilic substitution on the ring and + charge is delocalized within the ring .

so both of the steps are right

[orgopete]

They are the same reaction and you are using different resonance structures in the last step. The only difference is you did not show the hydrogen that become removed in the first.