[destofworlds]

I must provide a step by step mechanism that accounts for the reaction in the problem in the top bit of the image.  The bottom part is how far I got into the problem.

It seems clear that the OH group leaves and a carbocation is formed but it is on the wrong carbon.  As far as I know, it wouldn't shift the charge to the neighboring carbon, because they are both secondary.  So where do I go from there? 

Edit: I did have a hydrogen on the other oxygen on the acid but it got cut off when I scanned the image to my computer.  Sorry.

[wildfyr]

Such a carbocation is pretty unstable, where might there be electrons (perhaps in a double bond...) that can attack at that spot to close the ring?

[destofworlds]

I was  under the impression I needed to move the + charge first to Carbon 3, I had tried attacking with the far right phenol group but still couldn't figure out how to get the bond onto carbon 3 once I was there.

Also I apologise for my terrible sketches.

[wildfyr]

Ah, you are right, you do need to move it to C3. Why would it be favorable to move there? Just as a hint, such a move would be called a hydride shift if you arent familiar with it. Typically we do not draw this shift as an arrow push, its just shown that the + moves spontaneously to give a more stable carbocation (though I guess you could draw the arrow).



Once you move it then and attack with the double bond how might we reform aromaticity? Remember some kinda difficult reactions can happen because aromaticity is so heavily favored (24 kcal/mol!)

[destofworlds]

I'm honestly not sure why a shift would occur, both carbons are secondary and moving to a more substituted carbon it's usually why shifts occur.  Is the charge simply more stable on the benzylic carbon? 

I know the last part though, it's just the second half of an elimination reaction.

[clarkstill]

Is the charge simply more stable on the benzylic carbon? 

Much more stable (resonance stabilization)

[destofworlds]

Ok then!  Thanks a lot friends you've been a great help. Wish I had known about this place last fall for Organic I.