Synthesis of Phthalic acid, Help Please!

If anyone could help, I've been at this for many hours and I can't figure out how! Thank-you!

Propose a mechanism for the synthesis of Phthalic acid. Taking into account that you have the following organic reactants and any inorganic reactants, gases and material that you need.

We have only learned the following reactions so I think I'll have to stick to these for the midterm: Electrophilic addition reactions (hydrogen halides, hydrogen bromide in the presence of peroxide, addition of halogen-Cl2 or Br2, Acid catalyzed addition of h20 and alcohols, oxymercuration-reduction, alkoxymercuration-reduction, hydroboration-oxidation, and addition of H - H2 and Pt/c etc. And some alkyne reactions: addition of halides, hydrogen bromide with peroxide, addition of halogens, water¬haydroboration-oxidation, addition of hydrogen and removal of a proton followed by alkylation.

I know how to add the OH group but I have to idea how to add a double bonded oxygen, I know how to get there from an alkyne but not an alkene and we haven't been given reactions to turn the alkene into an alkyne, just vice versa.

I imagine I could take away the H from the OH group which could leave me with a negative O but I don't know why it would make sense to do that without adding a halogen. Thank-you!

Edited February 21, 201510 yr by Alexandra_G