# Best reagent to convert 4-chloro-4H-pyran into an aromatic compound

My question:

My attempt: (I am not really good at mechanisms, so a little help would be good. Thank-you)

I do not know what kind of reactions these will give.

What kind of reagent would promote this process, i.e., a halide leaving? A Lewis acid, such as $$\ce{AlCl3}$$ could promote this in two ways. First, it could interact with the chloride in the starting material, building up positive charge on the chloride, making it a better leaving group. Secondly, the Lewis acid can coordinate the chloride on the product side, preventing it from attacking the pyrylium ion.