Reacting anisole with concentrated H2SO4

[tellmesomething]

Homework Statement

Can someone explain to me how this mechanism works, and why wouldn't h+ be generated and attack the ortho para electron rich sites in anisole? It seems it breaks as OH- and So3H+ but mostly reactions we had done before had H+ breaking, how do I decide how the acid breaks? ( I thought since H is attached to O its very acidic and would always give us a supply of hydronium ions)

Relevant Equations

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[mjc123]

What mechanism?

 

[tellmesomething]

What mechanism?

I have stated in the title. Reacting anisole with conc. H2so4..

 

[Mayhem]

Not sure what you mean. H2SO4 doesnt decompose when acting as a normal acid; it deprotonates completely into one equivalent and partially into a second equivalent.

The cleavage of ethers with strong acids is known, but usually a halogen acid (HCl, HBr, HI) most be used to generate a halogenated product (halomethane in the case of anisole). H2SO4 wont hydrate aromatic rings like it does alkenes since aromaticity changes the reactivity and nature of the double bonds.

Your question is a bit unclear so I hope this answers it.

 

[ketoenol]

I assume you're doing an aromatic sulfonation? If you google "aromatic sulfonation mechanism" you'll get various diagrams. There's different ways of depicting it; I think the most clear to me is just to consider sulfur trioxide as your electrophile (sulfuric acid, especially when concentrated, can for some purposes be thought of as a solution of sulfur trioxide)