[rburton]

I need to find a reaction to synthesize Acetophenone from benzene without using the Friedel-Crafts acylation, do you guys have any clue?

I just need to figure out the reactives, not the mechanism.


Thanks in advance!

Robert

[TheUnassuming]

I assume this is for a class?
What section are you currently covering?

[rburton]

Indeed, Alkenes, Alkynes and arenes.

[sjb]

Indeed, Alkenes, Alkynes and arenes.

DO you know how to convert any of these into a ketone?

[orgopete]

Hint, can you make the benzene ring into a better nucleophile, something that might add to an aldehyde or ketone?

[rburton]

I only know some particulars transformation of Alkenes into ketone, like Friedel-Crafts or Ozonolysis.

In order to make the benzene a better nucleophile, I guess it should loss some H, but I'm not sure how.

[orgopete]

Grignard?

[rburton]

What about with Acetic anhydride and Aluminium chloride, would that work?

[Dan]

What about with Acetic anhydride and Aluminium chloride, would that work?

That's Friedel-Crafts acylation.

[rburton]

Right! Would this Friedel-Crafts acylation works too if we had let's say a bromobenzene instead of a benzene, or in this case, there are other factors a take into account?

[Dan]

My point is you stated in your first post that you need a route without F-C acylation.

[rburton]

I didn't realize that was a F-C acylation.

[PL]

We can prepare acetophenone in vapour phase using zeolites as catalyst and aceticanhydride as acylating agent.

[kriggy]

That looks like a modification of friedel crafts.

What about Grignard reaction?