A textbook-perfect demonstration of functionalizing inert hydrocarbons through a logical sequence of strategic transformations. It’s a masterclass in synthetic "chess moves" that every aspiring chemist should internalize.
Deep Dive
Prerequisite Knowledge
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Deep Dive
The first step is free radical bromination. I said allyic by accidentAdded:
You propose the synthesis going from propane to acetone. That was exactly what a student that sent something into me was tasked with you starting only with propane going to a litany list of different products with acetone being one of them. This is going to be part of a series. Just stay put. So what do we got to do? We got to go from propane to acetone. So let's look. We didn't add any new carbons. There's still three carbons. Three carbons. However, now we have a ketone functionality. So let's work backwards. Remember ren retroynthesis is how it's going to get us there. So we have a ketone. Well, let's go backwards. Going to oxidize that the PCC from an alcohol.
Well, how did we get our alcohol?
We did a hydration of an alken. Now, depending on your professor, they might want you to write H2O H2 SO4. They might be okay with H3+.
I don't know. It's your professor, not mine. Only you can know. Just make sure you do whatever gets you the full credit. How do we get this propane?
Well, what if we had this two bromo propane and we did an elimination reaction? So, we'll just say base say sodium hydroxide and heat.
You can use any base you really want.
And that's going to get us to our prop.
Well, how do we get that? That's easy.
Br2 and light. Just a little bromination free radical. There you go. That's all you got to do to get from propane to acetone bromination.
Then you do an elimination reaction to form your alken. Hydration of the alken is going to give you marovnikov formation of that alcohol. oxidizes to the ketone.
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