Acid Catalyzed Ether Cleavage

[w4nt2baDDS]

I was reviewing ochem reactions and when going over acid catalyzed ether cleavages I became confused about vinyl type ethers.

The image below shows two examples which were given to me but then I started to wonder how a vinyl type ether would react. Does anyone know which product it would form?

I'm guessing product C is correct... but from Example 2 I could see how A could be an option.

Or is C and A both wrong and something else actually forms?

---

Members don't see this ad.

 

[FeralisExtremum]

I would think product A is correct. With the figure drawn in your question, we can't do a substitution reaction on the sp2 hybridized carbon (regardless of if the ether is vinyl/aryl/phenyl), so we'd only be able to substitute on the other side. I'm not completely sure though.

 

[DAT Destroyer]

I was reviewing ochem reactions and when going over acid catalyzed ether cleavages I became confused about vinyl type ethers.

The image below shows two examples which were given to me but then I started to wonder how a vinyl type ether would react. Does anyone know which product it would form?

View attachment 190027

I'm guessing product C is correct... but from Example 2 I could see how A could be an option.

Or is C and A both wrong and something else actually forms?

First off, the acid protonates the O......attack the isopropyl group.....we get isopropyl bromide.....we all agree. Here is the tricky part.......we form the allylic alcohol. Ok...we add a H to C2 to yield the carbocation...... nicely resonance stabilized,,,,,,,,,the aldehyde forms!!!!! Think KETO_ENOL !!!! Thus we end up with isopropyl bromide and butanal.

Dr. Jim Romano

 

[w4nt2baDDS]

That's great! I see that, thanks a lot Dr. Ramano.

I forgot that enol's preferably tatautomerize into their carbonyl form.

This is essentially an acid catalyzed tatautomerism then?

 

[DAT Destroyer]

That's great! I see that, thanks a lot Dr. Ramano.

I forgot that enol's preferably tatautomerize into their carbonyl form.

This is essentially an acid catalyzed tatautomerism then?

Yes! Great job