Methyl-cyclobutane ether (?)

[Function]

Hi everyone

 

Asked is which product will be formed when this molecule reacts with hydrogen iodide:

 

 

And well... I simply can't answer this question. Conform Markovnikov, I'd say C...

But

• Is the name of the educt really "methyl-cyclobutane-ether"?
• Is it actually C?
• If yes, is this due to Markovnikov? Or something else?

Thanks!

 

F.

Edited December 19, 2014 by Function

[John Cuthber]

http://en.wikipedia.org/wiki/2-Methyltetrahydrofuran

[Altered State]

• It is known as 2-methyl tetrahydrofuran

I'd also say C...

...but not due to Markovnikov's rule, which only applies to electrophilic addition to alkenes. The reaction takes place though a mechanism where the Oxygen is protonated, and then the nucleophile (I-) will attack the most substituted carbon, so the most stable carbocation forms. It is something similar to the epoxides opening in acid media but in this case a REALLY strong acid is required for the molecule to open.

[Function]

 

• It is known as 2-methyl tetrahydrofuran
• I'd also say C...
• ...but not due to Markovnikov's rule, which only applies to electrophilic addition to alkenes. The reaction takes place though a mechanism where the Oxygen is protonated, and then the nucleophile (I-) will attack the most substituted carbon, so the most stable carbocation forms. It is something similar to the epoxides opening in acid media but in this case a REALLY strong acid is required for the molecule to open.

 

 

Thank you very much. Sounds a bit like Markovnikov, though, imo ^^

[Altered State]

 

Thank you very much. Sounds a bit like Markovnikov, though, imo ^^

 

Well, it might, because both are regioselectivity rules, but they are not the same and are not applied to the same scenarios.