Function Posted December 19, 2014 Posted December 19, 2014 (edited) 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 Posted December 20, 2014 Posted December 20, 2014 http://en.wikipedia.org/wiki/2-Methyltetrahydrofuran
Altered State Posted December 20, 2014 Posted December 20, 2014 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. 1
Function Posted December 20, 2014 Author Posted December 20, 2014 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 Posted December 22, 2014 Posted December 22, 2014 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.
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