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Account for the fact that treatment of terttert-butyl methyl ether with a limited amount of concentrated HI gives methanol and terttert-butyl iodide rather than methyl iodide and terttert-butyl alcohol.


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Tert-butyl methyl ether has a structure shown down below in the picture. When you look at it, oxygen has two lone pairs which means it can act like a base and deprotonate HI. After that step, iodide is formed along with protonated ether. C-O bond breaks and electrons hop on oxygen atom because the goal is to make methanol and tertiary carbocation. That way, iodide is excellent for nucleophilic attack at electrophilic carbon atom and tertiary halide is formed in this reaction.

Why aren't tertiary alcohol and methyl iodide formed? the reason for that lies in stability of carbocation. If, in any way, goal was to form tertiary alcohol, there would be methyl cation left - very unstable specie\textbf{very unstable specie} that's not favorable in any way. Also, reaction cannot follow SN1S_N1 reaction mechanism. It would rather undergo SN2S_N2 nucleophilic substitution if t-buthoxide was good leaving group.

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