The major products obtained upon treatment of tert-butyl methyl ether with excess HI gives Tertiary butyl iodide and Methanol.
CH3 – O – C – (CH3)3 + HI → CH3 – OH + (CH3)3– C-I
Tertiary butyl methyl ether + Hydrogen iodide → Methanol + Tertiary butyl iodide
Where iodine is attached to the 3 - C atom and -OH is attached to the -CH3 group. The reaction involves protonation of oxygen followed by an unimolecular nucleophilic substitution reaction ([tex]SN_{1}[/tex]).
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[tex]SN_{1}[/tex] reactions are nucleophilic substitutions, involving a nucleophile replacing a leaving group. However: [tex]SN_{1}[/tex] reactions are unimolecular: the rate of this reaction depends only on the concentration of one reactant.
[tex]SN_{1}[/tex] reactions occur mostly with tertiary alkyl halides due to steric reasons.
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