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Question
Write the mechanism of the reaction of HI with methoxymethane.
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Solution
The reaction between methoxymethane and HI is:
\[\ce{CH3 - O - CH3 + HI -> CH3I + CH3OH}\]
Generation of oxonium ion (Step 1): Protonation of the ether molecule.
Nucleophilic attack on oxonium ion (Step 2):
If excess HI is used, the methanol formed above reacts with HI to form methyl iodide.
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