The reaction of tert-butyl methyl ether with | vedclass

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(D) When $tert$-butyl methyl ether reacts with $HI$,it undergoes protonation of the ether oxygen followed by cleavage. Since the $tert$-butyl group ca

Vedclass · Accepted Answer

$tert$-butyl iodide and methanol

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(D) When $tert$-butyl methyl ether reacts with $HI$,it undergoes protonation of the ether oxygen followed by cleavage. Since the $tert$-butyl group can form a stable tertiary carbocation,the reaction proceeds via an $S_N1$ mechanism. The iodide ion $(I^-)$ attacks the $tert$-butyl carbocation to form $tert$-butyl iodide,while the methanol $(CH_3OH)$ is formed from the methyl group. The reaction is: $(CH_3)_3C-O-CH_3 + HI \rightarrow (CH_3)_3C-I + CH_3OH$.

The reaction of $tert$-butyl methyl ether with one equivalent of $HI$ gives:

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