Consider the cleavage of tert-butyl methyl ether with concentrated . The reaction proceeds via an me — Alcohols Phenols and Ethers Chemistry Question
Question
Consider the cleavage of tert-butyl methyl ether with concentrated $HI$. The reaction proceeds via an $S_N1$ mechanism. Which of the following correctly describes the products formed?
Answer: B
💡 Solution & Explanation
When one of the alkyl groups is tertiary, cleavage shifts to $S_N1$ because the intermediate tertiary carbocation is highly stable. The $O-C(tert)$ bond breaks (rate-determining step), and the $I^-$ then attacks the stable carbocation, yielding tert-butyl iodide and methanol.
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