Question

Reaction of which among the following ether with $HI$ in cold leads to the formation of methyl alcohol?

• A. Ethyl methyl ether
• B. Methyl propyl ether
• C. Isopropyl methyl ether
• D. tert-butyl methyl ether

Answer 1

The correct option is D tert-butyl methyl ether

When tert-butyl methyl ether reacts with HI to form tert-butyl iodide and methanol.

$(C{H}_3{)}_{3}C-O-C{H}_3+HI\to (C{H}_3{)}_{3}C-I+C{H}_{3}OH$

The departure of leaving group $\left(C{H}_{3}OH\right)$ creates a more stable tert.carbocation, and the reaction follows $S{N}^1$ reaction mechanism.

So answer is D.