Question

Reaction of which among the following ethers with $HI$ in cold leads to 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

$H_{3}C-\stackrel{\stackrel{C{H}_3}{|}}{\underset{C{H}_3}{\underset{|}{C}}}-OC{H}_3\underset{cold}{\overset{HI}{\to }}{H}_{3}C-\stackrel{\stackrel{C{H}_3}{|}}{\underset{C{H}_3}{\underset{|}{C^{+}}}}\stackrel{HI}{\to }{H}_{3}C-\stackrel{\stackrel{C{H}_3}{|}}{\underset{C{H}_3}{\underset{|}{C{H}_3}}}+\underset{Methylalcohol}{C{H}_{3}OH}$

Reffer image. carbonation

Reaction of $HI$ with ether takes place by $S{N}^1$ mechanism.