Question

$tert-butyl\, methyl$ ether on treatment with hydrogen iodide in cold gives

• A. tert-butyl iodide and methyl iodide
• B. tert-butyl alcohol and methyl alcohol
• C. tert-butyl alcohol and methyl iodide
• D. tert-butyl iodide and methyl alcohol

Answer 1

Answer: (D)

tert-butyl iodide and methyl alcohol

Answer 2

Tert-butyl methyl ether on treatment with hydrogen iodide in cold gives tert-butyl iodide and methyl alcohol.
$\left( CH _{3}\right)_{3} C - O - CH _{3}+ HI \ce{->[\text { cold }]}\left( CH _{3}\right)_{3} C - I + CH _{3}- OH$ When one of the alkyl groups is tertiary, then tertiary alkyl halide an lower alcohol is formed. (proceeds through the $SN ^{1}$ mechanism since tertiary carbocation is most stable)