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

The correct option is D tert-butyl iodide and methyl alcohol

Tert-butyl methyl ether on treatment with hydrogen iodide in cold gives tert-butyl iodide and methyl alcohol.
$(C{H}_3{)}_{3}C-O-C{H}_3+HI\stackrel{cold}{\to }(C{H}_3{)}_{3}C-I+C{H}_3-OH$

When one of the alkyl groups is tertiary, then tertiary alkyl halide an lower alcohol is formed. (proceeds through the $S{N}^1$ mechanism since tertiary carbocation is most stable)

Option D is correct.