(CH3)3C - O - CH3 on reaction with HI gives (CH3)3C - I and CH3 - OH as the main products and not (CH3)3C - OH and CH3- I.

Question

Given reasons of the following :

(CH₃)₃C - O - CH₃ on reaction with HI gives (CH₃)₃C - I and CH₃ - OH as the main products and not (CH₃)₃C - OH and CH₃- I.

Answer 1

The reaction between (CH₃) C-O-CH, and HI follows S_N¹ mechanism. For an S_N¹ reaction, the formation of product is decided by the stability of the cabocation formed in the slowest step. As tert-  tertbutyl carbonium ion  formed after the cleavage of C-O bond in the slowest step is more stable than methyl carbonium ion therefore (CH₃)₃ C-I and CH₃OH are formed as main products.