Question:medium

In the reaction, (CH3)3C − O − CH3 + HI → Products, CH3OH and (CH3)3CCl are the products and not CH3I and (CH3)3COH. It is because

Updated On: Jan 16, 2026
  • (A) In step 2 of the reaction, the departure of leaving group (HO–CH3) creates less stable carbocation

  • (B) The reaction follows an SN1 mechanism

     

  • (C) In step 2 of the reaction, the departure of leaving group (HO–CH3) creates more stable carbonation

  • (D) The reaction follows SN2 mechanism
Show Solution

The Correct Option is B

Solution and Explanation

The reaction of tert-butyl methyl ether with hydroiodic acid yields methanol and tert-butyl chloride, not methyl iodide and tert-butyl alcohol, because it proceeds via an SN1 mechanism. SN1 reactions involve a carbocation intermediate in their rate-determining step. The stability of this carbocation is paramount. In this instance, the tert-butyl carbocation ((CH3)3C+) is more stable than a methyl carbocation. Consequently, the subsequent reaction steps favor the formation of methanol and tert-butyl chloride. This carbocation stability dictates the reaction pathway, leading to the observed products over alternatives like methyl iodide and tert-butyl alcohol.

Therefore, the accurate explanation is: (B) The reaction proceeds via an SN1 mechanism.

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