Question Details

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

Options

A

In step 2 of the reaction, the departure of leaving group (HO–CH3) creates less stable carbocation.

B

In step 2 of the reaction, the departure of leaving group (HO–CH3) creates more stable carbocation.

C

The reaction follows an SN1 mechanism.

D

The reaction follows SN2 mechanism.

Show Answer

Correct Answer :

Option B

In step 2 of the reaction, the departure of leaving group (HO–CH3) creates more stable carbocation.

Solution :

The correct option is: In step 2 of the reaction, the departure of leaving group (HO–CH3) creates more stable carbocation.

Let us understand the step-by-step mechanism of this reaction to explain why this option is correct.

Step 1: Protonation of the ether
In the first step, the oxygen atom of the ether methyl tert-butyl ether, (CH3)3C-O-CH3, gets protonated by the strong acid hydrogen iodide (HI) to form a protonated ether intermediate (oxonium ion):
(CH3)3C-O+(H)-CH3

Step 2: Departure of the leaving group and formation of the carbocation
Because one of the alkyl groups attached to the oxygen is a bulky tert-butyl group, the reaction proceeds via an SN1 mechanism rather than SN2.
In this step, the C - O bond between the tert-butyl carbon and the protonated oxygen breaks. The leaving group in this cleavage is neutral methanol (CH3OH).
The departure of this leaving group (CH3OH+- group) creates a highly stable tert-butyl carbocation, (CH3)3C+, which is a tertiary (3°) carbocation stabilized by nine hyperconjugative hydrogens and inductive effects.
If the bond had cleaved on the methyl side instead, it would have generated a highly unstable methyl carbocation (CH3+). Therefore, the reaction selectively forms the more stable carbocation.

Step 3: Nucleophilic attack
Finally, the halide nucleophile (iodide ion, I-) attacks the stable tert-butyl carbocation to yield tert-butyl iodide:
(CH3)3C++I-(CH3)3C-I
(Note: The question text mentions the formation of (CH3)3CCl as a typographical representation of the alkyl halide product, which corresponds to the tertiary butyl halide formed from this path.)

Thus, the reaction yields CH3OH and the tertiary alkyl halide because the departure of the leaving group in step 2 generates the more stable tertiary carbocation.

Unlock Our Free Library

Access expert-curated educational resources and study materials—completely free.

Ask AI Tutor
5 left
Q1 View Question & Options
AI Tutor is solving this question...
Reading question context & options...