Question Details

Products are

Options

A

B

C

D

Correct Answer :

Cyclohexanol and tert-butyl iodide

Solution :

The correct option is the one showing cyclohexanol and tert-butyl iodide (represented as a cyclohexane ring with a hydroxyl group, and (CH3)3C-I).

Step-by-step Explanation:

1. Understanding the Reactants:
The starting material shown in the question is cyclohexyl tert-butyl ether, which is an unsymmetrical ether. In this molecule, the oxygen atom is connected to:
- A secondary alkyl group (cyclohexyl ring)
- A tertiary alkyl group (tert-butyl group, -C(CH3)3)

2. Protonation of the Ether:
When treated with a strong acid like cold hydroiodic acid (HI), the lone pairs on the ether oxygen atom abstract a proton (H+) from HI to form a protonated ether (oxonium ion intermediate):

Ether+H+Protonated Ether (Oxonium ion)

3. Determining the Mechanism (SN1 vs SN2):
- Generally, the reaction of unsymmetrical ethers with cold HI occurs via an SN2 pathway, where the iodide nucleophile (I-) attacks the less sterically hindered carbon atom.
- However, if one of the alkyl groups attached to the ether oxygen is a tertiary alkyl group (such as the tert-butyl group), the reaction mechanism shifts to an SN1 pathway.
- This shift occurs because the tertiary C-O bond can easily cleave to generate an exceptionally stable tert-butyl carbocation ((CH3)3C+).

4. Cleavage and Carbocation Formation:
The protonated ether undergoes heterolytic cleavage at the C-O bond connecting the oxygen and the tert-butyl group:

Protonated EtherCyclohexanol+(CH3)3C+

This leaves behind cyclohexanol as the alcohol product.

5. Nucleophilic Attack:
The remaining iodide ion (I-) rapidly attacks the highly reactive tert-butyl carbocation to form the halide product, tert-butyl iodide:

(CH3)3C++I-(CH3)3C-I

Therefore, the final products of this reaction are cyclohexanol and tert-butyl iodide.

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