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JEE Main · 2024 · 27 Jan 2024 · Shift 2 · Alcohols Phenols and Ethers

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Major product formed in the following reaction is a mixture of:
  1. (A)(see structure) and (CH₃)₃CI
  2. (B)(see structure) and (CH₃)₃COH
  3. (C)(see structure) and (CH₃)₃COH
  4. (D)(see structure) and (see structure)
    Structure A
    A
    Structure B
    B
    ✓ Correct

Answer: (D)

Solution

The ether here is tert-butyl cyclohexyl ether, , reacting with excess HI. HI first protonates the ether oxygen. Cleavage of the C–O bond then proceeds preferentially on the tert-butyl side because it can generate the comparatively stable tertiary carbocation (an -type pathway), rather than forming the less stable secondary cyclohexyl cation. Iodide ion, a good nucleophile, combines with this tertiary carbocation to give tert-butyl iodide, , while the oxygen is left on the cyclohexyl fragment, which after protonation/deprotonation is released as cyclohexanol.

The major products are therefore cyclohexanol and tert-butyl iodide.

JEE Main · 2024 · 27 Jan 2024 · Shift 2 · Single correct option

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