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Question 46

In the following reaction, 'B' is

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Screenshot 2026-05-25 170855

1. Protonation of the Alcohol

The lone pair of electrons on the oxygen atom of the secondary alcohol $$(-\text{OH}$$) attacks a hydronium ion $$(\text{H}^{+}$$).

The hydroxyl group is converted into an excellent leaving group, a protonated water molecule $$(-\text{OH}_{2}^{+}$$).

    2. Loss of Water (Carbocation Formation)

    The $$\text{C}-\text{O}$$ bond breaks, and water $$(\text{H}_2\text{O}$$) leaves.

    A secondary $$(2^{\circ }$$) carbocation is formed on the carbon chain adjacent to the bulky tert-butyl group.

      3. 1,2-Methyl $$(\text{CH}_{3}^{-}$$) Shift

      A secondary carbocation is relatively unstable. To gain stability, a methyl group from the adjacent tert-butyl group migrates with its electron pair (a 1,2-methyl shift) to the carbocation carbon.

      This rearranges the less stable $$2^{\circ }$$ carbocation into a highly stable tertiary $$(3^{\circ })$$ carbocation at the terminal branch.

        4. Intramolecular Cyclization (Ring Closure

        The $$\pi$$-electrons of the cyclohexene double bond act as an intramolecular nucleophile, attacking the newly formed tertiary carbocation.

        This nucleophilic attack closes the chain into a second 6-membered ring (forming a fused decalin system). A new tertiary carbocation is generated at the ring junction (bridgehead position).

          5. Deprotonation $$(-\text{H}^{+})$$ to Form the Major Product

          A weak base (such as water) removes a proton $$(\text{H}^{+})$$ from the adjacent carbon atom at the ring junction.

          Elimination of the proton forms a highly stable, tetrasubstituted double bond directly at the shared bridgehead position between the two fused 6-membered rings.

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