JEE Main · 2023 · Shift-IhardHALO-010

In the following given reaction 'A' is

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

In the following given reaction 'A' is image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerd

image

Detailed Solution

Step 1: Identify the starting compound

The structure shows a cyclobutane ring with an exocyclic double bond and a methyl group:

    CH3
     |
     C==CH2
    / \
   |   |
    \_/

This is methylenecyclobutane with structure: cyclobutane with \ce=CH2\ce{=CH2} group.

Step 2: Understand HBr addition

HBr adds to alkenes following Markovnikov's rule: H goes to the carbon with more H atoms, Br goes to the more substituted carbon.

But with strained rings like cyclobutane, ring expansion can occur to relieve ring strain.

Step 3: Ring expansion mechanism

When HBr adds:

  1. Protonation of the double bond forms a carbocation
  2. The cyclobutane ring (4-membered, highly strained) undergoes ring expansion to form a more stable 5-membered ring (cyclopentane)
  3. Br⁻ attacks the carbocation

The mechanism: \cemethylenecyclobutane+H+>carbocation(withringexpansion)>cyclopentanederivative\ce{methylenecyclobutane + H+ -> carbocation (with ring expansion) -> cyclopentane derivative}

Step 4: Determine the product

After ring expansion and Br addition, the product is:

  • Cyclopentane ring (5-membered, more stable than 4-membered)
  • \ceBr\ce{Br} and \ceCH3\ce{CH3} on adjacent carbons

Looking at option (d): This describes a cyclopentane with substituents, which matches ring expansion.

Answer: (d)

Key Points:

  • Small rings (3, 4-membered) are strained and undergo ring expansion
  • Ring expansion: 4-membered → 5-membered (more stable)
  • Carbocation rearrangements favor more stable products

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In the following given reaction 'A' is (JEE Main 2023) | Canvas Classes