JEE Main · 2024 · Shift-IImediumHALO-048

Identify the major product in the following reaction.

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

Question

Identify the major product in the following reaction. image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerd

image

Detailed Solution

Step 1: Identify the reaction

Cyclopentyl bromide with methyl substituent + \ceOH\ce{OH-} in ethanol

Ethanol solvent with strong base → E2 elimination favored

Step 2: Determine structure

From the image: Cyclopentane ring with:

  • Br at one position
  • \ceCH3\ce{CH3} at adjacent or nearby position

Likely structure: 1-bromo-2-methylcyclopentane or similar

Step 3: Apply E2 elimination

E2 elimination requires:

  • Anti-periplanar geometry (H and Br on opposite sides)
  • Removal of β-hydrogen

Zaitsev's rule: More substituted alkene is favored

For 1-bromo-2-methylcyclopentane:

Elimination can give:

  1. 1-Methylcyclopentene (internal double bond, more substituted)
  2. Methylenecyclopentane (exocyclic double bond, less substituted)

By Zaitsev's rule, the more substituted alkene is major product:

1-Methylcyclopentene (double bond in the ring, with methyl substituent)

Answer: (d)

Key Points:

  • E2 elimination: Strong base, good leaving group, β-hydrogen
  • Zaitsev's rule: More substituted alkene is thermodynamically favored
  • Hofmann product: Less substituted alkene (with bulky base or poor leaving group)
  • Cyclic systems: Internal double bond usually more stable than exocyclic

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Identify the major product in the following reaction. (JEE Main 2024) | Canvas Classes