Identify the major product in the following reaction.
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
Identify the major product in the following reaction.
- a
- b
- c
- d✓
Step 1: Identify the reaction
Cyclopentyl bromide with methyl substituent + in ethanol
Ethanol solvent with strong base → E2 elimination favored
Step 2: Determine structure
From the image: Cyclopentane ring with:
- Br at one position
- 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-Methylcyclopentene (internal double bond, more substituted)
- 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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