In the following given reaction 'A' is
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
In the following given reaction 'A' is
- a
- b
- c
- d✓
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 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:
- Protonation of the double bond forms a carbocation
- The cyclobutane ring (4-membered, highly strained) undergoes ring expansion to form a more stable 5-membered ring (cyclopentane)
- Br⁻ attacks the carbocation
The mechanism:
Step 4: Determine the product
After ring expansion and Br addition, the product is:
- Cyclopentane ring (5-membered, more stable than 4-membered)
- and 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
Practice this question with progress tracking
Want timed practice with adaptive difficulty? Solve this question (and hundreds more from Haloalkanes & Haloarenes) inside The Crucible, our adaptive practice platform.
More JEE Main Haloalkanes & Haloarenes PYQs
When sec-butylcyclohexane reacts with bromine in the presence of sunlight, the major product is:
Excess of isobutane on reaction with Br2 in presence of light at 125°C gives which one of the following, as the major product?
The major product of the following reaction is:
The products A and B in the following reactions, respectively are: A Ag-NO2 CH3-CH2-CH2-Br AgCN B
Propane molecule on chlorination under photochemical condition gives two di-chloro products, "x" and "y". Amongst "x" and "y", "x" is an optically active molecule. How many tri-chloro products…