The major product obtained in the given reaction is:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
The major product obtained in the given reaction is:
- a
- b
- c✓
- d
Step 1: Identify the reaction
Ether with chloroalkyl side chain + (Lewis acid)
This is Friedel-Crafts alkylation (intramolecular)
Step 2: Mechanism overview
activates the C-Cl bond:
- Activation: (carbocation formation)
- Electrophilic attack: Carbocation attacks aromatic ring
- Ring closure: Intramolecular cyclization
Step 3: Common mistakes to avoid
Students often:
- Forget about ring size preferences (5 and 6-membered favored)
- Don't consider intramolecular vs intermolecular
- Miss rearrangements in carbocation intermediates
Step 4: Solving strategy
For intramolecular Friedel-Crafts:
- Identify the electrophilic center (where Cl is)
- Determine which aromatic ring can be attacked
- Check ring size formed (5 or 6-membered preferred)
- Consider regiochemistry (ortho/para to activating groups)
Answer: (c)
Key Points:
Friedel-Crafts alkylation:
- Requires Lewis acid catalyst (, )
- Forms C-C bond
- Can be intramolecular (ring closure)
- Carbocation rearrangements possible
Ring size preferences:
- 5-membered (most favored)
- 6-membered (favored)
- 3, 4, 7+ membered (less favored)
Limitations:
- Doesn't work with deactivated rings (NO₂, COOH)
- Multiple alkylation can occur
- Carbocation rearrangements
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