The major product of the following reaction is:
Hydrocarbons · Class 11 · JEE Main Previous Year Question
The major product of the following reaction is:
- a
Compound a
- b
Compound b
- c✓
Compound c
- d
Compound d
Compound c
Step 1: Identify the substrate and reaction type
The starting material has:
- An aromatic ring with (methoxy) substituent
- A side chain ending in (alkyl chloride) — 3 carbons from the ring
With (Lewis acid), this undergoes intramolecular Friedel-Crafts alkylation.
Many books mark option d as correct answer but in my opinion that's incorrect.
Primary carbocations () are too unstable to exist as free intermediates. In a Friedel-Crafts reaction with a primary alkyl halide and , the reaction proceeds via an -like displacement or a tight ion-pair.
By the time the pulls the chloride away enough to allow for a hydride shift, the benzene ring (which is part of the same molecule) is already positioned to attack.
Ring Strain: A 6-membered cyclohexane-like ring has almost zero ring strain, whereas a 5-membered cyclopentane-like ring has approximately of strain.
The Distance Factor: While 5-membered rings often form faster (entropy), 6-membered rings are thermodynamically more stable. In Friedel-Crafts alkylations, which are often reversible or governed by the stability of the transitioning complex, the 6-membered path is highly competitive.
Key Points to Remember:
- Intramolecular FC alkylation prefers 6-membered ring formation
- activates ortho/para positions for electrophilic attack
- The most stable carbocation determines the ring closure site
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