JEE Main · 2019 · Shift-IhardHC-022

The major product of the following reaction is:

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

The major product of the following reaction is: image

Options
  1. a

    Compound a

  2. b

    Compound b

  3. c

    Compound c

  4. d

    Compound d

Correct Answerc

Compound c

Detailed Solution

Step 1: Identify the substrate and reaction type

The starting material has:

  • An aromatic ring with \ceOCH3\ce{-OCH3} (methoxy) substituent
  • A side chain ending in \ceCH2Cl\ce{-CH2Cl} (alkyl chloride) — 3 carbons from the ring

With \ceAlCl3\ce{AlCl3} (Lewis acid), this undergoes intramolecular Friedel-Crafts alkylation.

image Many books mark option d as correct answer but in my opinion that's incorrect. Primary carbocations (11^\circ) are too unstable to exist as free intermediates. In a Friedel-Crafts reaction with a primary alkyl halide and AlCl3AlCl_3, the reaction proceeds via an SN2\text{S}_\text{N}2-like displacement or a tight ion-pair.

By the time the AlCl3AlCl_3 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 26 kJ/mol26 \text{ kJ/mol} 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. image

Key Points to Remember:

  • Intramolecular FC alkylation prefers 6-membered ring formation
  • \ceOCH3\ce{-OCH3} activates ortho/para positions for electrophilic attack
  • The most stable carbocation determines the ring closure site

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