JEE Main · 2019 · Shift-IImediumHALO-111

The major product obtained in the given reaction is:

Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question

Question

The major product obtained in the given reaction is: image

Options
  1. a

    image

  2. b

    image

  3. c

    image

  4. d

    image

Correct Answerc

image

Detailed Solution

Step 1: Identify the reaction

Ether with chloroalkyl side chain + \ceAlCl3\ce{AlCl3} (Lewis acid)

This is Friedel-Crafts alkylation (intramolecular)

Step 2: Mechanism overview

\ceAlCl3\ce{AlCl3} activates the C-Cl bond:

  1. Activation: \ceRCl+AlCl3>R++AlCl4\ce{R-Cl + AlCl3 -> R+ + AlCl4-} (carbocation formation)
  2. Electrophilic attack: Carbocation attacks aromatic ring
  3. 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:

  1. Identify the electrophilic center (where Cl is)
  2. Determine which aromatic ring can be attacked
  3. Check ring size formed (5 or 6-membered preferred)
  4. Consider regiochemistry (ortho/para to activating groups)

Answer: (c)

Key Points:

Friedel-Crafts alkylation:

  • Requires Lewis acid catalyst (\ceAlCl3\ce{AlCl3}, \ceFeCl3\ce{FeCl3})
  • 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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The major product obtained in the given reaction is: (JEE Main 2019) | Canvas Classes