JEE Main · 2024 · Shift-IIhardHALO-056

In the above reaction product 'P' is:

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

Question

image In the above reaction product 'P' is:

Options
  1. a

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  2. b

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  3. c

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  4. d

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Correct Answerd

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Detailed Solution

Step 1: Identify the reaction type

Aryl bromide with \ceOCH3\ce{-OCH3} substituent + KCN (alcoholic)

This is nucleophilic aromatic substitution (SNArS_NAr)

Step 2: Understand SNArS_NAr requirements

Nucleophilic aromatic substitution requires:

  1. Electron-withdrawing groups (EWG) to activate the ring
  2. EWG should be ortho or para to the leaving group
  3. Strong nucleophile

Step 3: Analyze the substrate

Substituents:

  • Br: Leaving group
  • \ceOCH3\ce{-OCH3}: Electron-donating group (EDG) by resonance

Problem: \ceOCH3\ce{-OCH3} is an electron-donating group, which deactivates the ring toward nucleophilic substitution!

Aryl halides with only EDG substituents typically do not undergo SNArS_NAr under normal conditions.

Step 4: Consider alternative mechanism

With alcoholic KCN and heat, if the reaction occurs, it might be through:

  • Benzyne intermediate (elimination-addition mechanism)
  • Very harsh conditions needed

Or the question assumes the reaction proceeds despite unfavorable conditions.

Step 5: Determine product position

If SNArS_NAr occurs (or benzyne mechanism):

  • CN replaces Br
  • Position depends on directing effects

Given answer is (d), the CN is at a specific position relative to \ceOCH3\ce{-OCH3}.

For ortho-substituted product: \ceBrC6H4OCH3+CN>CNC6H4OCH3\ce{Br-C6H4-OCH3 + CN- -> CN-C6H4-OCH3}

With CN ortho to \ceOCH3\ce{-OCH3}.

Answer: (d)

Key Points:

  • SNArS_NAr requires electron-withdrawing groups (NO₂, CN, CHO, etc.)
  • Benzyne mechanism: Extreme conditions, elimination-addition
  • Directing effects: EDG (like OCH3) direct ortho/para in electrophilic substitution
  • Aryl halides are generally unreactive toward nucleophilic substitution without activation

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In the above reaction product 'P' is: (JEE Main 2024) | Canvas Classes