In the above reaction product 'P' is:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
In the above reaction product 'P' is:
- a
- b
- c
- d✓
Step 1: Identify the reaction type
Aryl bromide with substituent + KCN (alcoholic)
This is nucleophilic aromatic substitution ()
Step 2: Understand requirements
Nucleophilic aromatic substitution requires:
- Electron-withdrawing groups (EWG) to activate the ring
- EWG should be ortho or para to the leaving group
- Strong nucleophile
Step 3: Analyze the substrate
Substituents:
- Br: Leaving group
- : Electron-donating group (EDG) by resonance
Problem: is an electron-donating group, which deactivates the ring toward nucleophilic substitution!
Aryl halides with only EDG substituents typically do not undergo 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 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 .
For ortho-substituted product:
With CN ortho to .
Answer: (d)
Key Points:
- 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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