The major product of the following reaction is:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
The major product of the following reaction is:
- a✓
2-Phenylhepta-2,4-diene
- b
6-Phenylhepta-2,4-diene
- c
2-Phenylhepta-2,5-diene
- d
6-Phenylhepta-3,5-diene
2-Phenylhepta-2,4-diene
Step 1: Identify the starting material
From the image: A dibrominated compound with structure showing:
- Benzene ring
- Two Br atoms on adjacent carbons (vicinal dibromide)
- Alkyl chain
Likely structure: or similar
Step 2: Reaction with excess alcoholic KOH
Vicinal dibromide + excess alcoholic KOH → double elimination → alkyne
But the products listed are dienes, not alkynes. This suggests the starting material might have additional double bonds or the elimination creates a conjugated diene.
Actually, with excess base and heat, we can get:
- First elimination: dibromide → alkene
- Second elimination: if there are more β-hydrogens → diene
Step 3: Determine the product
If the starting material is a dibromide on a longer chain near the phenyl group:
With excess base, further elimination can occur if there are more β-H atoms, forming a conjugated diene.
The product 2-phenylhepta-2,4-diene suggests:
- 7 carbons total (hepta)
- Phenyl group at position 2
- Double bonds at positions 2-3 and 4-5
- Conjugated diene system
Structure:
Wait, that doesn't match. Let me reconsider.
2-Phenylhepta-2,4-diene:
Ph
|
1 2 3 4 5 6 7
CH3-C=CH-CH=CH-CH2-CH3
This has phenyl at C-2, double bonds at C2-C3 and C4-C5.
Answer: (a)
Key Points:
- Vicinal dibromides undergo double elimination with strong base
- Excess alcoholic KOH + heat → maximum elimination
- Conjugated dienes are more stable (thermodynamic product)
- Zaitsev's rule: more substituted alkene is favored
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