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
- b
- c
- d✓
Step 1: First reaction - Free radical chlorination
Toluene + /light:
Free radical substitution at benzylic position (most reactive)
Product: Benzyl chloride
Step 2: Second reaction - Hydrolysis
Benzyl chloride + /heat:
substitution (benzylic position is very reactive)
Product: Benzyl alcohol
Answer: (a) Benzyl alcohol ()
Key Reactions:
Free radical halogenation:
- Requires light or heat
- Selectivity: Benzylic > Allylic > 3° > 2° > 1°
- Benzylic C-H bonds are weakest (most reactive)
Benzylic reactivity:
- Benzylic radicals are stabilized by resonance
- Benzylic carbocations are stabilized by resonance
- Both and are fast at benzylic position
Common mistake:
- Thinking Cl₂/light will chlorinate the ring (that needs Lewis acid)
- Free radical conditions favor side-chain substitution
Alternative products with excess Cl₂:
- (benzal chloride)
- (benzotrichloride)
But with 1 equiv Cl₂, benzyl chloride is major product.
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