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: Identify the substrate
Tertiary carbon with:
- Cl (leaving group)
- Ester groups ()
Step 2: Reaction with NaOEt
Sodium ethoxide = Strong base
With tertiary halide → E2 elimination favored over
Step 3: Apply Zaitsev's rule
E2 elimination removes:
- Cl (leaving group)
- β-hydrogen
Forms more substituted alkene (Zaitsev product)
Step 4: Consider ester groups
Ester groups () are:
- Electron-withdrawing (inductive)
- Can stabilize adjacent negative charge
- Don't significantly affect elimination regiochemistry
Product: Alkene with ester substituents
Answer: (c)
Key Points:
E2 with polyfunctional molecules:
- Identify leaving group (Cl)
- Identify β-hydrogens
- Apply Zaitsev's rule (unless bulky base)
- Consider electron-withdrawing groups
Ester effects:
- Electron-withdrawing by induction
- Can participate in conjugation if adjacent to C=C
- α,β-Unsaturated esters are stable (conjugated)
Tertiary halides:
- Strongly favor elimination over substitution
- Even with good nucleophiles
- Steric hindrance blocks
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