In the following sequence of reaction, the major products B and C respectively are:
Haloalkanes & Haloarenes · Class 12 · JEE Main Previous Year Question
In the following sequence of reaction, the major products B and C respectively are:
- a✓
Option A
- b
Option B
- c
Option C
- d
Option D
Option A
Step 1: Reaction with Na/Et₂O (Wurtz coupling)
Cyclobutyl bromide + Na → Wurtz reaction → coupled product
Product A = Bicyclobutane (two cyclobutane rings joined)
Step 2: Grignard formation and deuterolysis
Product A + Mg in ether → Grignard reagent
Then reaction with (deuterium oxide):
This replaces the C-Mg bonds with C-D bonds.
Product B = Deuterated cyclobutane ()
Structure: Cyclobutane with D replacing H at the position where Br was originally.
Step 3: Reaction with CoF₂ (Swarts reaction)
Cyclobutyl bromide + → halogen exchange → fluoride
Product C = Cyclobutyl fluoride
Structure: Cyclobutane with F at the position where Br was.
Answer: (a)
Key Reactions:
- Wurtz coupling:
- Grignard + D₂O: (deuteration)
- Swarts reaction: (halogen exchange to fluoride)
Note: Deuterium (D or ²H) is used as a tracer isotope of hydrogen.
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