Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of light?
Hydrocarbons · Class 11 · JEE Main Previous Year Question
Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of light?
- a
-hydrogen
- b✓
-hydrogen
- c
-hydrogen
- d
-hydrogen
-hydrogen
Step 1: Identify compound E and its hydrogens
Compound E: (but-1-ene)
Labeling positions relative to the double bond:
- C1 (): vinyl position
- C2 (): vinyl position
- C3 (): allylic position ( to double bond in some notations, or the allylic carbon)
- C4 (): homoallylic
Step 2: Apply allylic free radical stability
In free radical bromination (light), the allylic position is most reactive due to:
- Allylic radical stabilization by resonance:
- Bond dissociation energy of allylic C–H is lower (~356 kJ/mol) vs. secondary (~397 kJ/mol)
For but-1-ene: the C3 hydrogen is allylic and most easily replaced.
Answer: Option (b) — -hydrogen
Key Points to Remember:
- Allylic position = most reactive in free radical halogenation
- Allylic radical is stabilized by resonance with the system
- Reactivity: allylic > tertiary > secondary > primary > vinylic
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