JEE Main · 2019 · Shift-IeasyHC-061

Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of light?

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of light? image

Options
  1. a

    α\alpha-hydrogen

  2. b

    γ\gamma-hydrogen

  3. c

    δ\delta-hydrogen

  4. d

    β\beta-hydrogen

Correct Answerb

γ\gamma-hydrogen

Detailed Solution

Step 1: Identify compound E and its hydrogens

Compound E: \ceCH2=CHCH2CH3\ce{CH2=CH-CH2-CH3} (but-1-ene)

Labeling positions relative to the double bond:

  • C1 (\ceCH2=\ce{CH2=}): vinyl position
  • C2 (\ce=CH\ce{=CH-}): vinyl position
  • C3 (\ceCH2\ce{-CH2-}): allylic position (α\alpha to double bond in some notations, or the allylic carbon)
  • C4 (\ceCH3\ce{-CH3}): 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: \ceCH2=CHCH<>CH2CH=CH\ce{CH2=CH-CH* <-> *CH2-CH=CH}
  • 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) — γ\gamma-hydrogen

Key Points to Remember:

  • Allylic position = most reactive in free radical halogenation
  • Allylic radical is stabilized by resonance with the π\pi system
  • Reactivity: allylic > tertiary > secondary > primary > vinylic

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