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Haloalkanes and Haloarenes question

2019 · 10 Jan · Shift 1 · Q11
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Haloalkanes and Haloarenes question

2019 · 10 Jan · Shift 1 · Q11

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of light ? JEE Main 2019 (Online) 10th January Morning Slot Chemistry - Haloalkanes and Haloarenes Question 137 English
  1. A
    β−\beta -β− hydrogen
  2. B
    α−\alpha -α− hydrogen
  3. C
    γ−\gamma -γ− hydrogen
  4. D
    δ−\delta -δ− hydrogen
View written solutionFree

Correct answer: C

  1. Key idea: free-radical bromination in presence of light
    Bromination with Br2/hν\mathrm{Br_2/h\nu}Br2​/hν proceeds by a free-radical substitution mechanism. In such reactions, the hydrogen that is removed most easily is the one whose abstraction forms the most stable radical.

  2. Rule for selectivity of bromination
    Bromine is highly selective. So, the preferred hydrogen is the one that gives a radical stabilized by:

    • resonance,
    • benzylic stabilization,
    • allylic stabilization,
    • or greater alkyl substitution.
  3. Application to compound (E)
    In compound (E)(E)(E), the hydrogen labeled as γ\gammaγ-hydrogen is the one whose removal leads to the most stabilized radical intermediate during bromination. Hence, that hydrogen is replaced most easily.

  4. Evaluation of options

    1. A: β\betaβ-hydrogen — not the most favorable.
    2. B: α\alphaα-hydrogen — not the most favorable.
    3. C: γ\gammaγ-hydrogen — most easily replaceable.
    4. D: δ\deltaδ-hydrogen — not the most favorable.
  5. Final answer
    Therefore, the hydrogen easily replaceable during bromination in presence of light is: γ-hydrogen\boxed{\gamma\text{-hydrogen}}γ-hydrogen​ So the correct option is C.

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