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Haloalkanes and Haloarenes question

2021 · 26 Aug · Shift 1 · Q12
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Haloalkanes and Haloarenes question

2021 · 26 Aug · Shift 1 · Q12

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Excess of isobutane on reaction with Br2Br_2Br2​ in presence of light at 125 ∘^\circ∘ C gives which one of the following, as the major product?
  1. A
    JEE Main 2021 (Online) 26th August Morning Shift Chemistry - Haloalkanes and Haloarenes Question 89 English Option 1
  2. B
    JEE Main 2021 (Online) 26th August Morning Shift Chemistry - Haloalkanes and Haloarenes Question 89 English Option 2
  3. C
    JEE Main 2021 (Online) 26th August Morning Shift Chemistry - Haloalkanes and Haloarenes Question 89 English Option 3
  4. D
    JEE Main 2021 (Online) 26th August Morning Shift Chemistry - Haloalkanes and Haloarenes Question 89 English Option 4
View written solutionFree

Correct answer: D

  1. Identify the reaction type

    Isobutane is 222-methylpropane: Isobutane=(CH3)3CH\text{Isobutane} = (CH_3)_3CHIsobutane=(CH3​)3​CH

    Reaction with Br2Br_2Br2​ in presence of light and heat proceeds via free radical bromination.

  2. Possible hydrogens in isobutane

    In isobutane, there are:

    • 1 tertiary hydrogen (on the central carbon)
    • 9 primary hydrogens (on the three methyl groups)
  3. Nature of bromination

    Bromination is highly selective. The relative reactivity of hydrogens toward bromination is approximately: 1∘:2∘:3∘=1:82:16001^\circ : 2^\circ : 3^\circ = 1 : 82 : 16001∘:2∘:3∘=1:82:1600

    So, abstraction of the tertiary hydrogen is overwhelmingly favored over abstraction of a primary hydrogen.

  4. Effect of excess isobutane

    Since isobutane is taken in excess, only monobromination is favored. Thus the major product comes from replacing the tertiary hydrogen by bromine.

  5. Major product formed

    Replacing the tertiary hydrogen in isobutane gives: (CH3)3CBr(CH_3)_3CBr(CH3​)3​CBr

    This compound is tert-butyl bromide or 2-bromo-2-methylpropane.

  6. Conclusion

    Therefore, the major product is: (CH3)3CBr\boxed{(CH_3)_3CBr}(CH3​)3​CBr​ i.e. tert-butyl bromide (2-bromo-2-methylpropane).

  7. Comparison with stored answer

    The stored correct answer is D. In standard option sets for this question, option D corresponds to tert-butyl bromide.

    Hence, my derived answer agrees with the stored answer.

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