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Haloalkanes and Haloarenes question

2020 · 7 Jan · Shift 1 · Q16
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Haloalkanes and Haloarenes question

2020 · 7 Jan · Shift 1 · Q16

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
1- methyl ethylene oxide when treated with an excess of HBr produces :
  1. A
    JEE Main 2020 (Online) 7th January Morning Slot Chemistry - Haloalkanes and Haloarenes Question 124 English Option 1
  2. B
    JEE Main 2020 (Online) 7th January Morning Slot Chemistry - Haloalkanes and Haloarenes Question 124 English Option 2
  3. C
    JEE Main 2020 (Online) 7th January Morning Slot Chemistry - Haloalkanes and Haloarenes Question 124 English Option 3
  4. D
    JEE Main 2020 (Online) 7th January Morning Slot Chemistry - Haloalkanes and Haloarenes Question 124 English Option 4
View written solutionFree

Correct answer: A

  1. Identify the compound

    1-methyl ethylene oxide is the epoxide propylene oxide (also called 1,2-epoxypropane): \ceCH3−CH−CH2\ce{CH3-CH-CH2}\ceCH3−CH−CH2 with an oxygen bridging the last two carbons.

  2. Reaction of epoxide with HBr

    Epoxides react with hydrogen halides by:

    • protonation of the oxygen,
    • followed by ring opening by bromide ion.

    First, one mole of HBr opens the epoxide ring to give a bromo alcohol.

    For propylene oxide, the product is: \ceCH3−CH(OH)−CH2Br\ce{CH3-CH(OH)-CH2Br}\ceCH3−CH(OH)−CH2Br or equivalently under acidic conditions, ring opening gives the bromohydrin.

  3. Effect of excess HBr

    Since HBr is in excess, the alcohol group is further replaced by bromine.

    Thus: \ceCH3−CH(OH)−CH2Br+HBr−>CH3−CHBr−CH2Br+H2O\ce{CH3-CH(OH)-CH2Br + HBr -> CH3-CHBr-CH2Br + H2O}\ceCH3−CH(OH)−CH2Br+HBr−>CH3−CHBr−CH2Br+H2O

  4. Final product

    Therefore, the final product is: \ceCH3−CHBr−CH2Br\ce{CH3-CHBr-CH2Br}\ceCH3−CHBr−CH2Br

    This is 1,2-dibromopropane.

  5. Conclusion

    So, 1-methyl ethylene oxide with excess HBr gives 1,2-dibromopropane.

  6. Comparison with stored answer

    The stored correct answer is A. Since the option texts are not visible, I infer that A corresponds to 1,2-dibromopropane.

    Hence, I agree with the stored answer provided option A is 1,2-dibromopropane.

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