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Haloalkanes and Haloarenes question

2017 · Shift 0 · Q6
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Haloalkanes and Haloarenes question

2017 · Shift 0 · Q6

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to decolorize the colour of bromine?
  1. A
    JEE Main 2017 (Offline) Chemistry - Haloalkanes and Haloarenes Question 154 English Option 1
  2. B
    JEE Main 2017 (Offline) Chemistry - Haloalkanes and Haloarenes Question 154 English Option 2
  3. C
    JEE Main 2017 (Offline) Chemistry - Haloalkanes and Haloarenes Question 154 English Option 3
  4. D
    JEE Main 2017 (Offline) Chemistry - Haloalkanes and Haloarenes Question 154 English Option 4
View written solutionFree

Correct answer: A

  1. Key idea of the reaction sequence

    The reagent tert-BuONa\text{tert-BuONa}tert-BuONa is a strong, bulky base, so with haloalkanes it generally gives elimination to form an alkene.

    Then, on adding bromine water, compounds containing a carbon-carbon double bond usually decolorize bromine due to addition across the double bond.

    Therefore, the compound that fails to decolorize bromine water must be the one that does not form an alkene on treatment with tert-BuONa\text{tert-BuONa}tert-BuONa.

  2. What kind of substrate will not give elimination?

    Elimination requires a β\betaβ-hydrogen. If the substrate has no β\betaβ-hydrogen, then E2E2E2 elimination cannot occur.

    A classic example is neopentyl halide type structure, where the carbon adjacent to the carbon bearing halogen has no hydrogen available for elimination.

  3. Interpretation of the question

    Since the options are not visible in the prompt, the only way to identify the intended answer is by the stored correct answer and the underlying concept.

    The option that fails to decolorize bromine water must be the substrate that cannot undergo dehydrohalogenation with tert-BuONa\text{tert-BuONa}tert-BuONa, i.e. the one lacking a suitable β\betaβ-hydrogen.

  4. Comparison with stored answer

    The stored correct answer is A. This is consistent if option A is the substrate with no β\betaβ-hydrogen and hence no alkene formation.

  5. Final conclusion

    Hence, the compound in option A fails to decolorize bromine water.

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