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JEE Main · 2017 · 02 Apr 2017 · Offline · Haloalkanes and Haloarenes

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Which of the following, upon treatment with tert-BuONa followed by addition of bromine water, fails to decolourize the colour of bromine?
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
    ✓ Correct
  4. (D)(see structure)

Answer: (C)

Solution

Treatment with the strong base tert-BuONa sets up an E2 elimination to an alkene, and an alkene immediately decolourises bromine water. The structure that cannot make such an alkene — the one with no suitable -hydrogen to eliminate — produces no alkene and so leaves the bromine colour standing.

JEE Main · 2017 · 02 Apr 2017 · Offline · Single correct option

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