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JEE Main levelSingle correct optionDifficulty 2 of 3ap267

The ether shown is to be made by a Williamson-type reaction in good yield. Which statement is correct?

  1. ASodium phenoxide with tert-butyl bromide gives it in good yield.
  2. BSodium tert-butoxide with bromobenzene gives it in good yield.
  3. CNeither route works well: the tertiary halide undergoes elimination and the aryl halide does not undergo SN2.
  4. DBoth routes work equally well.

Answer: C

The ether is tert-butyl phenyl ether. Phenoxide with the tertiary halide gives mainly 2-methylpropene by E2 elimination. The aryl carbon of bromobenzene cannot be attacked by , so tert-butoxide does not displace bromide. Neither Williamson route is satisfactory.
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