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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx090

Which of the following aryl bromides cannot be converted directly into the corresponding arylmagnesium bromide by treatment with in dry ether?

  1. A4-bromoaniline
  2. B4-bromotoluene
  3. C4-bromoanisole
  4. D4-bromobenzoic acid

Answer: A, D

Any substituent with an acidic or hydrogen protonates the Grignard carbanion as it forms. The carboxylic acid and the primary aromatic amine have such hydrogens. The methyl and methoxy substituents have none, so these bromides give Grignard reagents normally.
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