question_answer 72)

  Predict the product of reaction of aniline with bromine in non-polar solvent such as .

Answer:

                  In non-polar solvents, the resonance structures involving separation of +Ve and -ve charges (refer to structure II-IV, page 13/20) are not stabilized by dipole-dipole interactions with the non-polar solvent. As a result, activating effect of the  is reduced and hence monosubstitution occurs only at o- and 4-positions giving a mixture of 2-bromoaniline (minor) and 4-bromoaniline (major). For structures refer to page 13/34.