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JEE Main levelSingle correct optionDifficulty 2 of 3g2146

Which of the following best explains why ortho-substituted anilines are generally weaker bases than aniline in aqueous solution?

  1. AThe ortho group always increases the electron density on nitrogen
  2. BThe ortho group sterically hinders protonation and solvation of the group, destabilising the anilinium ion
  3. CThe ortho group makes the lone pair more available through the effect of nitrogen
  4. DThe ortho group converts the amine to an amide

Answer: B

On protonation the group needs solvation by water and a less crowded environment. A neighbouring ortho group interferes with both, so the cation is less stabilised and the base is weaker. This is independent of the electronic nature of the group.
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