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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc232

The compound shown is a parent aromatic amine. Substituents are placed on the ring in the four structures shown. Which structure is the strongest base in water?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: D

Para-methoxy donates electrons by +R which dominates its -I effect, raising the basicity above aniline (pKa about 5.3). Meta-methoxy shows only -I (about 4.2), and the nitroanilines are much weaker (meta about 2.5, para about 1.0). The para-methoxy compound is the strongest.
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