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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc234

Select all the correct statements about the compound shown.

  1. AThe free amino group is the more basic nitrogen
  2. BThe nitrogen of the acetamido group is essentially non-basic because its lone pair is delocalised onto the carbonyl
  3. CThe free amino group is a stronger base than the amino group of 4-nitroaniline
  4. DThe free amino group is more basic than that of cyclohexylamine

Answer: A, B, C

The compound shown is 4-aminoacetanilide. The acetamido nitrogen lone pair is tied up by amide resonance, so the NH2 on the ring is the basic site. Acetamido is only weakly electron withdrawing/donating relative to the strongly withdrawing nitro group, so this NH2 is more basic than in 4-nitroaniline. Any aromatic amine is far less basic than cyclohexylamine, so the last statement is false.
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