JEE Main · 2019 · Shift-IIeasyHC-128

What will be the major product in the following mononitration reaction?

Hydrocarbons · Class 11 · JEE Main Previous Year Question

Question

What will be the major product in the following mononitration reaction? image

Options
  1. a

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  2. b

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  3. c

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  4. d

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Correct Answerd

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Detailed Solution

image Nitration occurs preferentially on the more electron-rich ring:

  • Ring A (activated by \ceNH\ce{-NH-}): more reactive
  • Ring A is ortho/para directed by \ceNH\ce{-NH-}
  • Para position of Ring A (para to N) = major product

Product = \ce4NO2C6H4NHCOC6H5\ce{4-NO2-C6H4-NH-CO-C6H5} (4-nitrobenzanilide)

Key Points:

  • Benzanilide: ring with \ceNH\ce{-NH-} group is activated; ring with \ceCO\ce{-CO-} is deactivated
  • Nitration occurs on the more reactive (amino) ring
  • \ceNHCO\ce{-NHCO-} directs ortho/para; para preferred (less steric)
  • Product: para-nitro on the N-phenyl (aniline) ring

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