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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3hx159

Chlorobenzene labelled with at the carbon bearing (C-1) is treated with in liquid . Which statements are correct? (Ignore isotope effects.)

  1. AAll the remains at the carbon bearing because substitution is a direct displacement
  2. BThe reaction goes via a Meisenheimer complex
  3. CThe aniline obtained is a roughly 1 : 1 mixture of the compound with at the carbon bearing and the compound with at the carbon ortho to it
  4. DThe intermediate is benzyne, in which the two adjacent carbons are equivalent in their reactivity to

Answer: C, D

Elimination of gives benzyne with the triple bond between C-1 (labelled) and C-2. The amide ion attacks either carbon with equal probability, giving aniline labelled at the C-NH2 carbon about half the time and at the neighbouring carbon half the time. The unactivated ring has no nitro groups, so the addition-elimination path is not followed.
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