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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3206

Which statements about the reaction of chlorobenzene with in liquid and about benzyne are correct?

  1. AThe aromatic sextet of benzyne is not disrupted by the extra bond
  2. BIf C-1 of chlorobenzene is labelled, the aniline is formed with equal amounts of on the labelled carbon and on the neighbouring carbon
  3. C4-Chlorotoluene gives 4-methylaniline as the only amine product
  4. DThe extra bond of benzyne is formed by in-plane overlap of two orbitals and lies orthogonal to the aromatic system

Answer: A, B, D

The in-plane extra bond of benzyne is perpendicular to the cloud, so the sextet is retained, but the bond is weak because the orbitals overlap poorly. The label scrambles 1:1 because the amide adds to either end of the symmetrical aryne. 4-Chlorotoluene gives 3- and 4-methylaniline in similar amounts, so the last statement is false.
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