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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st049

Assume that rotation about the inter-ring bond of a biphenyl is blocked when all four ortho positions carry substituents and free otherwise. Which of the following biphenyls are chiral?

  1. A6,6'-Dinitro-1,1'-biphenyl-2,2'-dicarboxylic acid (diphenic acid derivative)
  2. B2,2'-Diiodo-6,6'-dimethyl-1,1'-biphenyl
  3. C2,2',6-Tribromo-1,1'-biphenyl
  4. D2,2',6,6'-Tetramethyl-1,1'-biphenyl

Answer: A, B

Axial chirality requires blocked rotation (four ortho substituents here) and two different ortho groups on each ring. A: each ring has and ortho: chiral. B: each ring has two identical ortho groups: a mirror plane persists, achiral. C: only three ortho substituents, so rotation is free by the stated rule (and one ring would have identical ortho groups): achiral. D: each ring has and ortho and all four ortho positions are occupied: chiral. Correct: A and D.
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