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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3st274

The compound shown is 1,2,3,4-tetrachlorocyclobutane drawn without stereochemistry. Treat the ring as planar and square and consider configuration only. Which of the following statements are correct?

  1. AIt has exactly 4 stereoisomers
  2. BAll of its stereoisomers are achiral
  3. CIt has 16 stereoisomers because it has four stereocentres
  4. DAt least one of its stereoisomers is chiral

Answer: A, B

Each ring carbon carries one and one , so the stereoisomers are the distinct up/down patterns of four chlorines on a square: all four up; three up and one down; two adjacent up and two adjacent down; and two opposite up and two opposite down. Any other pattern is one of these rotated or turned over. That is 4 stereoisomers. Each of these patterns has a mirror plane perpendicular to the ring (through two opposite carbons or through two opposite bond midpoints), so all four are achiral and the count is far too high.
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