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JEE Advanced levelSingle correct optionDifficulty 3 of 3st287

The compound shown is 1,2-dichloro-3-methylcyclopropane with both chlorine atoms and the methyl group on the same face of the ring. Which statement is correct?

  1. AThe molecule is achiral, and the ring carbon bearing is a pseudoasymmetric centre with descriptor
  2. BThe molecule is chiral because it has three stereocentres
  3. CThe molecule is achiral, and the ring carbon bearing is not stereogenic: moving the to the other face gives the same compound
  4. DThe molecule is chiral and has stereoisomers

Answer: A

With both Cl cis, C1 and C2 have opposite configurations ( and ), and a mirror plane passes through C3 and bisects the C1-C2 bond, so the molecule is achiral. C3 carries H, , (R)- and (S)- arms: constitutionally identical arms of opposite configuration, so C3 is pseudoasymmetric. Moving to the other face gives a different (diastereomeric) meso compound, so C3 is stereogenic. With ranked above , the all-cis arrangement shown has the descriptor at C3; the constitution has 4 stereoisomers in total (two meso forms and one pair of enantiomers).
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