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JEE Advanced levelNumerical answerDifficulty 3 of 3st314

The compound shown is 1,2-dichloro-3-methylcyclopropane with no configuration specified. Treating the ring as planar and counting configurational stereoisomers only, how many stereoisomers does it have? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 4

Consider the two Cl atoms first. If they are cis, a mirror plane through C3 is possible: the on C3 can be cis or trans to the chlorines, giving two different meso (achiral) compounds; C3 is pseudoasymmetric in these. If the Cl atoms are trans, the molecule is chiral and gives one pair of enantiomers; moving the to the other face then produces the same pair, because C3 is no longer stereogenic. Total = 2 + 2 = 4, less than .
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More questions on Cyclic stereoisomers (cyclopropane, cyclobutane, cyclohexane) from structures