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JEE Advanced levelNumerical answerDifficulty 3 of 3st270

The compound shown is 2,4-dibromo-3-chloropentane drawn without stereochemistry. How many of its stereoisomers are meso (optically inactive) compounds? Give an integer.

Numerical answer type.

Answer: 2

C2 and C4 are stereocentres with identical substituent sets. When they have opposite descriptors, , the molecule has a mirror plane through C3, and C3 then becomes pseudoasymmetric: its can point to either side relative to the two enantiomeric arms, giving two distinct meso compounds. When C2 and C4 are both or both , C3 carries two identical groups and is not a stereocentre; this gives one pair of enantiomers. So there are 4 stereoisomers in total, 2 of them meso.
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