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JEE Advanced levelNumerical answerDifficulty 3 of 3st229

The compound shown is 2,3,4,5-tetrachlorohexane drawn without stereochemistry. Counting only configurational isomers, how many of its stereoisomers are achiral (meso forms)? Give an integer.

Numerical answer type.

Answer: 2

The molecule has four stereocentres and is constitutionally symmetric about the C3-C4 bond. Of the configurations, those in which C2/C5 and C3/C4 have opposite descriptors (R,R,S,S read from one end and S,S,R,R from the other) have a mirror plane, and these give 2 distinct meso compounds: and . The remaining 8 chiral isomers form 4 enantiomeric pairs, so the total is 10 stereoisomers, 2 of them meso.
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