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JEE Advanced levelNumerical answerDifficulty 3 of 3st269

The compound shown is 1,2,3,4-tetramethylcyclohexane drawn without stereochemistry. Treat the ring as planar and count configurational isomers only (enantiomers counted separately). How many stereoisomers does it have? Give an integer.

Numerical answer type.

Answer: 10

The four methyl-bearing carbons are all stereocentres, giving up/down patterns. The molecule is symmetric about the C2-C3 bond midpoint, so turning the ring through about that axis maps the pattern onto ; the 4 patterns with and are fixed and the other 12 pair up, giving distinct compounds. Of these, the patterns with and have a mirror plane and give 2 meso compounds; the other 8 are chiral and form 4 pairs of enantiomers. Total: 10.
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