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JEE Advanced levelNumerical answerDifficulty 3 of 3st322

The compound shown is one dimethylcyclohexane. Consider all constitutional isomers of dimethylcyclohexane (1,1-, 1,2-, 1,3- and 1,4-) and count every configurational stereoisomer of each, treating the ring as planar and counting enantiomers separately. What is the total number of dimethylcyclohexane stereoisomers? Give the answer as an integer.

Numerical answer type, tolerance 0.5.

Answer: 9

1,1-Dimethylcyclohexane has no stereoisomers: 1. 1,2-Dimethylcyclohexane: cis is meso, trans is a pair of enantiomers: 3. 1,3-Dimethylcyclohexane: cis is meso, trans is a pair of enantiomers: 3. 1,4-Dimethylcyclohexane: cis and trans, both achiral, no stereocentres: 2. Total = 1 + 3 + 3 + 2 = 9.
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