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JEE Main levelSingle correct optionDifficulty 2 of 3st234

The compound shown is one stereoisomer of 1,2-dibromocyclohexane. Consider configuration only (treat the ring as planar). Which statement is correct?

  1. AThe compound shown is a meso compound
  2. BThe compound shown is chiral, and its cis diastereomer is a meso compound
  3. CBoth the compound shown and its cis diastereomer are chiral
  4. DThe compound shown is the enantiomer of cis-1,2-dibromocyclohexane

Answer: B

In the drawing the two bromines are on opposite faces of the ring, so this is trans-1,2-dibromocyclohexane. Its stereocentres are (or ) and it has no mirror plane, so it is chiral and exists as a pair of enantiomers. The cis isomer has both bromines on one face; the plane perpendicular to the ring through the midpoint of the C1-C2 bond is a mirror plane, so cis is meso. cis and trans are diastereomers, not enantiomers. Total stereoisomers: 3.
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