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NEET levelSingle correct optionDifficulty 1 of 3st305

The compound shown is cis-1,2-dibromocyclohexane. Counting cis and trans forms and enantiomers separately (configuration only), the total number of stereoisomers of 1,2-dibromocyclohexane is

  1. A2
  2. B3
  3. C4
  4. D1

Answer: B

1,2-Dibromocyclohexane has two equivalent stereocentres. The cis isomer shown, (1R,2S), has a mirror plane bisecting the C1-C2 bond and is a single meso compound. The trans isomer, with the bromines on opposite faces, has no such plane and exists as a pair of enantiomers, (1R,2R) and (1S,2S). Total = 1 + 2 = 3, fewer than the maximum of because of the meso form.
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More questions on Cyclic stereoisomers (cyclopropane, cyclobutane, cyclohexane) from structures