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JEE Main levelSingle correct optionDifficulty 2 of 3st275

The compound shown is hex-4-ene-2,3-diol drawn without stereochemistry. Counting geometrical and optical isomers together, the total number of stereoisomers is

  1. A4
  2. B6
  3. C8
  4. D16

Answer: C

C2 carries , , and C3; C3 carries , , C2 and the propenyl group. Both are stereocentres. The bond has and C3 on C4 and and on C5, so it is or . The two ends of the molecule are different, so there is no meso form and no coincidence: total stereoisomers.
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