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JEE Advanced levelSingle correct optionDifficulty 3 of 3st271

The compound shown is 4-methylhepta-2,5-diene drawn without stereochemistry. Counting geometrical and optical isomers together, the total number of stereoisomers is

  1. A8
  2. B6
  3. C4
  4. D3

Answer: C

Both double bonds can be or . When the two double bonds have the same geometry, or , C4 carries two identical propenyl groups and is not a stereocentre, giving 1 achiral compound each: 2. When the geometries differ, , C4 carries two different groups and becomes a stereocentre, giving a pair of enantiomers: 2. The naive count is wrong because of the symmetry. Total: .
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