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JEE Advanced levelSingle correct optionDifficulty 3 of 3st035

3-Isopropylpenta-1,3-diene, , is drawn with the methyl group on C4 and the isopropyl group on C3 on the same side of the C3=C4 bond. Choose the correct descriptor and reason.

  1. A; vinyl outranks isopropyl
  2. B; isopropyl outranks vinyl
  3. C; isopropyl outranks vinyl
  4. D; vinyl outranks isopropyl

Answer: A

On C3 compare vinyl and isopropyl. Both are at the first sphere (vinyl has a duplicate carbon). At the next sphere the vinyl branches are (the carbon, with a duplicate carbon) and (the duplicate), whereas the isopropyl branches are twice. The first-ranked branch decides: , so vinyl wins. The C4 methyl is cis to isopropyl, hence trans to vinyl: .
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