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A Levels Chemistry (9701)•9701/12/O/N/23
Question 27 from 9701/12/O/N/23

Explanation

Counting chiral centers in artemisinin's structure

Steps:

  • Examine artemisinin's formula: C15H22O5, a sesquiterpene with peroxide bridge and lactone ring.
  • Identify chiral centers as tetrahedral carbons bonded to four different groups.
  • Locate them at C1 (bridgehead), C5 (peroxide attachment), C6 (methyl group), C7 (peroxide), C8 (side chain), C9 (ring junction), and C12 (lactone).
  • Total: seven chiral carbons confirmed by standard stereochemistry analysis.

Why C is correct:

  • A chiral center requires a carbon with four distinct substituents; artemisinin has exactly seven such atoms per IUPAC definition.

Why the others are wrong:

  • A: Ignores three centers in the bicyclic and peroxide regions.
  • B: Misses the C12 lactone carbon.
  • D: Counts the oxygen in the peroxide as chiral, which it is not.

Final answer: C

Topic: An introduction to organic chemistry

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