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A Levels Chemistry (9701)•9701/11/M/J/23
Question 24 from 9701/11/M/J/23

Explanation

Total structural and stereoisomers for five-membered ring tertiary alcohols Steps:

  • Identify structural isomers featuring a five-membered ring and tertiary OH group, considering possible carbon skeletons like substituted cyclopentanes.
  • Classify each: 3 achiral structures (no chiral centers, 1 isomer each), 1 structure with one chiral center (2 stereoisomers), 1 structure with two non-identical chiral centers (4 stereoisomers).
  • Calculate total: 3 (achiral) + 2 (one chiral) + 4 (two chirals) = 9 isomers.
  • Verify no meso forms or identical chirals, as centers are non-identical per the given condition.

Why C is correct:

  • 9 matches the sum of structural variants and their stereoisomers, with 2²=4 for the di-chiral case as stated.

Why the others are wrong:

  • A: Counts only the 4 stereoisomers from the di-chiral structure, ignoring structural isomers.
  • B: Counts only the 5 structural isomers, omitting stereoisomers.
  • D: Overcounts by assuming identical chiral centers or additional invalid structures, exceeding the valid total.

Final answer: C

Topic: Hydroxy compounds

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