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A Levels Chemistry (9701)•9701/13/M/J/22
Question 33 from 9701/13/M/J/22

Explanation

Iodoform test identifies methyl ketones and oxidizable alcohols in hydroxy carbonyls

Steps:

  • Molecular formula C3H6O2 accommodates structural isomers with one carbonyl (aldehyde or ketone) and one OH group.
  • The isomers are 3-hydroxypropanal (HOCH₂CH₂CHO), 2-hydroxypropanal (CH₃CH(OH)CHO), and 1-hydroxypropan-2-one (CH₃COCH₂OH).
  • 1-Hydroxypropan-2-one contains CH₃CO- group, undergoes triiodination and cleavage to CHI₃ at room temperature.
  • 2-Hydroxypropanal's secondary OH oxidizes to CH₃COCHO (methylglyoxal), a methyl ketone equivalent that gives CHI₃; 3-hydroxypropanal's primary OH oxidizes to OHCCH₂CHO (malonaldehyde), whose active CH₂ enables analogous reaction to CHI₃.

Why B is correct:

  • Exactly three isomers exist, and all react positively per haloform mechanism to form yellow CHI₃ crystals.

Why the others are wrong:

  • A: Misses that all three isomers qualify under iodoform conditions.
  • C: Exceeds the three valid structural isomers.
  • D: Exceeds the three valid structural isomers.

Final answer: B

Topic: Carbonyl compounds

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