A-LevelChemistryOrganic synthesis9701/12 · May/June 2011 · Q291 Mark
This question should be answered by considering the reactions of KMnO4 with different functional groups under the stated conditions. The diagram shows the structure of the naturally-occurring molecule cholesterol. [Figure 29.1] Cholesterol is separately treated with • cold, dilute acidified KMnO4, • hot, concentrated acidified KMnO4. What is the change in the number of chiral carbon atoms in the molecule during each reaction?
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Acold, dilute acidified KMnO4: +1, hot, concentrated acidified KMnO4: 0
Bcold, dilute acidified KMnO4: +1, hot, concentrated acidified KMnO4: -1
Ccold, dilute acidified KMnO4: +2, hot, concentrated acidified KMnO4: 0
Dcold, dilute acidified KMnO4: +2, hot, concentrated acidified KMnO4: -1
✓ Correct answer
D: cold, dilute acidified KMnO4: +2, hot, concentrated acidified KMnO4: -1
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