Q6(f). trans- and cis-Cyclohexane-1,2-diol from cyclohexanone
How will you synthesize the compounds X (trans-cyclohexane-1,2-diol) and Y (cis-cyclohexane-1,2-diol) from cyclohexanone by using suitable reagents? [structures given in the paper]
Answer in brief
First make cyclohexene (NaBH₄; then acid, heat). X (trans): peroxy acid, then H₃O⁺ (anti addition). Y (cis): OsO₄/NMO or cold dilute alkaline KMnO₄ (syn addition).
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The full model answer
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CoversdihydroxylationOsO4epoxidationanti additionsyn additioncyclohexane-1,2-diol
All parts of Question 6
- 6(a) Curtius rearrangement; the isocyanate closes to a cyclic urea4 marks
- 6(b) HBr and a conjugated diene: 1,2- and 1,4-addition4 marks
- 6(c) Phenylglycine and mandelic acid from benzaldehyde4 marks
- 6(d) Coumarin and 3-acetylcoumarin from salicylaldehyde4 marks
- 6(e) Intramolecular oxymercuration–demercuration: a cyclic ether4 marks
- 6(f) trans- and cis-Cyclohexane-1,2-diol from cyclohexanone4 marks
- 6(g) [1,5]-Carbon shift and Cope rearrangement4 marks
- 6(h) Four C₁₀H₁₄ isomers: the one marked by a McLafferty peak4 marks
- 6(i) C₃H₇NO with two N–methyl singlets: N,N-dimethylformamide4 marks
- 6(j) ν(C=C) of methylidenecycloalkanes and ring size4 marks