Q10(c). Chemoselective epoxidation
Predict separately the products of the depicted isopropenyl-substituted cyclohexenecarboxylate with (i) RCO₃H and (ii) alkaline H₂O₂. Explain.
Answer in brief
Peracid preferentially epoxidises the isolated isopropenyl group; alkaline peroxide targets the ester-conjugated ring C=C.
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CoversChemoselective epoxidationElectrophilic and nucleophilic oxidants
All parts of Question 10
- 10(a) Identification of a phenolic propenyl aromatic compound10 marks
- 10(b) Bulky substituents and diene conformation5 marks
- 10(c) Chemoselective epoxidation10 marks
- 10(d) Cyclohexanone mass fragmentation5 marks