Q8(a). Selective epoxidation and carbonyl rearrangement
Identify A and B when the printed methyl cis-bicyclo[3.3.0]octadiene is treated with mCPBA in chloroform and then boron trifluoride etherate. Explain the mechanisms. [structure of the bicyclooctadiene given in the paper]
Model answer
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Topic notes: molecular rearrangements, with every Civil Services, IFoS and Geo-Scientist PYQ →
CoversmCPBA epoxidationMeinwald rearrangementBF₃ etheratebicyclo[3.3.0]octadieneepoxide to carbonyl
All parts of Question 8
- 8(a) Selective epoxidation and carbonyl rearrangement10 marks
- 8(b) A C9H12 alkylbenzene mass spectrum5 marks
- 8(c) Benzene radical anion5 marks
- 8(d) Average repeat-unit mass of a terpolymer5 marks
- 8(e) Identification of glutaric anhydride15 marks