Q10(d). Frost circles and aromaticity
Use Frost-circle diagrams to explain why cyclooctatetraene is not aromatic but the cyclopropenyl cation is aromatic.
Answer in brief
The three-membered cation has a filled bonding MO with two electrons; planar COT would have a destabilising eight-electron open-shell arrangement and distorts out of plane.
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CoversFrost circlesaromaticityCyclic molecular orbitals
All parts of Question 10
- 10(a) Chlorinated allylic structure10 marks
- 10(b) Acetylacetone proton NMR5 marks
- 10(c) Activated Hofmann elimination5 marks
- 10(d) Frost circles and aromaticity10 marks