Q6(a). Singlet and triplet carbenes; fluorenylidene with cis-but-2-ene
Carbenes exist in singlet and triplet states. Which of the two states of carbenes is non-stereospecific in its reaction with alkenes? Explain why. Predict the product/s formed in the following reaction: [9-diazofluorene, hν, cis-2-butene → ?; scheme given in the paper]
Answer in brief
The triplet carbene is non-stereospecific. Product: a mixture of cis- and trans-2,3-dimethylspiro[cyclopropane-1,9′-fluorene].
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Coverssinglet carbenetriplet carbenefluorenylidenecyclopropanationstereospecific addition9-diazofluorene
All parts of Question 6
- 6(a) Singlet and triplet carbenes; fluorenylidene with cis-but-2-ene4 marks
- 6(b) Bromine addition: styrene reacts faster than propene4 marks
- 6(c) Addition of HCl to an α,β-unsaturated acid4 marks
- 6(d) Michael addition of a cyclic 1,3-dione to cyclohex-2-enone4 marks
- 6(e) Hydroboration–oxidation of 1-methylcyclohexene4 marks
- 6(f) Cope rearrangement of a 1,5-diene4 marks
- 6(g) Diels–Alder reaction: product and reactants4 marks
- 6(h) IR distinction: hydrogen bonding and ring strain4 marks
- 6(i) McLafferty rearrangement: 2-pentanone and 3-pentanone4 marks
- 6(j) NMR assignment of 4-methylpent-1-yne4 marks