Q6(b). Ozonolysis of camphene, then Wolff–Kishner reduction
Complete the following reaction and sketch a suitable mechanism for conversion of B → C: A, with O₃ then Zn/CH₃COOH, gives B; B with NH₂NH₂, KOH, Δ gives C. [Structure of A (camphene) given in the paper]
Answer in brief
B = camphenilone (3,3-dimethylbicyclo[2.2.1]heptan-2-one), with HCHO. C = 2,2-dimethylbicyclo[2.2.1]heptane, by Wolff–Kishner reduction.
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CoversozonolysisWolff–Kishner reductioncamphenecamphenilonehydrazone
All parts of Question 6
- 6(a) Chlorocarbene from CH₂Cl₂; ring expansion of 3-methylindole4 marks
- 6(b) Ozonolysis of camphene, then Wolff–Kishner reduction4 marks
- 6(c) Reductive amination, then intramolecular aza-Michael addition4 marks
- 6(d) Benzaldehyde and ethane-1,2-dithiol: a 1,3-dithiolane4 marks
- 6(e) Amidomercuration–demercuration of hex-1-ene in acetonitrile4 marks
- 6(f) Dimerisation of cyclopentadiene: endo rule by frontier orbitals4 marks
- 6(g) Two isomeric esters C₇H₁₄O₂ from ¹H NMR4 marks
- 6(h) Mass spectrum of 3-butyn-2-ol: the ion of m/z 554 marks
- 6(i) Acetone: solvent shift of the n → π* band4 marks
- 6(j) Butyrophenone: McLafferty rearrangement and α-cleavage4 marks