Q4(e). Pinacol and Tiffeneau–Demjanov rearrangements
Predict the products of (i) the fluorenyl/diphenyl vicinal diol in acid and (ii) 1-(aminomethyl)cyclopentan-1-ol with nitrous acid at 0 °C. [structure of the diol given in the paper]
Model answer
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Topic notes: molecular rearrangements, with every Civil Services, IFoS and Geo-Scientist PYQ →
Coverspinacol–pinacolone rearrangementTiffeneau–Demjanov rearrangementring expansionnitrous acidcyclohexanone
All parts of Question 4
- 4(a) Two electrophilic additions with unusual outcomes5 marks
- 4(b) Rates of alkoxide-induced elimination5 marks
- 4(c) Regioselective Diels–Alder addition5 marks
- 4(d) Knoevenagel condensation5 marks
- 4(e) Pinacol and Tiffeneau–Demjanov rearrangements5 marks
- 4(f) Buchner ring expansion5 marks
- 4(g) Two substrates, one Favorskii intermediate10 marks