Q2(c). Rearrangement of a bornane alcohol
Give the product and mechanism for the bicyclic (bornane) alcohol A with acid, naming the rearrangement. [structure of alcohol A given in the paper]
Model answer
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Topic notes: molecular rearrangements, with every Civil Services, IFoS and Geo-Scientist PYQ →
CoversWagner–Meerwein rearrangementborneol to camphenebicyclic carbocation1,2-alkyl shiftterpene rearrangement
All parts of Question 2
- 2(a) Two eliminations from a meso dibromide10 marks
- 2(b) Favorskii rearrangement of a dibromoketone10 marks
- 2(c) Rearrangement of a bornane alcohol10 marks
- 2(d) Claisen rearrangement of an allyl vinyl ether5 marks
- 2(e) Deuterium and hydrolysis rate5 marks