Q10(c). Cope rearrangement of cis-2,3-divinyloxirane
Identify the product Y for the thermal sigmatropic reaction of X (Δ). Name the reaction and give suitable mechanism. [Structure of X given in the paper]
Answer in brief
Cope rearrangement ([3,3]-sigmatropic shift). Y = 4,5-dihydrooxepine, C₆H₈O.
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CoversCope rearrangement[3,3]-sigmatropic shiftdivinyloxiranedihydrooxepineboat transition state
All parts of Question 10
- 10(a) Perkin reaction, then three steps to 2-methylindane10 marks
- 10(b) 4π ring opening, then 6π ring closure: the intermediate II5 marks
- 10(c) Cope rearrangement of cis-2,3-divinyloxirane5 marks
- 10(d) Structure from mass, IR and NMR spectra: a bromo acid10 marks