Q2(b). Halohydrin cyclization and chair populations
Rank the three drawn methylcyclohexane chlorohydrins I–III in decreasing tendency to form an epoxide. [structures of chlorohydrins I–III given in the paper]
Answer in brief
The expected order is II > I ≫ III.
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Coversepoxide formationhalohydrintrans-diaxial arrangementintramolecular SN2neighbouring group participationconformational analysis
All parts of Question 2
- 2(a) Third- and fourth-order Cannizzaro kinetics10 marks
- 2(b) Halohydrin cyclization and chair populations10 marks
- 2(c) Lewis-acid dehydration and rearrangement10 marks
- 2(d) Butanone phenylhydrazone and Fischer cyclization10 marks