Q2(c). Lewis-acid dehydration and rearrangement
Complete the reaction of cyclohexyldimethylcarbinol with boron trifluoride etherate, giving a mechanism and plausible reasons for the product spread. [reaction scheme given in the paper]
Answer in brief
A carbocation network gives mainly substituted alkenes: isopropylidenecyclohexane, isopropenylcyclohexane and 1-isopropylcyclohexene; ring-expanded alkenes are also mechanistically accessible.
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CoversBF₃ etherate dehydrationcarbocation rearrangementhydride shiftring expansionWagner–Meerwein rearrangement
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