Past exam of the chemistry course of the year 3 of the natural sciences course of the University of Cambridge / 2022 / Paper 4 / 55 / c / iii / Solution

No stereochemical information need survive from the starting carbinol. Ionization converts that tetrahedral stereocentre into a planar, delocalized propargyl/allenyl cation before cyclization. In achiral conditions the two enantiomeric pathways to the new stereocentre in the tert-butyl-derived product are equivalent, so an enantiopure alcohol is expected to give racemic product. A claim of retained enantiopurity would require evidence for unusually effective conformational memory or ion-pair control.