X-Nico

unusual facts about racemic mixture



2-Norbornyl cation

In 1949, Saul Winstein observed that 2-exo-norbornyl brosylate (p-bromobenzenesulfonate) and 2-endo-norbornyl tosylate (p-toluenesulfonate) gave a racemic mixture of the same product, 2-exo-norbornyl acetate, upon acetolysis (see Figure 6).


see also

NMR spectroscopy of stereoisomers

Mosher's acid contains a -CF3 group, so if the adduct has no other fluorine atoms, the 19F NMR of a racemic mixture shows just two peaks, one for each stereoisomer.