Chapter 14, Problem 9PP

Practice Problem 14.9

In 1967 R. Breslow (of Columbia University) and co-workers showed that adding $SbC{l}_5$ to a solution of 3-chlorocyclopropene in $C{H}_{2}C{l}_2$ caused the precipitation of a white solid with the composition $C_3{H}_3{}^{+}SbC{l}_6{}^{-}$. NMR spectroscopy of a solution of this salt showed that all of its hydrogen atoms were equivalent.

(a) What new aromatic ion had these researchers prepared?

(b) How many ${}^{13}C$ NMR signals would you predict for this ion?