Chapter 14, Problem 14.28P

Draw all constitutional isomers of molecular formula ${\text{C}}_{\text{3}}{\text{H}}_{\text{6}}{\text{Cl}}_{\text{2}}$.

a. How many signals does each isomer exhibit in its ${}^{\text{1}}\text{H}$ NMR spectrum?

b. How many lines does each isomer exhibit in its ${}^{\text{13}}\text{C}$ NMR spectrum?

c. When only the number of signals in both ${}^{\text{1}}\text{H}$ and ${}^{\text{13}}\text{C}$ NMR spectroscopy is considered, is it possible to distinguish all of these constitutional isomers?