Treatment of Tert-Butyl Alcohol with Hydrogen Chloride Yields a Mixture

Essay

Treatment of tert-butyl alcohol with hydrogen chloride yields a mixture of tert-butyl chloride and 2-methylpropene. $$\left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { COH } \stackrel { \mathrm { HCl } } { \longrightarrow } \left( \mathrm { CH } _ { 3 } \right) _ { 3 } \mathrm { CCl } + \left( \mathrm { CH } _ { 3 } \right) _ { 2 } \mathrm { C } = \mathrm { CH } _ { 2 }$$ a) After chromatographic separation, how would you use $^1H$ NMR to help you decide which was which?

b) How would the ${}^{13}C$ NMR for the two compounds differ?