A sample of ethyl propanoate, \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2}
\mathrm{CH}_{2} \mathrm{CH}_{3}\), is
investigated by \(^{1} \mathrm{H} \mathrm{NMR}\) and \(^{13} \mathrm{C}\) NMR
(proton decoupled) spectroscopy and mass spectrometry. (Sections \(12.1-12.3\) )
(a) Draw the expected \(^{1} \mathrm{H}\) NMR spectrum showing spin-spin
splittings and approximate chemical shifts.
(b) Draw the expected \(^{13} \mathrm{C}\) NMR spectrum (proton decoupled) with
approximate chemical shifts.
(c) In the mass spectrum, an intense peak was observed at \(m / z\) 57. Draw the
structure of the cation that corresponds to this peak and give a mechanism for
its formation.
