Chapter 38

You are trying to identify a compound \(M_{\mathrm{r}}=126\). Infrared, \({ }^{1} \mathrm{H}-\) and \({ }^{13} \mathrm{C}\)-NMR spectroscopy have indicated thatit is either \(\mathrm{CH}_{3} \mathrm{CH}_{2}-\mathrm{COOCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}\) or \(\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{COOCH}_{2} \mathrm{CH}_{3}\), but have not provided enough detail for a satisfactory conclusion. Predict the mass spectra of the two compounds from the possible \(\alpha\) - and \(\beta\)-cleavages for each molecule so that a distinction can be made.