(Solved): 5. A compound of molecular formula C8H14O produces the 1H NMR spectrum shown in Figure 22.47. ...

5. A compound of molecular formula ${\mathrm{C}}_8{\mathrm{H}}_{14}\mathrm{O}$ produces the ${}^1\mathrm{H}$ NMR spectrum shown in Figure 22.47. Its infrared spectrum shows a strong carbonyl stretching peak, which indicates that ${\mathrm{C}}_8{\mathrm{H}}_{14}\mathrm{O}$ is either an aldehyde or a ketone. Deduce the structure of the compound, estimate the chemical shifts of the different types of protons, using the parameters in Tables 22.3-22.5, and assign all the NMR signals. .