The mass spectrum indicates an $m/e$ value of 90 for the M peak. The peak heights for M and M+1 are in the ratio $22.1 : 0.7$. Use this ratio to work out how many carbon atoms are present in one molecule of F.
Suggest the molecular formula for compound F.
The infra-red spectrum of F was recorded. Use the Data Booklet and your knowledge of infra-red spectroscopy to identify the bond type and functional group responsible for the three absorptions at $3350\,\text{cm}^{-1}$, $2680\,\text{cm}^{-1}$ and $1725\,\text{cm}^{-1}$.
In the mass spectrum, the M peak has $m/e$ value 90. The peak-height ratio for M to M+1 is $22.1 : 0.7$.
F was dissolved in deuterated trichloromethane, $\text{CDCl}_3$, and the proton NMR spectrum of the resulting solution was obtained.
Use the Data Booklet together with your response to (a)(ii) to fill in Table 1 for the proton NMR spectrum of F. The four chemical-shift values for F have already been provided.
Describe and explain how the absorption at $\delta = 1.4$ is split.
F was dissolved in $\text{D}_2\text{O}$ and the proton NMR spectrum of the new solution was obtained. Two of the absorptions in Table 1 were absent from this spectrum. Which absorptions were absent?
Suggest the structural formula of F.
Cycloheptadiene, $\text{C}_7\text{H}_{10}$, is made up of a seven-membered ring containing two carbon-carbon double bonds.
Complete the skeletal formulae for two isomers of cycloheptadiene.
Predict how many peaks will appear in the carbon-13 NMR spectra of P and Q.