Compound F has $31.4\%$ oxygen by mass, and its mass spectrum shows a molecular ion peak at $m/e = 102$. Use every piece of this information to show that the molecular formula of compound F is $\text{C}_5\text{H}_{10}\text{O}_2$. Show all your working.
The first isomer has already been drawn. Draw the skeletal formulae of the three remaining structural isomers.
State the systematic name of isomer 1.
F is one of the four structural isomers in (b)(i). A carbon-13 NMR spectrum of F is shown. Use the spectrum to identify isomer F. Draw its structure in the box below.
Use the Data Booklet together with your knowledge of carbon-13 NMR spectroscopy to identify the environments and hybridisations of the carbon atoms responsible for the three absorptions at $\delta = 27\,\text{ppm}$, $41\,\text{ppm}$ and $179\,\text{ppm}$.
G is another one of the four structural isomers in (b)(i). The proton NMR spectrum of G is shown. Use the Data Booklet and the spectrum to complete the table below. The actual chemical shifts for the four absorptions in G and the splitting pattern at $\delta = 1.6\,\text{ppm}$ have been supplied for you.
Deduce which isomer is G and draw its structure in the box.
Name or give the formula of a suitable solvent for obtaining a proton NMR spectrum.