In the mass spectrum of compound $X$, $\text{C}_5\text{H}_{10}\text{O}_2$, the peak heights are 22.65 for the M peak and 1.25 for the M+1 peak. Use these readings to demonstrate that one molecule of $X$ contains five carbon atoms. Show your working.
The mass spectrum shows a peak at $m/e = 57$. Finish the equation to show how $X$ fragments to give this peak: $[\text{C}_5\text{H}_{10}\text{O}_2]^+ \rightarrow$ ... + ...
State the function of TMS and $\text{CDCl}_3$ in NMR spectroscopy.
The proton NMR spectrum of compound $X$, $\text{C}_5\text{H}_{10}\text{O}_2$, is shown. By considering both the relative peak areas and their $\delta$ values, use the Data Booklet to deduce: the part of the molecule producing the peak at $\delta = 2.2$; the part of the molecule producing the peaks at $\delta = 1.2$ and $\delta = 3.5$; and the part of the molecule producing the peak at $\delta = 4.0$.
When $X$ is reacted with aqueous alkaline iodine, a yellow precipitate forms. Use this information together with your answers to (c)(i) to propose a structure for $X$.
Compound $W$ is an ester with the molecular formula $\text{C}_5\text{H}_{10}\text{O}_2$. Its proton NMR spectrum shows just two peaks. The ratio of the areas of these peaks is $9 : 1$. Suggest a structure for this ester, $W$.
Compound $V$ is a carboxylic acid containing a chiral centre. Its molecular formula is also $\text{C}_5\text{H}_{10}\text{O}_2$. Explain what is meant by the term chiral centre.
Suggest a structure for $V$.