Past exam of the medicine course of the University of Oxford / 1864 / First examination / Chemistry / 2

What formula would you assign to a substance which gave the following results to analysis :—

and of which the vapour density was 3.05.

The molecular formula is $\boxed{{\mathrm{C}}_4{\mathrm{H}}_8{\mathrm{O}}_2}$, interpreting the vapour density as relative to air. The organic elemental analysis first determines a simpler empirical formula; the vapor-density molar mass measurement then fixes its multiple.

Take 100 mass units of the chemical substance and divide each elemental contribution by its rounded relative atomic mass:The empirical formula is therefore ${\mathrm{C}}_2{\mathrm{H}}_4\mathrm{O}$, with empirical formula mass approximately 44. Its calculated mass percentages are 54.55% carbon, 9.09% hydrogen and 36.36% oxygen. The small discrepancies from the given organic elemental analysis are consistent with rounded experimental data; they should not be converted into large, meaningless integer subscripts.

For equal volumes of ideal gases at equal temperature and pressure, the density ratio equals the molar mass ratio. On the air convention,Doubling ${\mathrm{C}}_2{\mathrm{H}}_4\mathrm{O}$ gives ${\mathrm{C}}_4{\mathrm{H}}_8{\mathrm{O}}_2$; its rounded relative molecular mass of 88 predicts an air-relative vapor density of approximately $88/28.97=3.04$, close to 3.05. If the stated vapor density were instead relative to hydrogen, it would imply a relative molecular mass near 6.1, smaller than the empirical formula mass and incompatible with the analysis. That interpretation cannot describe a pure, undecomposed molecular vapor with the stated composition.

Under the older equivalent weight convention $\mathrm{C}=6$, $\mathrm{O}=8$, $\mathrm{H}=1$, the same composition and formula weight could be written ${\mathrm{C}}_8{\mathrm{H}}_8{\mathrm{O}}_4$. This is a change of notation, not eight modern carbon chemical atoms in the molecule. The result specifies composition and molar mass; it does not distinguish among structural isomers, such as ethyl acetate and butyric acid.