Chemistry 9701 · AS & A Level · Hydroxy compounds

Hydroxy compounds — practice question

Naturally occurring organic compounds often contain oxygen. They may include alcohol, aldehyde, carboxylic acid, ester or ketone functional groups. These functional groups can be recognised by how they react with particular reagents. Compound F is a white solid with molecular formula $\text{C}_3\text{H}_6\text{O}_3$. F dissolves in water. When $\text{NaHCO}_3$ is added to this solution, a colourless gas, G, is released and it turns limewater milky.
(a(i))

Which gas is G?

(a(ii))[2]

Which functional group is revealed by this test in F?

(b(i))

F is heated with concentrated sulfuric acid to give a colourless liquid H. When cold dilute acidified $\text{KMnO}_4$ is shaken with H, the solution becomes colourless. What type of reaction produces H from F?

(b(ii))[4]

Use your answers to a(ii) and b(i) to deduce the structural formula of the colourless liquid H.

(c)[4]

Compound $F$ reacts with sodium. Calculate the volume of $\text{H}_2$, measured at room temperature and pressure, produced when $0.600\,\text{g}$ of $F$ is reacted with an excess of Na.

(d(i))

There are two structural isomers of $F$ that produce the reactions described in (a) and (b). Suggest two structural formulae for these isomers.

(d(ii))[2]

Isomers $J$ and $K$ can both be oxidised. What is produced when each of the isomers $J$ and $K$ is heated under reflux with acidified $\text{K}_2\text{Cr}_2\text{O}_7$?

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