Chemistry 9701 · AS & A Level · Atoms, molecules and stoichiometry

Atoms, molecules and stoichiometry — practice question

The compound trans-4-hydroxy-2-nonenal (HNE) is believed to cause lung infections when cigarettes are smoked. Its structural formula is shown, matching CH$_3$(CH$_2$)$_4$CH(OH)CH=CHCHO.
(a)[1]

What is the empirical formula for trans-4-hydroxy-2-nonenal?

(b(i))[2]

HNE contains an alkene group. Name, as fully as possible, two other functional groups found in the HNE molecule.

(b(ii))[3]

How could you confirm that the alkene group is present in HNE? State the reagent used and the observation you would make.

(c(i))[2]

HNE is a reactive compound. Give the structural formulae of every carbon-containing compound formed when HNE is reacted with hot concentrated manganate(VII) ions in acid solution.

(c(ii))[1]

HNE is reacted with hot phosphorus trichloride, PCl$_3$. Give the structural formulae of every carbon-containing compound formed.

(c(iii))[1]

HNE is reacted with sodium tetrahydridoborate(III), NaBH$_4$. Give the structural formulae of every carbon-containing compound formed.

Worked solution & mark scheme

This 10-mark question has a full step-by-step worked solution and mark scheme. One marking point: Correct molecular formula given as $\mathrm{C_9H_{16}O_2}$

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