Chemistry 9701 · AS & A Level · Carbonyl compounds

Carbonyl compounds — practice question

Modern telescopes have enabled astronomers to detect many molecules within dust clouds in space. Hydroxyethanal, $\text{HOCH}_2\text{CHO}$, is one molecule that has been identified.
(a(i))

Hydroxyethanal has two functional groups. Name, as fully as you can, each functional group present in hydroxyethanal.

(a(ii))[7]

For each functional group, identify a reagent that reacts with that group but does not react with the other functional group present. For each case, describe what would be seen during the reaction.

(b(i))

Give the skeletal formula of the organic compound produced when hydroxyethanal is reacted separately with $\text{NaBH}_4$.

(b(ii))[2]

Give the skeletal formula of the organic compound produced when hydroxyethanal is reacted with $\text{Cr}_2\text{O}_7^{2-}/\text{H}^+$ under reflux conditions.

(c(i))

In the boxes below, draw the structural formula of your proposed intermediates $X$ and $Y$ for the conversion of hydroxyethanal into aminoethanoic acid.

(c(ii))[5]

State the reagents for each of the three steps you have selected in this conversion.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Functional group identified as primary alcohol, not hydroxyl

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