Chemistry 9701 · AS & A Level · Carboxylic acids and derivatives

Carboxylic acids and derivatives — practice question

Compound $X$ has the same functional groups as citric acid. The table sets out a few similarities and differences between citric acid and compound $X$.
(a)[3]

Complete the equation to show how excess sodium reacts with citric acid. Show the product as a skeletal structure.

(b(i))[2]

Use the information in the table to work out the skeletal formula of $X$, $\text{C}_3\text{H}_6\text{O}_3$. Draw the skeletal formula of $X$ in the box. Label the chiral centre of compound $X$ with an asterisk ($^*$).

(b(ii))[2]

Explain why compound $X$ is oxidised by acidified $\text{Cr}_2\text{O}_7^{2-}$ whereas citric acid is not.

(c)[2]

Compound $X$ belongs to one of a pair of stereoisomers. Stereoisomerism arises when a molecule has at least one of two key features. State the two key features that give rise to stereoisomerism.

(d)[1]

A structural isomer of compound $X$ does not fizz when it is added to sodium. Explain what is meant by structural isomer.

Worked solution & mark scheme

This 10-mark question has a full step-by-step worked solution and mark scheme. One marking point: the three COOH groups all convert to $\mathrm{COO^-Na^+}$

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