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

Carboxylic acids and derivatives — practice question

Food additives are substances mixed into food to preserve flavour or improve taste and appearance. European Union law requires most additives used in foods to be labelled clearly in the ingredients list, either by name or by an ‘E number’. E296 is malic acid, which is found in unripe fruit. Malic acid has the structural formula $\text{HO}_2\text{CCH}_2\text{CH(OH)CO}_2\text{H}$.
(a)[6]

The reactions of malic acid are illustrated below. In the boxes below, write the structural formulae of organic compounds A to F.

(b)[3]

What reaction type is shown by each conversion below? malic acid into C C into D C into E

(c)[1]

Suggest one major commercial use of compounds such as A or B.

(d(i))[3]

Malic acid is chiral. Draw fully displayed formulae of the two optical isomers of malic acid. Mark the chiral carbon atom with an asterisk $(*)$.

(d(ii))[3]

Compound C also exhibits stereoisomerism. Draw the skeletal formulae of each stereoisomer of C. Label each isomer.

(e)[3]

The food additive E330 is another organic compound that occurs naturally in fruit. E330 has the following composition by mass: C, $37.5\%$; H, $4.17\%$; O, $58.3\%$. Calculate the empirical formula of E330.

Worked solution & mark scheme

This 19-mark question has a full step-by-step worked solution and mark scheme. One marking point: Accurate structures for A-F, as shown in the scheme

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