Chemistry 9701 · AS & A Level · 7.5

7.5 — practice question

Asparagine and aspartic acid are two amino acids found naturally. Table 8.1 shows their structures and isoelectric points.
(a)[1]

Define the term isoelectric point.

(b)[2]

At pH 2, draw the structures of asparagine and aspartic acid.

(c)[2]

Asparagine and aspartic acid are each treated separately with excess $\mathrm{LiAlH_4}$. Draw the structures of the organic products formed in these reactions.

(d(i))[1]

Propanedioic acid, $\mathrm{HOOCCH_2COOH}$, is treated with excess thionyl chloride, $\mathrm{SOCl_2}$. Propanedioyl chloride, $\mathrm{ClOCCH_2COCl}$, is produced. Write an equation for this reaction.

(d(ii))[2]

Propanedioyl chloride reacts with excess asparagine to give compound G with molecular formula $\mathrm{C_{11}H_{16}N_4O_8}$. Each molecule of compound G contains four amide groups. Draw the structure of compound G.

(e)[2]

Asparagine is hydrolysed with excess hot $\mathrm{NaOH(aq)}$. Draw the structure of the organic product of this reaction.

(f)[3]

A polymer may be made from asparagine, $\mathrm{HOOCCH(NH_2)CH_2CONH_2}$, using this as the only monomer. Draw a section of the polymer chain containing three monomer residues. Clearly indicate the repeat unit of the polymer on your diagram.

(g(i))[2]

Aspartic acid has two optically active forms. Plane polarised light is passed through pure samples of these two optically active forms in solutions of the same concentration. Describe two similarities and one difference in their effect on the plane polarised light.

(g(ii))[1]

State the term for a mixture that contains equal amounts of the two optically active forms.

Worked solution & mark scheme

This 16-mark question has a full step-by-step worked solution and mark scheme. One marking point: the pH at which an amino acid is present as a zwitterion

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