Chemistry 9701 · AS & A Level · Analytical techniques

Analytical techniques — practice question

Alanine, $\text{H}_2\text{NCH}(\text{CH}_3)\text{CO}_2\text{H}$, together with glutamic acid, $\text{H}_2\text{NCH}(\text{CH}_2\text{CH}_2\text{CO}_2\text{H})\text{CO}_2\text{H}$, are both amino acids that occur naturally.
(a)[2]

The compound $\text{H}_2\text{NCH}(\text{CH}_3)\text{CO}_2\text{H}$ occurs as two optical isomers. Draw three-dimensional representations of these two optical isomers.

(b)[3]

A proton ($^1\text{H}$) NMR spectrum of either alanine in $\text{D}_2\text{O}$ or glutamic acid in $\text{D}_2\text{O}$ is shown. State whether the spectrum is that of alanine in $\text{D}_2\text{O}$ or glutamic acid in $\text{D}_2\text{O}$. Explain your answer with reference to the number of peaks and the splitting patterns.

(c)

The mass spectrum for glutamic acid, $\text{H}_2\text{NCH}(\text{CH}_2\text{CH}_2\text{CO}_2\text{H})\text{CO}_2\text{H}$, is recorded.

(c(i))[1]

State the $m/e$ value for the molecular ion peak in this spectrum.

(c(ii))[2]

The spectrum contains peaks at $m/e$ values of $88$ and $131$. Draw the structures of the ions that produce these peaks.

(d)

At $\text{pH }11$, alanine is present as $\text{H}_2\text{NCH}(\text{CH}_3)\text{CO}_2^-$ ions and glutamic acid is present as $\text{H}_2\text{NCH}(\text{CH}_2\text{CH}_2\text{CO}_2^-)\text{CO}_2^-$ ions. A mixture of alanine and glutamic acid at $\text{pH }11$ is then subjected to electrophoresis.

(d(i))[1]

State how the mixture can be kept at $\text{pH }11$ while electrophoresis is carried out.

(d(ii))[2]

Draw a fully labelled diagram of the apparatus used to carry out this electrophoresis. Your diagram should show where the alanine and glutamic acid mixture is placed at the start of the experiment.

(d(iii))[1]

Identify which electrode each amino acid moves towards during electrophoresis at $\text{pH } 11$. Alanine \dotfill\, Glutamic acid \dotfill

(d(iv))[2]

In one electrophoresis experiment at $\text{pH } 11$, glutamic acid moves $3.4\,\text{cm}$. Alanine moves a shorter distance. Explain the reasons for the difference in the distances travelled.

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