Chemistry 9701 · AS & A Level · Analytical techniques

Analytical techniques — practice question

Thin-layer chromatography can be used to separate amino acids. This method is applied to analyse a mixture of amino acids.
(a(i))[1]

Using the chromatogram together with the $R_f$ values, deduce which amino acid gives spot A and which gives spot B.

(a(ii))[1]

A second chromatogram of the same mixture is run with a more polar solvent. Predict how the $R_f$ values of the amino acids change, and explain why.

(b(i))[2]

Complete the equations to illustrate the acid-base behaviour of glycine, $\text{H}_2\text{NCH}_2\text{CO}_2\text{H}$.\n\n$\text{H}_2\text{NCH}_2\text{CO}_2\text{H}$(aq) $+$ $\text{HCl}$(aq) $\rightarrow$ \n\n$\text{H}_2\text{NCH}_2\text{CO}_2\text{H}$(aq) $+$ $\text{NaOH}$(aq) $\rightarrow$

(b(ii))[2]

In aqueous solution, amino acids are present as zwitterions. Draw the zwitterionic structure of glycine and explain how glycine’s zwitterion is formed.

(c)[1]

Except for glycine, every naturally occurring amino acid has a chiral centre and shows stereoisomerism. Draw the two stereoisomers of alanine, $\text{CH}_3\text{CH(NH}_2\text{)CO}_2\text{H}$.

(d(i))[2]

Alanine can be prepared from 2-chloropropanoic acid, $\text{CH}_3\text{CHClCO}_2\text{H}$. State the reagents and conditions, and name the mechanism for this reaction.

(d(ii))[3]

State and explain the order of acidity for trichloroethanoic acid, chloroethanoic acid and ethanoic acid.

(e)[3]

Serine, $\text{HOCH}_2\text{CH(NH}_2\text{)CO}_2\text{H}$, may react with alanine, $\text{CH}_3\text{CH(NH}_2\text{)CO}_2\text{H}$, to give three different structural isomers, each with molecular formula $\text{C}_6\text{H}_{12}\text{N}_2\text{O}_4$. Draw the structures of these three structural isomers.

Worked solution & mark scheme

This 15-mark question has a full step-by-step worked solution and mark scheme. One marking point: $A=$ leucine; $B=$ glutamic acid

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