Chemistry 9701 · AS & A Level · Nitrogen compounds

Nitrogen compounds — practice question

Valinol may be made by the reactions shown below, with valine serving as the starting material in reaction 1.
(a(i))[1]

Write an equation for reaction 1, using $[\text{H}]$ to indicate the reducing agent.

(a(ii))[1]

Suggest a reagent that would be suitable for reaction 1.

(a(iii))[1]

State the mechanism for reaction 2.

(b)[2]

Valine and glycine, $\text{H}_2\text{NCH}_2\text{COOH}$, make the tripeptide Gly-Val-Gly. Draw the structure of this tripeptide. Show the peptide bonds fully displayed.

(c(i))[2]

Valine exists as two stereoisomers. Draw three-dimensional diagrams to show the two stereoisomers of valine. In your diagrams, the $-\text{CH}(\text{CH}_3)_2$ group can be represented by -R. State the type of stereoisomerism shown.

(c(ii))[1]

Valine is an amino acid. Draw valine in zwitterion form.

(c(iii))[1]

Valinate, $\text{Val}^-$, is the anion of valine. It participates in a ligand substitution reaction with hexaaquanickel(II) ions, and complex $Z$ is produced. $\left[\text{Ni}(\text{H}_2\text{O})_6\right]^{2+}(aq) + 2\text{Val}^-(aq) \rightleftharpoons \left[\text{Ni}(\text{H}_2\text{O})_2(\text{Val})_2\right](aq) + 4\text{H}_2\text{O}(l)$. Write an expression for $K_{\text{stab}}$ for this equilibrium.

(c(iv))[1]

At room temperature, the numerical value of $K_{\text{stab}}$ is $2.34 \times 10^5$. Explain what this value shows about the equilibrium and the stability of complex $Z$.

(c(v))[1]

$Z$ is an octahedral complex with formula $\left[\text{Ni}(\text{H}_2\text{O})_2(\text{Val})_2\right]$. Use this information to state the type of ligand that the valinate ion is acting as in this complex.

(iii)[1]

Valinate, $\text{Val}^-$, is the anion of valine and it undergoes ligand substitution with hexaaquanickel(II) ions to form complex $Z$. $$[\text{Ni}(\text{H}_2\text{O})_6]^{2+}(aq) + 2\text{Val}^-(aq) \rightleftharpoons [\text{Ni}(\text{H}_2\text{O})_2(\text{Val})_2](aq) + 4\text{H}_2\text{O}(l)$$ Write an expression for $K_{\text{stab}}$ for this equilibrium.

(iv)[1]

At room temperature, the numerical value of $K_{\text{stab}}$ is $2.34 \times 10^5$. Explain what this value shows about the equilibrium and the stability of complex $Z$.

(v)[1]

$Z$ is an octahedral complex with formula $[\text{Ni}(\text{H}_2\text{O})_2(\text{Val})_2]$. Use this information to state the type of ligand that the valinate ion is acting as in this complex.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Reduction of amino acid to amino alcohol using $[H]$

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