Chemistry 9701 · AS & A Level · Nitrogen compounds

Nitrogen compounds — practice question

Ethylamine and phenylamine belong to the class of primary amines.
(a(i))[1]

Ethylamine is produced when ethanamide, $\text{CH}_3\text{CONH}_2$, undergoes reduction by $\text{LiAlH}_4$. Write an equation for this reaction. Use [H] to represent one atom of hydrogen from the reducing agent.

(a(ii))[2]

Ethylamine is formed in the reaction of bromoethane with ammonia. Name the mechanism of this reaction and state the conditions used.

(a(iii))[1]

The reaction in (a)(ii) also produces secondary and tertiary amines. Suggest the identity of a secondary or tertiary amine formed in reaction (a)(ii).

(b)[4]

Ethylamine is a weak base. State the relative basicities of ammonia, ethylamine and phenylamine. Explain your answer.

(c)[3]

Pure phenylamine, $\text{C}_6\text{H}_5\text{NH}_2$, can be made from benzene in two steps. Draw the structure of the intermediate compound. Suggest reagents and conditions for each step.

(d)

Fig. 4.2 shows several reactions of phenylamine.

(d(i))[1]

Draw the structure of $\mathrm{W}$, the organic product of reaction 1.

(d(ii))[1]

State the reagents used in reaction 2.

(d(iii))[1]

Benzenediazonium chloride, $\mathrm{C_6H_5N_2Cl}$, and $\mathrm{X}$ react together in reaction 4 to form $\mathrm{Y}$, an azo compound. Name $\mathrm{X}$, the organic product of reaction 3.

(d(iv))[1]

State the necessary conditions for reaction 4 to occur.

(d(v))[1]

Suggest a use for $\mathrm{Y}$.

(e(i))[2]

Methylamine, $\mathrm{CH_3NH_2}$, is another primary amine. $\mathrm{CH_3NH_2}$ can act as a monodentate ligand. Define monodentate ligand.

(e(ii))[2]

$\mathrm{Cu^{2+}(aq)}$ reacts with $\mathrm{CH_3NH_2}$ to form $[\mathrm{Cu(CH_3NH_2)_2(H_2O)_4}]^{2+}$. Draw three-dimensional diagrams to show the two geometrical isomers of $[\mathrm{Cu(CH_3NH_2)_2(H_2O)_4}]^{2+}$.

(e(iii))[1]

State the coordination number of copper in $[\mathrm{Cu(CH_3NH_2)_2(H_2O)_4}]^{2+}.

(f(i))[1]

$\mathrm{Cd^{2+}(aq)}$ ions form tetrahedral complexes with $\mathrm{CH_3NH_2}$, $\mathrm{OH^-}$ and $\mathrm{Cl^-}$ ions, as shown in equilibria 1, 2 and 3. Equilibrium 1: $\mathrm{Cd^{2+}(aq) + 4CH_3NH_2(aq) \rightleftharpoons [Cd(CH_3NH_2)_4]^{2+}(aq)}$, $K_{\text{stab}} = 3.3 \times 10^6$ Give the units of $K_{\text{stab}}$ for equilibrium 1.

(f(ii))[1]

Equilibrium 3: $\mathrm{Cd^{2+}(aq) + 4Cl^-(aq) \rightleftharpoons CdCl_4^{2-}(aq)}$ Write an expression for $K_{\text{stab}}$ for equilibrium 3.

(f(iii))[1]

A solution of $\text{Cl}^-(aq)$ is added to $\text{Cd}^{2+}(aq)$ and allowed to reach equilibrium. The equilibrium concentrations are given: $[\text{Cd}^{2+}(aq)] = 0.043\,\text{mol dm}^{-3}$ and $[\text{Cl}^-(aq)] = 0.072\,\text{mol dm}^{-3}$. Use your expression in f(ii) to calculate the concentration of $[\text{CdCl}_4]^{2-}(aq)$ in the equilibrium mixture.

(f(iv))[1]

When $\text{CH}_3\text{NH}_2(aq)$ is added to $\text{Cd}^{2+}(aq)$, a mixture of $[\text{Cd}(\text{CH}_3\text{NH}_2)_4]^{2+}(aq)$ and $[\text{Cd}(\text{OH})_4]^{2-}(aq)$ forms. Suggest how the $[\text{Cd}(\text{OH})_4]^{2-}(aq)$ is formed.

(f(v))[2]

$\text{Cd}^{2+}(aq)$ exists as a complex ion, $[\text{Cd}(\text{H}_2\text{O})_6]^{2+}(aq)$. Identify the most stable and the least stable of the complexes in Table 4.1 by placing one tick ($\checkmark$) in each column. Explain your answer.

Worked solution & mark scheme

This 27-mark question has a full step-by-step worked solution and mark scheme. One marking point: $CH_3CONH_2 + 4[H] \rightarrow CH_3CH_2NH_2 + H_2O$

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