Chemistry 9701 · AS & A Level · Nitrogen compounds

Nitrogen compounds — practice question

(a)[4]

Give the reactants and conditions for two separate reaction types that each yield diethylamine, $\text{CH}_3\text{CH}_2\text{NHCH}_2\text{CH}_3$. reaction one: reaction two:

(b)[3]

Describe how the basicities of diethylamine, phenylamine and ammonia compare in aqueous solution, and explain your answer using structure. Say which is least basic and which is most basic.

(c)[2]

Phenylamine reacts with $\text{HNO}_2\text{(aq)}$ at $4^{\circ}\text{C}$ to form compound $\text{P}$. Compound $\text{P}$ then reacts with phenol in alkaline conditions at $4^{\circ}\text{C}$. After this reaction, the product is acidified to give azo compound $\text{Q}$. Draw the structure of $\text{Q}$. Circle the azo group in your drawing. State one use of an azo compound such as $\text{Q}$.

(d(i))[4]

$\text{CH}_3\text{CH}_2\text{NHCH}_2\text{CH}_3$ reacts with ethanoyl chloride, $\text{CH}_3\text{COCl}$, to produce the amide N,N-diethylethanamide, $\text{CH}_3\text{CON(C}_2\text{H}_5)_2$. Figure 9.1 shows an incomplete account of the mechanism for this reaction. Complete the mechanism in Fig. 9.1. You should include: • every relevant dipole ($\delta^+$ and $\delta^-$) and full electric charge ($+$ and $-$) on the species in box one and in box two • every relevant lone pair on the species in box one and in box two • every relevant curly arrow to show electron-pair movement in box one and in box two • the formula of the second product in box three.

(d(ii))[1]

Name the mechanism.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Ethylamine with chloroethane

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