Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

(a) Methylbenzene reacts readily with nitronium ions, $\text{NO}_2^+$. These $\text{NO}_2^+$ ions are produced when concentrated nitric acid reacts with concentrated sulfuric acid.
(a(i))[1]

Write an equation showing how the $\text{NO}_2^+$ ion is formed.

(a(ii))[3]

Complete the mechanism in Fig. 6.1 for the nitration of methylbenzene to make 1-methyl-2-nitrobenzene. Include every relevant curly arrow and charge.

(b)[2]

Phenol can be nitrated with dilute nitric acid. Explain why the nitration of phenol occurs under milder conditions than the nitration of benzene.

(c)[1]

A sample of 2-nitrophenol is treated with sodium. Complete the equation in Fig. 6.2 for the reaction of 2-nitrophenol with sodium.

(d(i))[1]

Suggest the reagents and conditions for reaction 1 shown in Fig. 6.3.

(d(ii))[1]

Name the reaction type for reaction 1.

(d(iii))[1]

Reaction 2 takes place at room temperature. Draw the structure of the organic product from reaction 2 in Fig. 6.3.

(d(iv))[1]

Name the mechanism operating in reaction 2.

(e)[4]

The $\text{NO}_2$ group in 2-nitrophenol acts as an electron‑withdrawing group. Suggest the relative acidities of ethanol, 2-nitrophenol, phenol and water. Explain your answer.

(f(i))[2]

Name and classify the three remaining functional groups in salbutamol in Table 6.1.

(f(ii))[1]

Salbutamol reacts with $\text{Br}_2(aq)$ to produce organic product X. Draw the structure of X.

(f(iii))[1]

When salbutamol reacts with excess $\text{SOCl}_2$, organic product Y is formed. The molecular formula of Y is $\text{C}_{13}\text{H}_{19}\text{Cl}_2\text{NO}$. Draw the structure of Y.

Worked solution & mark scheme

This 19-mark question has a full step-by-step worked solution and mark scheme. One marking point: Production of $\mathrm{NO_2^+}$ from nitric acid and sulfuric acid

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