Chemistry 9701 · AS & A Level · 8.2

8.2 — practice question

When arenes undergo electrophilic substitution, different substituents may steer incoming groups to different ring positions. Making carbon-carbon bonds is an important part of organic synthesis. Fig. 8.1 illustrates the two-step preparation of compound Q from benzene.
(a(i))[1]

Describe the directing effect shown by the $-\mathrm{NO}_2$ group. Explain your answer.

(a(ii))[1]

In the nitration of arenes, a mixture of concentrated $\mathrm{HNO}_3$ and concentrated $\mathrm{H}_2\mathrm{SO}_4$ is used to produce the $\mathrm{NO_2^+}$ electrophile. Write an equation for the formation of the $\mathrm{NO_2^+}$ electrophile.

(b(i))[1]

In Fig. 8.1, draw the structure of compound P in the box.

(b(ii))[2]

Suggest reagents and conditions for reactions 1 and 2 in Fig. 8.1. For reaction 1, give reagents and conditions. For reaction 2, give reagents and conditions.

(c)[3]

Separate samples of $\text{C}_6\text{H}_5\text{Br}$ and $\text{C}_6\text{H}_5\text{CH}_2\text{Br}$ are each added to warm $\text{AgNO}_3\text{(aq)}$. State the observations, if any, and explain your answer. $\text{C}_6\text{H}_5\text{Br}$ with $\text{AgNO}_3\text{(aq)}$ $\text{C}_6\text{H}_5\text{CH}_2\text{Br}$ with $\text{AgNO}_3\text{(aq)}$ explanation

(d(i))[1]

Acyl bromides, $\text{RCOBr}$, react readily with $\text{H}_2\text{O}$. The mechanism for this reaction is similar to the one for the reaction of $\text{H}_2\text{O}$ with acyl chlorides, $\text{RCOCl}$. Name the mechanism of this reaction.

(d(ii))[4]

Complete the mechanism in Fig. 8.2 for the reaction of $\text{RCOBr}$ with $\text{H}_2\text{O}$. Include all relevant lone pairs of electrons, curly arrows, charges and dipoles. Draw the structure of the intermediate.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\mathrm{NO}_2$ group directs to 3 (and 5) / meta position AND because it is an electron-withdrawing / electronegative group

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