Chemistry 9701 · AS & A Level · Hydrocarbons

Hydrocarbons — practice question

Table 6.1 shows the reagents and conditions needed for nitration of benzene, benzoic acid and phenol. Concentrated $\text{HNO}_3$ reacts with concentrated $\text{H}_2\text{SO}_4$ to form the electrophile $\text{NO}_2^+$.
(a(i))[3]

Complete Fig. 6.1 by showing the mechanism for the reaction of benzene with $\text{NO}_2^+$. Include every relevant curly arrow and charge.

(a(ii))[1]

Write the equation that shows the regeneration of $\text{H}_2\text{SO}_4$.

(b)[2]

Draw the chief products formed when benzoic acid and phenol undergo mononitration.

(c)[4]

Compare how readily benzene, benzoic acid and phenol undergo nitration. Justify your answer by referring to the structures of the three compounds.

(d(i))[3]

Suggest the structures of compounds $X$, $Y$ and $Z$, and place them in the boxes in Fig. 6.2. In step 3, compound $Y$ reacts with compound $Z$, and compound $Z$ is prepared from compound $X$. Assume that the $-\text{SO}_3^-\text{Na}^+$ groups do not react.

(d(ii))[3]

State the reagents and conditions for step 1 and step 2.

Worked solution & mark scheme

This 16-mark question has a full step-by-step worked solution and mark scheme. One marking point: curly arrow from the ring to $NO_2^+$

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