Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Benzoyl chloride, $\text{C}_6\text{H}_5\text{COCl}$, can be prepared from ethyl benzene by means of a two-step route. A reaction scheme is provided.
(a(i))[1]

Draw the intermediate organic compound $M$ in the box.

(a(ii))[2]

Suggest appropriate reagents and conditions for step 1 and step 2. step 1 ................................................................. step 2 .................................................................

(a(iii))[2]

Identify the reaction type in step 1 and step 2. step 1 ................................................................. step 2 .................................................................

(b(i))[4]

$\text{C}_6\text{H}_5\text{COCl}$ reacts with phenol, $\text{C}_6\text{H}_5\text{OH}$, to produce the ester phenyl benzoate, $\text{C}_6\text{H}_5\text{COOC}_6\text{H}_5$. Complete the mechanism in Fig. 9.1 and 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.

(b(ii))[1]

Name this mechanism in full.

(c)[3]

Benzoyl chloride, chlorobenzene and chloroethane are hydrolysed at different rates when each compound is added separately to water at $25\,^{\circ}\text{C}$. Suggest the relative ease of hydrolysis of these three compounds. Explain your answer. hardest to hydrolyse ........................................ easiest to hydrolyse explanation .................................................................

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Benzoic acid structure shown as M

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