Chemistry 9701 · AS & A Level · Carboxylic acids and derivatives

Carboxylic acids and derivatives — practice question

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

Draw the organic intermediate $\text{M}$ in the box.

(a(ii))[2]

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

(a(iii))[2]

Identify the reaction type in step 1 and 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 form the ester phenyl benzoate, $\text{C}_6\text{H}_5\text{COOC}_6\text{H}_5$. Finish the mechanism in Fig. 9.1 and show: • all relevant dipoles ($\delta^+$ and $\delta^-$) together with full electric charges ($+$ and $-$) on the species in box one and in box two • all relevant lone pairs on the species in box one and in box two • all relevant curly arrows to illustrate electron-pair movement in box one and in box two • the formula of the second product in box three.

(b(ii))[1]

Name the reaction mechanism.

(c)[3]

Benzoyl chloride, chlorobenzene and chloroethane show different hydrolysis rates when each one is added separately to water at $25\,^{\circ}\text{C}$. Suggest their relative ease of hydrolysis. Explain your answer.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Accurate structure of M (benzoic acid)

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