Chemistry 9701 · AS & A Level · Reaction kinetics

Reaction kinetics — practice question

Phenacyl chloride has served as one ingredient in certain tear gases. Its lachrymatory and irritant effects arise because it reacts with water in body tissues, generating hydrochloric acid. It takes part in a nucleophilic substitution reaction with $\text{NaOH(aq)}$.
(a)[2]

Enter the formulae of the products from this reaction in the two boxes above.

(b(i))

What does the term order of reaction mean?

(b(ii))

Deduce the order with respect to each reactant from the data above. Explain how you reached your answer.

(b(iii))

Write the overall rate equation for this reaction.

(b(iv))[7]

Describe a mechanism for this reaction that fits the overall rate equation. Show every intermediate and/or transition state, include partial charges, and use curly arrows to show the movement of electron pairs.

(c(i))

Describe an experiment that would demonstrate that $\text{CH}_3\text{COCl}$ reacts with water far more quickly than phenacyl chloride. State the reagents you would use, and the observations you would record for each chloride.

(c(ii))[4]

Suggest why there is this difference in reactivity.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Main product identified as $\mathrm{C_6H_5COCH_2OH}$ or $\mathrm{C_8H_8O_2}$

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