Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Benzene may be converted into benzoic acid by the two-stage route shown in Fig. 7.1.
(a)[2]

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

(b)[2]

Use Table 7.1 to complete the two sentences so that they describe these two spectra. The carbon ($^{13}\text{C}$) NMR spectrum of methylbenzene: • shows .............. peak(s) in the chemical shift range of .............. and • shows .............. peak(s) in the chemical shift range of .............. . The carbon ($^{13}\text{C}$) NMR spectrum of benzoic acid: • shows .............. peak(s) in the chemical shift range of .............. and • shows .............. peak(s) in the chemical shift range of .............. .

(c(i))[4]

Under suitable conditions, methylbenzene reacts with $\text{Cl}_2$ to form compound J. Under different conditions and with different reagents, methylbenzene reacts with $\text{Cl}_2$ to form compound K. Suggest and draw the structures of compounds J and K in the boxes. The molecular formula of each compound is given. State the reagents and conditions needed to form each product.

(c(ii))[3]

Under suitable conditions with a chlorine-containing reagent, benzoic acid forms compound L. Under different conditions with a different chlorine-containing reagent, benzoic acid forms compound M. Suggest and draw the structures of compounds L and M in the boxes. The molecular formula of each product is given. State the reagents and conditions needed to prepare compound M from benzoic acid.

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This 11-mark question has a full step-by-step worked solution and mark scheme. One marking point: $\mathrm{CH_3Cl}$ with $\mathrm{AlCl_3}$

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