Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Ethanedioyl dichloride, $\text{ClCOCOCl}$, is a valuable reagent in organic synthesis. It can be prepared from compound A in one step.
(a(i))[1]

Use the box to suggest compound A by drawing its structure.

(a(ii))[1]

State the reagents and conditions required to convert A into $\text{ClCOCOCl}$.

(b(i))[4]

Use the boxes to suggest the identities of compounds B-E by drawing their structures.

(b(ii))[5]

State the reagents and conditions for these steps: step 1; step 3; step 4; step 6.

(b(iii))[1]

When the amount of $\text{ClCOCOCl}$ used in step 2 is reduced, a different compound is produced in step 2 with the molecular formula $\text{C}_{14}\text{H}_8\text{O}_2\text{Cl}_2$. Suggest the structure of this compound.

(b(iv))[1]

Identify the steps in the synthesis of Q from benzene that are electrophilic substitution reactions.

(c)[4]

Draw the structures of the compounds formed when Q is treated with each reagent below. If there is no reaction, write ‘no reaction’ in the box: • heat with $\text{Cr}_{2}\text{O}_{7}^{2-}/\text{H}^{+}(aq)$ • heat with $\text{NaOH}(aq)$ • $\text{Br}_{2}(aq)$ • $\text{HCl}(aq)$ at room temperature

Worked solution & mark scheme

This 17-mark question has a full step-by-step worked solution and mark scheme. One marking point: Either $HO_2C-CO_2H$ or $HO_2C-COCl$

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