Fig. 6.1 shows two reactions of ethanedioic acid, HOOCCOOH. [Figure 6.1]
- (a)(i)Draw the organic product G in the box in Fig. 6.1.[1]
- (a)(ii)In Fig. 6.1, SOCl₂ is given as the reagent that reacts with HOOCCOOH to produce G. Identify a different reagent that also reacts with HOOCCOOH to produce G.[1]
- (b)Identify two different reagents that oxidise HOOCCOOH to form carbon dioxide and water.[2]
- (c)HOOCCOOH ionises as shown. HOOCCOOH ⇌ HOOCCOO⁻ + H⁺ HOOCCOOH is a much stronger acid than methanoic acid, HCOOH. Suggest an explanation for this difference in acidity.[2]
- (d)(i)Benzene-1,4-dicarboxylic acid, HOOCC₆H₄COOH, can be made from benzene, C₆H₆, in two steps as shown in Fig. 6.2. [Figure 6.2] Suggest the identity of J by drawing its structure in the box in Fig. 6.2.[1]
- (d)(ii)Identify the reagents and conditions for step 1 and step 2. step 1 step 2[2]
- (d)(iii)Draw the structure of exactly one repeat unit of the polymer formed when benzene-1,4-dicarboxylic acid reacts with ethane-1,2-diol, HOCH₂CH₂OH. The linkage formed between the monomers should be shown fully displayed.[2]
- (d)(iv)State the type of polymerisation that occurs when benzene-1,4-dicarboxylic acid reacts with ethane-1,2-diol and name the linkage formed between the monomers. type of polymerisation linkage[1]
This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.
Mark scheme
Marking points from the official mark scheme (Oct/Nov 2024). The mark or mark type is shown in brackets.
- [1] ClOCCOCl
- [1] PCl₃ / PCl₅
- [1] oxygen
- [1] acidified KMnO₄
- [1] C=O are electron withdrawing / electronegative
- [1] weakens O-H bond OR stabilises anion
- [1] H₃C-C₆H₄-CH₃
- [1] step 1: CH₃Cl + AlCl₃
- [1] step 2: hot alkaline KMnO₄
- [1] correctly displayed ester linkage
- [1] rest of structure
- [1] condensation AND ester
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