State the relative acidities of bromoethanoic acid, BrCH2COOH, chloroethanoic acid, ClCH2COOH, ethanoic acid, CH3COOH and ethanol, CH3CH2OH. Explain your answer. most acidic __________________________________ least acidic __________________________________ [4]
- (a)State the relative acidities of bromoethanoic acid, BrCH2COOH, chloroethanoic acid, ClCH2COOH, ethanoic acid, CH3COOH and ethanol, CH3CH2OH. Explain your answer. most acidic __________________________________ least acidic __________________________________ [4][4]
- (b)Fig. 7.1 shows the reaction of methylbenzene and ethanedioic acid with KMnO4. Predict the major carbon-containing product for each of these reactions. [Figure 7.1] [2][2]
- (c)(i)Polyamide X can be synthesised from ethanedioic acid and benzene-1,4-diamine. [Structure of benzene-1,4-diamine] Draw the repeat unit of polyamide X in the box. The new functional group formed should be shown displayed. [Box for polyamide X] [2][2]
- (c)(ii)Benzene-1,4-diamine can be formed by reduction of 1,4-dinitrobenzene. Complete the equation for this reduction. [H] represents one atom of hydrogen from a reducing agent. [Equation to complete] [1][1]
- (d)(i)Fig. 7.2 shows the two-step synthesis of the azo compound W. [Figure 7.2] Suggest structures for compounds V and W and draw them in the boxes in Fig. 7.2.[2]
- (d)(ii)Give the reagents and conditions for step 1.[1]
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Mark scheme
Marking points from the official mark scheme (Oct/Nov 2025). The mark or mark type is shown in brackets.
- [1] M1: ClCH2COOH BrCH2COOH CH3COOH CH3CH2OH most acidic least acidic
- [1] M2: electron withdrawing groups / electronegative groups / negative inductive effect AND weakens O-H bond / more stable anion OR electron donating groups / positive inductive effect AND strengthens O-H bond / less stable anion
- [1] M3 M4: chlorine is more electron-withdrawing / electronegative than bromine (related to XCH2COOH)
- [1] M3 M4: electron withdrawing of C=O / negative inductive effect of C=O (related to COOH)
- [1] M3 M4: positive inductive effect / electron donating of alkyl / ethyl / R group (related to ROH)
- [any two [1], all three [2]]
- [1] M1: Benzoic acid structure (PhCOOH)
- [1] M2: CO2
- [1] M1: correct displayed amide bond with C=O, (C6H5)–N and (C−)C=O
- [1] M2: rest of the structure correct with continuation bonds
- [1] O2N-C6H4-NO2 + 12[H] → H2N-C6H4-NH2 + 4H2O
- [1] M1: (structure of benzenediazonium chloride: C6H5N2+Cl-)
- [1] M2: (structure of C18H14N4O2: HO-C6H4-N=N-C6H4-N=N-C6H4-OH)
- [1] HNO2 (and HCI) AND ≤10 °C OR NaNO2 AND HCI AND <10 °C
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