Proton (1H) NMR spectroscopy: past paper questions

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• Question 8May/June 2026, paper 41Structured10 marksHas a diagram

  Secondary amine M can be made by the three-step synthesis shown in Figure 8.1. Write an equation for the reaction of ${\text{CH}}_3\text{COOH}$ with ${\text{SOCl}}_2$ in step 1.

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• Question 6Oct/Nov 2025, paper 41Structured7 marksHas a diagram

  Thin-layer and gas/liquid chromatography can be used to separate mixtures into their individual components. Define the following terms used in chromatography.

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• Question 6Oct/Nov 2024, paper 41Structured14 marksHas a diagram

  Benzene, ${\mathrm{C}}_6{\mathrm{H}}_6$, reacts with chloroethane, ${\mathrm{C}}_2{\mathrm{H}}_5\mathrm{C}\mathrm{l}$, in the presence of a suitable catalyst to form ethylbenzene, ${\mathrm{C}}_6{\mathrm{H}}_5{\mathrm{C}}_2{\mathrm{H}}_5$.

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• Question 8Oct/Nov 2023, paper 41Structured14 marksHas a diagram

  Capsaicin is found in chilli peppers. You should assume the $\mathrm{C}{\mathrm{H}}_3\mathrm{O}$ group is unreactive in the reactions involved in this question. Name all the functional groups in capsaicin in addition to the $\mathrm{C}{\mathrm{H}}_3\mathrm{O}$ group.

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• Question 8May/June 2026, paper 42Structured8 marksHas a diagram

  Give the full name of the substance used in NMR spectroscopy as the standard for chemical shift measurements.

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• Question 8Oct/Nov 2024, paper 42Structured12 marksHas a diagram

  The amino acid serine, ${\text{HOCH}}_2\text{CH}({\text{NH}}_2)\text{COOH}$, exists in two optically active forms. These optical isomers, isomer P and isomer Q, are shown in Fig. 8.1.

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• Question 8Oct/Nov 2023, paper 42Structured12 marksHas a diagram

  Lactic acid, $\mathrm{C}{\mathrm{H}}_3\mathrm{C}\mathrm{H}(\mathrm{O}\mathrm{H})\mathrm{C}\mathrm{O}\mathrm{O}\mathrm{H}$, is the only monomer needed to form the polymer polylactic acid, PLA. Draw a short length of the PLA polymer chain, including a minimum of two monomer residues.

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• Question 7May/June 2025, paper 41Structured11 marksHas a diagram

  A hydrocarbon is known to be either compound D or compound E. Give the systematic name of E.

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• Question 6May/June 2024, paper 41Structured15 marksHas a diagram

  State what is meant by partition coefficient, $K_{\mathrm{p}\mathrm{c}}$.

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• Question 7May/June 2023, paper 41Structured18 marksHas a diagram

  State the relative basicities of ethanamide, diethylamine and ethylamine in aqueous solution.

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• Question 8May/June 2025, paper 42Structured6 marksHas a diagram

  Compound A is analysed by carbon-13 NMR and proton (${}^1\mathrm{H}$) NMR spectroscopy. State the reference substance and a solvent that can be used in NMR spectroscopy.

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• Question 8May/June 2023, paper 42Structured15 marksHas a diagram

  Describe the difference in reactivity between chloroethane and chlorobenzene with ${\text{OH}}^{-}\text{(aq)}$.

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• Question 9May/June 2024, paper 42Structured12 marksHas a diagram

  Explain why trichloroethanoic acid, ${\text{CCl}}_3\text{COOH}$, is more acidic than ethanoic acid, ${\text{CH}}_3\text{COOH}$.

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• Question 6May/June 2024, paper 43Structured15 marksHas a diagram

  State what is meant by partition coefficient, $K_{\mathrm{p}\mathrm{c}}$.

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