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CAIE A Level Chemistry 9701

Carboxylic acids and derivatives questions

Exam-style questions on Carboxylic acids and derivatives, ordered from foundation to challenge. Pick one, write your answer the way you would in the exam, and it comes back marked against the mark scheme, point by point.

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Written by Markquill to follow the Cambridge International syllabus. Markquill is independent and is not affiliated with or endorsed by Cambridge International.

  1. Suggest4 marksStandardA student hydrolyses methyl propanoate by heating it with dilute aqueous sodium hydroxide. Suggest what happens to the ester and name the two products of this reaction. In your answer, write a balanced equation for the…
  2. Explain4 marksStandardA student prepares ethyl ethanoate by heating ethanol with ethanoic acid in the presence of concentrated sulfuric acid. Two separate samples of the ester are then hydrolysed. Sample A is heated with dilute hydrochloric…
  3. Compare5 marksStandardA student plans to prepare propanoic acid. They consider two possible synthetic routes. Route 1: oxidation of propan-1-ol. Route 2: hydrolysis of propanenitrile. Compare these two routes for the preparation of…
  4. Explain4 marksStandardChloroethanoic acid, CH2ClCOOH, and trichloroethanoic acid, CCl3COOH, are both stronger acids than ethanoic acid, CH3COOH. Explain this trend in acidity.
  5. Explain4 marksStandardA student treats a sample of methanoic acid, HCOOH, with Tollens' reagent and warms the mixture. A silver mirror forms. Explain why methanoic acid reduces Tollens' reagent, and state the organic product of this reaction.
  6. Suggest4 marksStandardA student needs to convert propanoic acid, CH3CH2COOH, into propanoyl chloride, CH3CH2COCl, in the laboratory. Suggest a suitable reagent and the essential conditions for this conversion. In your answer, name the…
  7. Compare5 marksStandardMethanoic acid, HCOOH, and ethanedioic acid, HOOCCOOH, are both carboxylic acids that can be oxidised further. Compare the oxidation of methanoic acid with Fehling's reagent with the oxidation of ethanedioic acid with…
  8. Compare5 marksStandardA student hydrolyses samples of methyl propanoate separately under acidic and under alkaline conditions, heating both mixtures. Compare the products formed and the reagents used in the two hydrolysis reactions.
  9. Suggest4 marksStandardA student wishes to prepare benzoic acid, C6H5COOH, starting from benzonitrile, C6H5CN. Suggest two different sets of conditions for this conversion, and for each set state the reagent(s) and any further step needed to…
  10. Compare5 marksStandardEthyl ethanoate can be prepared by reacting ethanol with ethanoyl chloride, and phenyl benzoate can be prepared by reacting phenol with benzoyl chloride. Compare these two reactions, including the conditions required…
  11. Describe5 marksStandardPropanoic acid, CH3CH2COOH, reacts separately with aqueous sodium hydroxide and with aqueous sodium carbonate. Describe these two reactions, including the conditions and the products formed in each case.
  12. Suggest4 marksStandardBenzoyl chloride, C6H5COCl, reacts with phenol, C6H5OH, to form an ester. Suggest the structure of the ester formed, and state the conditions and the other product of this reaction.
  13. Suggest4 marksStandardA student wants to convert ethanoic acid into methyl ethanoate. The student plans to do this in two steps: first convert the acid into an acyl chloride, then react the acyl chloride with methanol. Suggest the reagent…
  14. Compare5 marksStandardPropyl propanoate can be made by reacting propan-1-ol with propanoic acid, and can be hydrolysed back to the alcohol and acid. Compare the reaction conditions used to make propyl propanoate from propan-1-ol and…
  15. Explain4 marksStandardPhenyl benzoate, C6H5COOC6H5, is an ester used in flavourings. It can be prepared by reacting benzoyl chloride, C6H5COCl, with phenol, C6H5OH. Explain why this method is preferred over reacting benzoic acid with…
  16. Compare5 marksStandardCompare the relative acidities of ethanol, phenol, ethanoic acid, and chloroethanoic acid. Explain the factors responsible for the differences in acidity.
  17. Compare5 marksStandardEthyl ethanoate and phenyl benzoate can both be produced by the reaction of an alcohol with an acyl chloride. Compare the reaction used to form ethyl ethanoate with that used to form phenyl benzoate. In your answer…
  18. Explain4 marksStandardPropanoic acid can be prepared from propan-1-ol and from propanenitrile. For each starting material, explain the reagents and conditions required to produce propanoic acid, and write an equation for the reaction.
  19. Describe5 marksStandardA student warms a sample of ethanedioic acid, HOOCCOOH, with an excess of warm acidified KMnO4 solution. The purple colour of the KMnO4 fades and a colourless gas is given off. Describe what is observed and identify…
  20. Compare5 marksStandardA student investigates the rates of hydrolysis of three compounds when added to water at room temperature. Compound A: ethanoyl chloride, CH3COCl Compound B: chloroethane, C2H5Cl Compound C: chlorobenzene, C6H5Cl The…
  21. Explain4 marksStandardAcyl chlorides undergo hydrolysis readily at room temperature, whereas alkyl chlorides and aryl chlorides are much less reactive. Explain this difference in reactivity by referring to the mechanisms involved.
  22. Explain4 marksStandardEthanoyl chloride reacts with ethanol to form ethyl ethanoate. Explain the reaction that occurs, including the equation for the reaction, the type of reaction, and the reason why acyl chlorides are more suitable than…
  23. Explain4 marksStandardA student adds a small piece of magnesium ribbon to a test-tube containing ethanoic acid. Effervescence is observed and the magnesium disappears. Explain, in terms of the reactions of carboxylic acids, what happens in…
  24. Compare5 marksStandardA student investigates two reactions of ethyl ethanoate. Compare the reaction between ethanol and ethanoic acid in the presence of concentrated sulfuric acid, with the reaction of ethyl ethanoate with hot dilute…
  25. Suggest5 marksChallengeA student wants to prepare the ester methyl ethanoate from methanol and ethanoic acid, and then hydrolyse a sample of the ester. Suggest the reagents and conditions for each step. (a) Preparation of methyl ethanoate…
  26. Suggest5 marksChallengeBenzonitrile, C6H5CN, can be hydrolysed to benzoic acid, C6H5COOH. Suggest a method for carrying out this conversion, including the reagents and conditions you would use, and how you would obtain the solid benzoic acid…
  27. Describe7 marksChallengeA student carries out the following experiments. Experiment A: A mixture of methylbenzene, hot alkaline KMnO4, and dilute acid is used to produce an organic product. Experiment B: Propanoic acid is heated with PCl5…
  28. Compare5 marksChallengeA student heats a sample of ethyl ethanoate with dilute hydrochloric acid. In a separate experiment, the student heats another sample of ethyl ethanoate with dilute aqueous sodium hydroxide. Compare the two reactions…
  29. Compare5 marksChallengeA student has a sample of butanoic acid. In one experiment, the acid is warmed with an excess of lithium tetrahydridoaluminate(III) (LiAlH4) in dry ether, followed by addition of water. In a second experiment, the acid…
  30. Describe7 marksChallengeA student investigates the reaction of ethanoyl chloride, CH3COCl, with water at room temperature. (a) Describe, in words, the addition–elimination mechanism for this reaction. (b) Explain why ethanoyl chloride…
  31. Describe7 marksChallengePropanoic acid, CH3CH2COOH, is a carboxylic acid. Describe two methods for the preparation of propanoic acid from other organic compounds. For each method, state the starting material, reagents, conditions, and the…
  32. Suggest7 marksChallengeA student prepares ethyl ethanoate by adding ethanol dropwise to ethanoyl chloride in a flask. The mixture fizzes and steamy fumes are given off. In a separate preparation, phenyl benzoate is made by adding phenol to…
  33. Describe7 marksChallengeA student has samples of propan-1-ol and propanal and wishes to prepare propanoic acid from each. Describe the reagents and conditions needed to oxidise propan-1-ol to propanoic acid, and outline how the product could…
  34. Explain6 marksChallengeA student prepares propanoic acid from propanenitrile, CH3CH2CN. Two methods are tried. Method 1: propanenitrile is refluxed with dilute sulfuric acid, then the mixture is neutralised and the product is isolated…
  35. Describe7 marksChallengeA flavouring compound found in strawberries is ethyl 2-methylbutanoate, CH3CH2CH(CH3)COOCH2CH3, the ester formed from ethanol and 2-methylbutanoic acid. A student plans to synthesize this ester in the laboratory and…
  36. Describe7 marksChallengeEthyl ethanoate can be produced by reacting ethanol with ethanoyl chloride. Describe how this reaction is carried out and describe the observations that would be made. State the type of reaction and the role of the…
  37. Describe7 marksChallengeMethylbenzene, C6H5CH3, can be converted into benzoic acid, C6H5COOH, by refluxing with an excess of hot alkaline KMnO4, followed by acidification with dilute sulfuric acid. Describe the conditions and the observations…
  38. Explain6 marksChallengeA student prepares the ester ethyl ethanoate by reacting ethanol with ethanoic acid in the presence of concentrated sulfuric acid. A second sample of ethyl ethanoate is divided into two portions. One portion is heated…
  39. Explain6 marksChallengeThe pH of a 0.1 mol dm^-3 aqueous solution of chloroethanoic acid, ClCH2COOH, is lower than the pH of a 0.1 mol dm^-3 aqueous solution of ethanoic acid, CH3COOH. Explain this observation in terms of the inductive…
  40. Describe7 marksChallengeA student plans to prepare two esters: ethyl ethanoate and phenyl benzoate, each from an acyl chloride and an alcohol or phenol. Describe the reactions, including the reagents and conditions required, and explain why…
  41. Describe7 marksChallengeA student prepares the ester ethyl ethanoate by heating a mixture of ethanol and ethanoic acid with concentrated sulfuric acid. (a) Name the type of reaction and state the role of the concentrated sulfuric acid. (b)…
  42. Compare5 marksChallengeChloroethanoic acid, dichloroethanoic acid and trichloroethanoic acid are all stronger acids than ethanoic acid. Compare the acidities of these four acids, and explain the trend in terms of the inductive effect of the…
  43. Explain6 marksChallengeA student plans to prepare two esters in the laboratory. Ester 1: ethyl ethanoate, from ethanol and ethanoyl chloride Ester 2: phenyl benzoate, from phenol and benzoyl chloride Explain, with reference to these two…