ASChemistryCambridge (CIE)Exam Questions18. Carboxylic Acids & DerivativesCarboxylic Acids

Carboxylic Acids (Cambridge (CIE) AS Chemistry): Exam Questions

Exam code: 9701

1 hour20 questions

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Carboxylic Acids

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1
1 mark

'Trans fats' can be found in some vegetable oils and are known to lead to increased blood cholesterol levels.

In the diagrams below, R1 and R2 are different hydrocarbon chains.

Which structure represents an optically active trans fatty acid?

  • Trans fatty acid structure without a chiral carbon, showing R1 and R2 groups on opposite sides of the C=C double bond
  • Cis fatty acid structure showing R1 and R2 groups on the same side of the C=C double bond
  • Trans fatty acid structure with a chiral carbon, showing R1 and R2 groups on opposite sides of the C=C double bond with a chiral centre
  • Cis fatty acid structure showing R1 and R2 groups on the same side of the C=C double bond

Choose your answer

2
1 mark

Which reaction does not produce propanoic acid?

  • Heating propan-1-ol under reflux with acidified potassium dichromate(VI).

  • Heating propanal under reflux with acidified potassium dichromate(VI).

  • Heating propanenitrile under reflux with aqueous sodium hydroxide.

  • Heating propanenitrile under reflux with dilute sulfuric acid.

Choose your answer

3
1 mark

Propanenitrile, CH3CH2C≡N, is used to produce propanoic acid.

What are the conditions for this reaction?

  • H+ / H2O, heat under reflux

  • H+ / Na2Cr2O7

  • NaBH4

  • NaOH, heat under reflux

Choose your answer

1
1 mark

Sour milk contains a compound called lactic acid (2-hydroxypropanoic acid) which has the molecular formula CH3CH(OH)CO2H.

Which of the following reactions could lactic acid undergo?

  • CH3CH(OH)CO2H + Cl2 → CH3CH(Cl)CO2H + HOCl

  • CH3CH(OH)CO2H + HCO2H → CH3CH(O2CH)CO2H + H2O

  • CH3CH(OH)CO2H + CH3OH → CH3CH(OCH3)CO2H + H2O

  • CH3CH(OH)CO2H + NaHCO3 → CH3CH(ONa)CO2H + H2O + CO2

Choose your answer

2
1 mark

Apples contain a compound called malic acid.

Structural formula of malic acid (2-hydroxybutanedioic acid), showing two carboxylic acid groups and one secondary alcohol group

Which substance will react with only one hydroxyl group in malic acid under suitable conditions?

  • Cr2O72- / H+ (aq)

  • Na (s)

  • NaOH (aq)

  • PCl5

Choose your answer

3
1 mark

The natural bacterial fermentation of milk produces a compound called propanoic acid.

Propanoic acid is partly responsible for the flavour of Swiss cheese. Its structure is shown below:

Structural formula of propanoic acid (CH3CH2COOH), showing the ethyl group attached to the carboxylic acid group

Which starting materials could be used to produce propanoic acid?

CH3CH2CN

CH3CH2CHO

CH3CH2CH2OH

A

✓

✓

✓

B

✓

✓

x

C

x

✓

✓

D

✓

x

x

    Choose your answer

    1
    1 mark

    Sirolimus is a drug used to treat patients after kidney transplants.

    Structural formula of sirolimus, a macrolide drug containing both ester and amide bonds

    Sirolimus produces an equimolar mixture of two organic products, on reaction with hot aqueous sodium hydroxide.

    What is the structural formula of the product with the lower relative molecular mass?

    • Structural formula of option A, an organic product from sirolimus hydrolysis
    • Structural formula of option B, an organic product from sirolimus hydrolysis
    • Structural formula of option C, the organic product with the lower relative molecular mass from sirolimus hydrolysis
    • Structural formula of option D, an organic product from sirolimus hydrolysis

    Choose your answer

    2
    1 mark

    Compound K, C5H12O, is oxidised by acidified aqueous potassium dichromate(VI) to compound L.

    Compound L reacts with butan-2-ol in the presence of a little concentrated sulfuric acid to give liquid M.

    What could be the formula of liquid M?

    • (CH3)2CHCH2CO2C(CH3)3

    • CH3(CH2)3CO2(CH2)3CH3

    • CH3(CH2)3CO2CH(CH3)CH2CH3

    • CH3(CH2)2CO2CH2CH2(CH3)2

    Choose your answer

    3
    1 mark

    Compound X can be made from 2-hydroxybutanoic acid.

    Structural formula of compound X, a cyclic diester formed from two molecules of 2-hydroxybutanoic acid condensing together

    What should be heated with 2-hydroxybutanoic acid in order to make compound X?

    • Acidified aqueous potassium manganate(VII)

    • Aluminium oxide

    • Concentrated sulfuric acid

    • Dilute sodium hydroxide

    Choose your answer

    4
    1 mark

    Oxaloacetic acid can be synthesised from fumaric acid in a two-step process involving intermediate Z.

    HO2CCH=CHCO2H →step 1 Z →step 2 HO2CCOCH2CO2H

    Each step involved can be achieved in the laboratory by using a single reagent.

    Which row identifies intermediate Z and the reagent for step 2?

    Z

    Reagent for step 2

    A

    HO2CCH(OH)CH2CO2H

    Fehling's solution

    B

    HO2CCH(OH)CH2CO2H

    Acidified aqueous potassium manganate(VII), heat

    C

    HO2CCHBrCH2CO2H

    Acidified aqueous potassium manganate(VII), heat

    D

    HO2CCHBrCH(OH)CO2H

    Warm NaOH (aq)

      Choose your answer

      5
      1 mark

      Citric acid has the formula HO2CCH2C(OH)(CO2H)CH2CO2H.

      What is the volume of 0.2 mol dm–3 aqueous sodium hydroxide required to neutralise a solution containing 0.008 mol of citric acid?

      • 40 cm3

      • 80 cm3

      • 120 cm3

      • 160 cm3

      Choose your answer

      6
      1 mark

      The compound 2-ethyl-3-methylbutanoic acid has the following structure:

      Structural formula of 2-ethyl-3-methylbutanoic acid, showing a branched 4-carbon chain with an ethyl group at C2 and methyl group at C3

      Which compound will produce 2-ethyl-3-methylbutanoic acid by heating under reflux with ethanolic sodium cyanide and subsequent acid hydrolysis of the reaction product?

      • Structural formula of option A, the correct halogenoalkane precursor that gives 2-ethyl-3-methylbutanoic acid after NaCN substitution and acid hydrolysis
      • Structural formula of option B, a halogenoalkane that would give a different carboxylic acid product
      • Structural formula of option C, a halogenoalkane that would give a different carboxylic acid product
      • Structural formula of option D, a halogenoalkane that would give a different carboxylic acid product

      Choose your answer

      7
      1 mark

      Which compound requires the largest amount of cold aqueous sodium hydroxide for the complete neutralisation of 1 mole?

      • Aspirin, HOOC-C6H4-OCOCH3

      • Gluconic acid, HOCH2-(CH(OH))4COOH

      • Lactic acid, CH3-CH(OH)-COOH

      • Malic acid, HOOC-CH(OH)-CH2COOH

      Choose your answer