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Organic Analysis (AQA AS Chemistry): Exam Questions

Exam code: 7404

3 hours45 questions

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Organic Analysis

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11 mark

Which organic functional group could have produced the infrared spectrum below?

q1-3-6-easy-mcq-organic-analysis

  • An aldehyde

  • An alcohol

  • A carboxylic acid

  • A ketone

Choose your answer

21 mark

Which of the following cannot be obtained from an infrared spectrum?

  • The molecular mass

  • The presence of C=O bonds

  • The presence of O-H bonds

  • The identity of a compound through comparison with other spectra

Choose your answer

31 mark

What chemical reagent(s) could be used to determine that bromide ions were present in a solution?

  • Silver nitrate (aq) 

  • Barium chloride (aq)

  • Silver nitrate (aq) + dilute ammonia (aq)

  • Silver nitrate (aq) + concentrated ammonia (aq)

Choose your answer

41 mark

2-methylpropan-1-ol is distilled in the presence of acidified potassium dichromate(VI). The distillate is then warmed with Fehling’s solution and a brick red precipitate forms.

Which functional group is present in the distillate?

  • Ketone

  • Aldehyde

  • Carboxylic acid

  • Tertiary alcohol

Choose your answer

51 mark

What is meant by the term ‘fingerprint region’ on an infrared spectrum?

 

Between 500 - 1500 cm-1

Absorption for C-O bond

Measures intensity of absorption

Used for comparison against known compounds

A

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B

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C

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D

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    Choose your answer

    61 mark

    In mass spectrometry, what is the molecular ion peak (M+) of ethanoic acid?

    • [CH3COOH]+, m/z = 60

    • [CH3COOH], m/z = 60

    • [CH3COOH]+, m/z = 59

    • [CH3COOH], m/z = 61

    Choose your answer

    71 mark

    What organic functional group could have produced this infrared spectrum?

    q7-3-6-easy-mcq-organic-analysis

    • Alcohol

    • Carboxylic acid

    • Aldehyde

    • Carbonyl

    Choose your answer

    81 mark

    What would be observed if aqueous magnesium sulfate was reacted with acidified barium chloride?

    • Cream precipitate

    • Yellow precipitate + effervescence

    • White precipitate

    • Colour change orange to green

    Choose your answer

    91 mark

    Using the mass spectrum below, what is the molecular ion peak of 2-methylbutane?

    q9-3-6-easy-mcq-organic-analysis

    • 27

    • 43

    • 57

    • 72

    Choose your answer

    101 mark

    Unknown reagent Z is analysed and the results of qualitative tests are below.

     

    Test

    Observation

    1.

    Adding bromine water

    No change

    2.

    Testing with indicator paper

    pH = 7

    3.

    Adding sodium hydrogen carbonate solution

    No change

    4.

    Adding acidified potassium dichromate(VI) solution and warming

    Colour change from orange to green

    5.

    Adding Tollens’ solution to the products of test 4 and warming

    Silver mirror produced

     What is the possible identity of the reagent Z?

    • Cyclohexene

    • Butan-1-ol

    • 2-chloropentanal

    • 3-hexanone

    Choose your answer

    11 mark

    Which of the following compounds would form an orange-red precipitate when heated with Fehling’s solution?

    • CH3CHO

    • CH3CH2CH2CH2COOH

    • CH3CH2CH2Cl

    • CH3CH2COCH3

    Choose your answer

    21 mark

    Which alcohol is not likely to have a fragment ion at m/z at 43 in its mass spectrum?

    • CH3CH2CH2CH2OH

    • CH3CH(OH)CH2CH2CH3

    • (CH3)2CHCH2OH

    • CH3CH2CH(OH)CH3

    Choose your answer

    31 mark

    Butanal, CH3CH2CH2CHO, and butanone, CH3CH2COCH3, are carbonyl compounds.

    When these compounds are compared using analytical methods, which of the following statements is not correct?

    • The compounds produce different patterns in the fingerprint region of the IR spectrum

    • The carbonyl groups absorb at frequencies in the same region of the IR spectrum

    • The compounds have molecular ion peaks at different mass to charge ratios in a mass spectrum

    • The compounds produce different fragmentation patterns in a mass spectrum

    Choose your answer

    41 mark

    Bromine exists as two isotopes 79Br and 81Br, which are found in almost equal abundance.

    Which of the following statements is correct?

    • 79Br is more reactive than 81Br

    • The mass spectrum of C3H7Br has two molecular ion peaks at 122 and 124

    • The atomic radius of 79Br is less than the atomic radius of 81Br

    • The first ionisation energy of 79Br is less than the first ionisation energy of 81Br

    Choose your answer

    51 mark

    Which compound is shown in the infrared spectrum below?

    q5-3-6-medium-mcq-organic-analysis

    • Butanoic acid

    • Butanal

    • But-1-ene

    • Butan-1-ol

    Choose your answer

    61 mark

    Which pair of compounds would you expect to both have a singly charged peak at m/z = 29 in the mass spectrum?

    • propanal and propanone

    • propan-1-ol and propanal

    • propan-2-ol and propanal

    • propanone and propan-2-ol

    Choose your answer

    71 mark

    Which compound below does not contain the functional group shown by the infrared spectrum?

    q7-3-6-medium-mcq-organic-analysis

    • carboxylic acid

    • alcohol

    • ketone

    • aldehyde

    Choose your answer

    81 mark

    Which of the ketones listed would not be expected to have a peak in its mass spectrum at m/z = 57?

    • CH3CH2CH2COCH2CH3

    • CH3CH2COCH2CH3

    • (CH3)2CHCOCH3

    • CH3CH2COCH3

    Choose your answer

    91 mark

    Crotonaldehyde, CH3CH=CHCHO, occurs in soybean oils and can be formed from its alcohol.

    Other than the alcohol of crotonaldehyde, what reagents and experimental conditions are needed for producing crotonaldehyde?

     

    Reflux

    Distillation

    K2Cr2O7

    K2Cr2O7/H+

    A

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    B

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    C

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    D

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      Choose your answer

      101 mark

      Calcium iodide is reacted with silver nitrate and a yellow coloured precipitate is produced.

      Which pair of responses helps to confirm the identity of the anion?

       

      Solubility in dilute ammonia

      Solubility in concentrated ammonia

      A

      insoluble

      insoluble

      B

      insoluble

      soluble

      C

      soluble

      insoluble

      D

      soluble

      soluble

        Choose your answer

        11 mark

        Mixture F is produced upon refluxing compound G with aqueous sodium hydroxide.

        Upon distillation of F with acidified potassium dichromate(VI), propanone is produced. Mixing G with aqueous silver nitrate and dilute nitric acid gives a cream precipitate.

        What is the identity of compound G?

        • CH3CHICH3

        • CH3CHBrCH3

        • CH3CH2CH2I

        • CH3CH2CH2Br 

        Choose your answer

        21 mark

        When the apparatus below was used with compound E, a brick-red precipitate formed in the right-hand tube.

        q2-3-6-hard-mcq-organic-analysis

        Which compound could be E?

         

        CH3OH

        CH3CH2CH2OH

        CH3CH(OH)CH3

        HCOOCH2CH2CH3

        A

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        B

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        C

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        D

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          Choose your answer

          31 mark

          An alcohol can be prepared by hydrolysing the halogenoalkane C4H7CHClCH3 with aqueous sodium hydroxide.

          The infrared spectrum for C4H7CHClCH3 is shown in with the C–Cl bond absorption is labelled.

          q3-3-6-hard-mcq-organic-analysis

          How will the infra-red spectroscopy change as a result of the above reaction?

           

          Appearance of peak at 3230 - 3550 cm−1

          Appearance of peak at 2500 - 3000 cm−1

          Disappearance of peak at 500 - 800 cm−1

          Appearance of peak at 1680 - 1750 cm−1

          A

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          B

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          C

          ✓

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          D

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          ✓

            Choose your answer

            41 mark

            The mass spectra of three compounds A, B and C are shown below.

            q4-1-3-6-hard-mcq-organic-analysis
            q4-2-3-6-hard-mcq-organic-analysis

            Which of the following features of the three compounds A, B and C shows the molecular formula is C4H10O?

            • All show a molecular ion peak at 74

            • All show a molecular ion peak at 15

            • All show a molecular ion peak at 73

            • All show a molecular ion peak at 44

            Choose your answer

            51 mark

            The infrared spectrum of an unknown compound is shown below.

            q5-1-3-6-hard-mcq-organic-analysis

            Which compound could have produced the infrared spectrum?

            q5-2-3-6-hard-mcq-organic-analysis

              Choose your answer

              61 mark

              A compound XFn is a fluoride of another halogen, X, and it is known that n > 1. The highest mass peak in the spectrum of XFn is the parent ion and has a single peak at m/z = 222.

              Which of the following statements is incorrect?

              • n = 5

              • X electronegativity value＜ F

              • The compound could contain bromine

              • The compound is a fluoride of iodine

              Choose your answer

              71 mark

              A sample is analysed by mass spectrometry and infrared spectroscopy. The following incomplete data is obtained.

              Mass Spectrometry

              Infrared Spectroscopy

              Molecular ion peak at m/z = 128

              Sharp peak at 1720 cm-1

              Fragment ion peak at m/z = 15

              No broad peak around 3200 cm-1

              Which of the following compounds could be present in the sample?

              q7-3-6-hard-mcq-organic-analysis

                Choose your answer

                81 mark

                Which of the following isomeric alcohols, with molecular formula C5H12O, cannot be oxidised by acidified potassium dichromate?

                q8-3-6-hard-mcq-organic-analysis

                  Choose your answer

                  91 mark

                  In mass spectrometry, which compound forms a molecular ion with a different precise molecular mass from the other three compounds?

                  • Cyclopentanol

                  • Dimethylbutane

                  • Pentanone

                  • Methylbutanal

                  Choose your answer

                  101 mark

                  This question is about the reaction between cyclopropanone and an excess of methanol which forms a hemiketal compound as shown below.

                  q10-3-6-hard-mcq-organic-analysis

                  Which infra-red absorption would the products not produce?

                  • 1700 cm-1

                  • 2900 cm-1

                  • 1200 cm-1

                  • 3300 cm-1

                  Choose your answer