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DP IB Chemistry: HL

Topic Questions

Home / IB / Chemistry: HL / DP / Topic Questions / 20. Organic Chemistry (HL only) / 20.1 Types of Organic Reactions / Structured Questions: Paper 2


20.1 Types of Organic Reactions

Question 1a

Marks: 2
a)
Halogen molecules can react with alkenes to produce halogenoalkanes which contain two halogen atoms. Explain why halogen molecules can react with alkenes.
[2]
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    Question 1b

    Marks: 3
    b)
    Outline the mechanism for the reaction between 1-methylcyclohex-1-ene and hydrogen bromide, HBr, to form the major product. 
    [3]
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      Question 1c

      Marks: 3
      c)
      Explain why a major product and minor product are produced in the reaction outlined in part b).
      [3]
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        Question 1d

        Marks: 5
        d)
        The major product from the reaction of part b) forms an alcohol when reacted with water. Predict the type of mechanism for this reaction and the structure of the alcohol. 

        i)
        State the type of mechanism that will occur. 
        [1]
        ii)
        Give the structure of the alcohol formed.
        [1]
        iii)
        Explain why ethanol would be a suitable solvent for this reaction
        [2]

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          Question 2a

          Marks: 2
          a)
          C5H11Cl is a chiral molecule.

          Draw the three-dimensional shape of each enantiomer of this isomer showing their spatial relationship to each other.
          [2]
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            Key Concepts
            Optical Isomers

            Question 2b

            Marks: 3
            b)
            One of these enantiomers undergoes alkaline hydrolysis and approximately 75 % of the product formed shows an inversion of configuration.

            Outline the mechanism that causes approximately 100% of the inversion of configuration. 
            [3]
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              Key Concepts
              SN2 Mechanism

              Question 2c

              Marks: 2
              c)
              Explain why the inversion of configuration is 75%.
              [2]
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                Question 2d

                Marks: 1
                d)
                Explain what would happen to the rate of the mechanism in part b) if the concentration of alkali is doubled.
                 
                [1]
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                  Key Concepts
                  SN2 Mechanism

                  Question 2e

                  Marks: 2
                  e)
                  Comment on the rate if ammonia was reacted with C5H11Cl compared to alkaline hydrolysis. 
                  [2]
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                    Question 3a

                    Marks: 3
                    a)
                    The theoretical molecule cyclohexa-1,3,5-triene reacts differently with bromine than benzene. 

                    Benzene will react with bromine in the presence of aluminium bromide. Outline the mechanism for this reaction.
                    [3]



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                      Question 3b

                      Marks: 1
                      b)

                      State the name of the mechanism that occurs during the reaction between cyclohexa-1,3,5-triene and bromine. 

                      [1]

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                        Question 3c

                        Marks: 3
                        c)
                        The nitration of benzene is the first important step in the manufacture of dyes and explosives.

                        i)
                        Outline the generation of the electrophile for the nitration of benzene by writing an equation. 
                        [1]

                        ii)
                        Indicate in your equation which reactant is acting as a Brønsted Lowry base. 
                        [1]

                        iii)
                        Explain your answer and identify the conjugate acid and base pairs in the reaction.
                        [1]



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                          Question 3d

                          Marks: 3
                          d)
                          Phenylamine can be formed from nitrobenzene in two steps. The first step involves heating nitrobenzene in a water bath under reflux with a mixture of zinc and hydrochloric acid.

                          i)
                          Write a full redox equation for this first step. 
                          [1]
                          ii)
                          Explain how phenylamine is formed in the second step of this reaction. 
                          [2]
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                            Question 3e

                            Marks: 3
                            e)
                            Explain why benzene can only undergo substitution reactions. 
                            [3]
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                              Question 4a

                              Marks: 2
                              a)
                              Aqueous sodium tetrahydridoborate, NaBH4, is a common reducing agent.

                              State the IUPAC name of the two isomers with the formula C3H6O that can be reduced by aqueous NaBH4.
                              [2]
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                                Key Concepts
                                Reduction Reactions

                                Question 4b

                                Marks: 2
                                b)
                                State the IUPAC name of two non-cyclic isomers with the formula C3H6O that cannot be reduced by aqueous NaBH4.
                                [2]
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                                  Key Concepts
                                  Reduction Reactions

                                  Question 4c

                                  Marks: 4
                                  c)

                                  When NaBH4 is used as a reducing agent followed by the addition of acid, the reduction products of ketones can exhibit optical isomerism, while the reduction products of aldehydes cannot.

                                  i)
                                  Classify the reduction products of aldehydes and ketones.
                                  [2]

                                  ii)
                                  Explain why the reduction products of ketones can exhibit optical isomerism, while the reduction products of aldehydes cannot.
                                  [2]
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                                    Key Concepts
                                    Reduction Reactions

                                    Question 4d

                                    Marks: 1
                                    d)
                                    Deduce the structure when the following compound is reduced using NaBH4.
                                    ib-hl-chem-20-1-sq-h-q4d
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                                      Key Concepts
                                      Reduction Reactions