A LevelChemistryOCRExam Questions6. Organic Chemistry & AnalysisOrganic Synthesis

Organic Synthesis (OCR A Level Chemistry A): Exam Questions

Exam code: H432

3 hours31 questions

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Organic Synthesis

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11 mark

CN– ions react with haloalkanes and with carbonyl compounds.

Which row gives the correct mechanisms for the reactions?

 

Reaction of CN- with haloalkanes

Reaction of CN- with carbonyl compounds 

A

Electrophilic substitution 

Electrophilic addition

B

Electrophilic substitution 

Nucleophilic addition

C

Nucleophilic substitution 

Electrophilic addition

D

Nucleophilic substitution 

Nucleophilic addition

    Choose your answer

    21 mark

    Phenylamine can be produced in a two-stage synthesis shown below.

    imT7nJgb_6-8-q2-phenylamine

    What is the correct classification of the steps?

     

    Step 1

    Step 2

    A

    Electrophilic substitution

    Reduction

    B

    Nucleophilic addition

    Reduction

    C

    Nitration

    Oxidation

    D

    Nucleophilic addition

    Oxidation

      Choose your answer

      31 mark

      Propanal can be converted to propanoyl chloride via a two-stage synthesis route shown below.

      propanal  rightwards arrow with Step space 1 on top  propanoic acid  rightwards arrow with Step space 2 on top  propanoyl chloride

      What are the correct reagents for steps 1 and 2?

       

      Step 1

      Step 2

      A

      H2O / HCl

      SOCl2

      B

      NaBH4 / H2O

      H2O / HCl

      C

      K2Cr2O7 / H+

      SOCl2

      D

      K2Cr2O7 / H+

      H2O

        Choose your answer

        41 mark

        Many organic products can be synthesised from a few starting compounds using the correct reagents and conditions.

        Which skeletal formula is a correct example for the functional groups stated?

         

        Functional groups

        Example

        A

        Alcohol and nitrile

        6-8-q4-a

        B

        Alcohol and nitrile

        6-8-q4-b

        C

        Ester and alkene

        6-8-q4-c

        D

        Carbonyl and haloalkane

        6-8-q4-d

          Choose your answer

          51 mark

          Which of the following compounds can not be formed directly from an alcohol?

          • Amine

          • Ester

          • Alkene

          • Ketone

          Choose your answer

          11 mark

          The structure of the amino acid phenylalanine is shown below.

          phenylalanine

          Which functional group(s) is / are in a molecule of phenylalanine?

          1. Amine

          2. Amide

          3. Alcohol

          • 1, 2 and 3

          • Only 1 and 2

          • Only 2 and 3

          • Only 1

          Choose your answer

          21 mark

          Which statement about melting point tests is not correct?

          • Impurities can raise or lower the melting point of organic solids

          • The melting point tubes must be heated slowly

          • Organic solids with high melting points can decompose before melting

          • The organic solid must be finely powdered and dry

          Choose your answer

          31 mark

          The synthesis of ethyl butanoate can be carried out using the reaction scheme shown below.

                                  C4H9Br   rightwards arrow with Step space 1 on top  C4H9OH  rightwards arrow with Step space 2 on top  C3H7COOH  rightwards arrow with Step space 3 on top  C3H7COOC2H5  

          What is the correct classification of the steps?

           

          Step 1

          Step 2

          Step 3

          A

          Substitution

          Oxidation

          Condensation

          B

          Addition

          Substitution

          Condensation

          C

          Oxidation

          Substitution

          Condensation

          D

          Substitution

          Oxidation

          Substitution

            Choose your answer

            41 mark

            Propanone can be converted to 2-bromopropane using the three step synthetic scheme shown below. 

            Propanone rightwards arrow with Step space 1 on top propan-2-ol rightwards arrow with Step space 2 on toppropene rightwards arrow with Step space 3 on top2-bromopropane

            What are the correct reagents for each step?

             

            Step 1

            Step 2

            Step 3

            A

            K2Cr2O7 / H2SO4

            Conc. NaOH

            HBr

            B

            NaBH4

            Al2O3

            HBr

            C

            H2O / H2SO4

            Al2O3

            Br2

            D

            NaBH4

            K2Cr2O7 / H2SO4

            HBr

              Choose your answer

              51 mark

              Butylamine can be prepared in two steps from 1-bromopropane

              CH3CH2CH2Br → X → CH3CH2CH2CH2NH2

              What is the structural formula of X?

              • CH3CH2CH2OH

              • CH3CH=CH2

              • CH3CH2CH2CN

              • CH3CH2CH2CHO

              Choose your answer

              11 mark

              Which row contains the correct number of minimum steps to convert an aldehyde into the given compound?

               

              Amide

              Primary amine

              Dihalogenoalkane

              A

              2 steps

              3 steps

              4 steps

              B

              4 steps

              2 steps

              3 steps

              C

              3 steps

              4 steps

              2 steps

              D

              2 steps

              3 steps

              3 steps

                Choose your answer

                21 mark

                Propyl 4-aminobenzoate or risocaine is a local anesthetic that can be synthesised from 4-nitrobenzaldehyde via the following three step synthesis.

                nwnKtwWD_7-8-h-q1-mcq-aqa-al-chemistry

                Which row contains the correct molecular formulae of compounds X and Y?

                 

                Compound X

                Compound Y

                A

                C7H6NO3

                C9H11NO4

                B

                C7H6NO4

                C10H11NO3

                C

                C7H5NO4

                C10H11NO4

                D

                C7H5NO3

                C9H11NO3

                  Choose your answer

                  31 mark

                  Which statement about the purification of an organic solid is not correct?

                  • Recrystallisation uses a solvent in which the organic solid dissolves when hot but will crystallise out when cold. 

                  • Hot filtration can be used after recrystallisation to remove any solid impurities that remain. 

                  • Impurities tend to lower the melting point of organic solids such as aspirin. 

                  • A water bath can be used to determine the melting point of the organic solid. 

                  Choose your answer

                  41 mark

                  Below is a sequence of reactions from the starting molecule bromopropane.

                  l4hQIC9o_ocr-a2-6-8h-mcq-q2-reaction-sequence

                  Which reagent or type of mechanism is not correct for the indicated step?

                  • Step 1 NaCN / Nucleophilic substitution

                  • Step 2 H2O/HCl / Hydrolysis

                  • Step 3 SOCl2 / Chlorination 

                  • Step 4 methylamine / Nucleophilic substitution 

                  Choose your answer

                  51 mark

                  A reaction sequence starting from ethene is shown below.

                  ocr-a2-6-8h-mcq-q3-reaction-sequence

                  Which statement(s) is/are correct?

                  1. Two of the molecules belong to the same homologous series.

                  2. Reaction 4 produces a compound that will conduct electricity in the molten state.

                  3. Reactions 1, 2, 3 and 5 require sulfuric acid. 

                  • 1, 2 and 3

                  • Only 1 and 2

                  • Only 2 and 3

                  • Only 1

                  Choose your answer