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IBChemistry: HLDPExam Questions20. Organic Chemistry (HL only)20.2 Synthetic Routes

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First teaching 2014

Last exams 2024

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Synthetic Routes (DP IB Chemistry: HL)

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20.2 Synthetic Routes

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20.2 Synthetic Routes

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1
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Propanone is made by a two stage process. 

The second stage involves oxidation. 

Propene    →     X   →   Propanone

What is the functional group of compound X?

  • COOH

  • OH

  • COO

  • C=O

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2
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4-nitrophenol can be produced from phenol.

20-2-fromiing-4-nitrophenol

What is the name of the mechanism used to make 4-nitrophenol? 

  • Nucleophilic substitution

  • Nucleophilic addition

  • Electrophilic addition

  • Electrophilic substitution

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3
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4-methylpentanal can be formed by the oxidation of 4-methylpentan-1-ol.

Which reagent is used as an oxidising agent for this conversion?

  • NaBH4

  • NaOH

  • K2Cr2O7

  • LiAlH4

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41 mark

Which reaction(s) can alkenes undergo? 

  1. Addition
  2. Hydration
  3. Reduction

  • I and II only

  • I and III only

  • II and III only

  • I, II and III

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5
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Phenylamine can be formed from nitrobenzene. 

formation-of-phenylamine

What are the reagents used and the name of this reaction?

  Reagents  Reaction 
A. Sn and conc H2SO4 Substitution
B. NaOH Addition
C. Conc HNO3 and conc HCl Reduction
D. Sn and conc HCl Reduction

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    11 mark

    The synthesis of ethyl butanoate can be carried out in three steps:

                                             I                   II                      III

                            C4H9Br   →  C4H9OH  →  C3H7COOH  →  C3H7COOC2H5  

    What is the correct classification of the steps?

     

    I

    II

    III

    A

    substitution

    oxidation

    condensation

    B

    addition

    substitution

    condensation

    C

    oxidation

    substitution

    condensation

    D

    substitution

    oxidation

    substitution

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      21 mark

      The synthesis of 2-propyl propanoate can be carried out in two steps:

                                                     I                                

                               CH3COCH3   →  CH3CH(OH)CH3

                                                     II   

                        CH3CH(OH)CH3  → C2H5COOCH(CH3)2 

      What are the reagents needed in I and II?

       

      I

      II

      A

      potassium dichromate(VI)

      sulfuric acid, propanoic acid

      B

      sodium borohydride

      sulfuric acid, propanoic acid

      C

      sodium borohydride

      sulfuric acid, ethanoic acid

      D

      potassium dichromate(VI)

      sulfuric acid, ethanoic acid

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        31 mark

        The synthesis of phenylamine can be carried out in two steps:

                                           I                    II             

                              C6H6   →  C6H5NO2   → C6H5NH2                                  

        What are the reaction types in I and II?

         

        I

        II

        A

        oxidation

        substitution

        B

        addition

        substitution

        C

        substitution

        reduction

        D

        oxidation

        reduction

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          41 mark

          Which of the following reactions produces only pentan-2-ol?

          • Water and pent-1-ene

          • 1-bromopentane and ethanolic NaOH

          • Water and pent-2-ene

          • 2-bromopentane and ethanolic NaOH

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          51 mark

          Which compound could be X in this two step reaction pathway?

          C3H8 → X  → C3H7OH

          • C2H5CN

          • C3H7Cl

          • C3H6Cl2

          • C2H5COOH

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          1
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          The equation below shows the conversion of propanal to propyl ethanoate.

          formation-of-ester-from-aldehyde   What are the reagents used and the reactions taking place?

            Reaction 1  Reagents 1 Reaction 2 
          A

          oxidation

          K2Cr2O7 and H2SO4

          nucleophilic substitution (condensation) 
          B

          reduction

           NaBH4

          nucleophilic substitution (condensation)
          C

          reduction

           LiAlH4

          oxidation
          D

          hydrogenation

          H2

          addition

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            2
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            But-1-ene reacts separately with HBr and H2/ Ni to give products X and Z respectively. 

            What are the major products of the reactions?

              X Z
            A. CH2BrCH2CH2CH3 CH3CH2Cidentical toCH
            B. CH3CH2CH2CH2OH CH3CH2CH2CH3
            C. CH3CHBrCH2CH3 CH3CH2Cidentical toCH
            D. CH3CHBrCH2CH3 CH3CH2CH2CH3

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              3
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              Methylbenzene can be converted into 4-methylphenylamine in a multi-step reaction.

              Which order should the reagents be used to do this conversion? 

                1st reagent 2nd reagent 3rd reagent
              A. conc. HNO3 / conc. H2SO4 Sn / conc. HCl  NaOH
              B. Sn / conc. HCl conc. HNO3 / conc. H2SO4  NaOH
              C. Sn / conc. HCl  NaOH conc. HNO3 / conc. H2SO4
              D.  NaOH conc. HNO3 / conc. H2SO4 Sn / conc. HCl

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                4
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                Which alcohol could not be produced by the reduction of an aldehyde or a ketone?

                • 2,2-Dimethylbutan-1-ol

                • Propan-2-ol

                • 3-Methylpentan-3-ol

                • 2-Methylpentan-3-ol

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                5
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                Which molecule(s) can be both reduced by sodium borohydride, NaBH4, and oxidised by warm acidified potassium dichromate (VI)? 

                1. CH3CHBr(CH3)2CCHO
                2. CH3CHOHCH2CH3
                3. (CH3)3CCHO

                • I and II only 

                • I and III only 

                • II and III only 

                • I, II and III 

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