Organic Chem
Organic Chem
2.   What is the type of mechanism and an important feature of the reaction between C(CH3)3Br
     and aqueous NaOH?
                  Mechanism              Feature
     A.              SN1           a transition state
     B.              SN1           an intermediate
     C.              SN2           a transition state
     D.              SN2           an intermediate
                                                                                         (Total 1 mark)
I. 2-methylpentane
II. methylbutane
III. dimethylpropane
A. I and II only
     D.    I, II and III
                                                                                         (Total 1 mark)
4.   Which of the following pairs are members of the same homologous series?
     (a)   State and explain the trend of the boiling points of the first five members of the alkene
           homologous series.
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                                                                                                                                             (Total 5 marks)
6.   Below is a schematic diagram representing some reactions of ethene. The letters A–D represent
     the organic compounds formed from the reactants and catalysts shown.
     Deduce the structural formulas of compounds A, B, C, and D and state the IUPAC name of
     compound C.
     A:
B:
C:
D:
(Total 5 marks)
7. Describe a chemical test that could be used to distinguish between pent-1-ene and pentane.
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                                                                                                                                                 (Total 2 marks)
8.   State and explain whether the following molecules are primary, secondary or tertiary
     halogenoalkanes.
E:
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F:
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G:
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                                                                                                                                                 (Total 4 marks)
9.    Explain, using equations, the following steps in the free-radical mechanism of the reaction of
      methane with chlorine.
      •         Initiation
      •         Propagation
      •         Termination
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10.   Butan-2-ol cannot be directly converted to 1,2-dibromobutane. The conversion can be carried
      out in two stages by first converting butan-2-ol into X, which is then reacted with bromine.
                                                            Br2
                                                       ? X 
                                           butan-2-ol      1,2-dibromobutane
Name: ..........................................................................................................................
Structure:
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(b)   State an equation and the conditions needed for the conversion of butan-2-ol into X.
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(c)   Describe the mechanism of the second stage of the conversion, which occurs when
      bromine is added to X, using curly arrows to show the movement of electron pairs.
(3)
(d)   Butan-1-ol could be used instead of butan-2-ol. Compare the yield of 1,2-dibromobutane
      expected for butan-1-ol with that obtained for butan-2-ol. Explain your answer.
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                                                                                                                                        (Total 9 marks)
11.   Compare the rates of hydrolysis of the compounds below and suggest two reasons for the
      difference in reactivity.
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12.   State the formula of the product formed when 2-chloropropane reacts with magnesium to form
      a Grignard reagent and state the conditions required for this reaction to occur.
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13.   Grignard reagents are often used to increase the length of the hydrocarbon chain in molecules.
      An alternative way of doing this is to use cyanohydrins such as:
      (i)    State the reagents that react to produce this compound.
             ......................................................................................................................................
                                                                                                                                                           (1)
      (ii)   Draw the structural formula of the organic compound that is produced by the hydrolysis
             of this cyanohydrin.
                                                                                                                                                           (1)
                                                                                                                                               (Total 2 marks)
14.   (a)    State the class of compounds to which the substance below belongs and deduce a
             balanced equation for its reaction with aqueous sodium hydroxide.
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      (b)   Explain how the pH of an aqueous solution of the organic product from part (a) would
            compare with the pH of aqueous ammonia of the same concentration.
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                                                                                                                                              (Total 4 marks)
A. CH3CH=CHCHO
B. (CH3)2C=CHCH2OH
C. CH3OCH2CH3
      D.    CH3CHOHCH2CH3
                                                                                                                                               (Total 1 mark)
16.   The compounds H2NCH2CH2NH2 and HOOCCH2COOH react to form a polymer. What is the
      structure of the repeating unit of the polymer?
A. ( HNCH2CONHCH2CH2NHCO )
B. ( HNCH2CH2NHCOCH2CO )
C. ( OCCH2CONHCH2NHCO )
      D.     ( HNCH2CH2NHCOCH2NH )
                                                                                                                                               (Total 1 mark)
17.   Which two molecules are cis-trans isomers of each other?
A. X and Z
B. X and Y
C. W and Y
      D.    W and Z
                                                                               (Total 1 mark)
18. What is the correct order of reaction types in the following sequence?
                           I C H OH 
                   C3H7Br         II C H COOH 
                                                  III
                                                    C2H5COOC2H5
                              3 7        2 5
                      I                    II                     III
      A.       substitution           oxidation              condensation
      B.       addition               substitution           condensation
      C.       oxidation              substitution           condensation
      D.       substitution           oxidation              substitution
                                                                               (Total 1 mark)
19.   Two compounds, A and D, each have the formula C4H9Cl.
      Compound A is reacted with dilute aqueous sodium hydroxide to produce compound B with a
      formula of C4H10O. Compound B is then oxidized with acidified potassium manganate(VII) to
      produce compound C with a formula of C4H8O. Compound C resists further oxidation by
      acidified potassium manganate(VII).
      Compound D is reacted with dilute aqueous sodium hydroxide to produce compound E with a
      formula of C4H10O. Compound E does not react with acidified potassium manganate(VII).
A:
B:
C:
D:
E:
                                                                                        (Total 5 marks)
20.   Deduce an equation for the reaction between propanoic acid and methanol. Identify the catalyst
      and state the name of the organic compound, X, formed.
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                                                                                                                                                  (Total 4 marks)
C:
D:
E:
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21.   2-chloro-3-methylbutane reacts with sodium hydroxide via an SN2 mechanism.
      Explain the mechanism by using curly arrows to represent the movement of electron pairs.
(Total 4 marks)
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23.   Describe the mechanism for the reaction of water with ethanoyl chloride.
(Total 4 marks)
24.   (a)   Describe the mechanism for the reaction of benzene with chlorine, using curly arrows to
            show the movement of electron pairs, including the role of any other substance required
            for the reaction to occur.
                                                                                                        (4)
      (b)   Methylbenzene and nitrobenzene also react with chlorine under similar conditions.
            Explain the relative rates at which these two reactions occur.
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                                                                                                                                              (Total 6 marks)
A. pentan-2-ol
B. 2-methylpentan-2-ol
C. 2-methylbutan-2-ol
      D.    pentan-3-ol
                                                                                                                                               (Total 1 mark)
A. CH3CH2CH2CH2OH
B. CH3CH2COCH3
C. CH3CH2COOCH3
      D.    CH3CH2CH2CHO
                                                                                                                                               (Total 1 mark)
27.   What product is formed when CH3CH(OH)CH3 is reacted with acidified potassium
      dichromate(VI)?
A. CH3COOCH3
B. CH3CH2CHO
C. CH3CH2COOH
      D.    CH3COCH3
                                                                                                                                               (Total 1 mark)
28.   Which type of reaction occurs when 2-iodo-2-methylpropane, C(CH3)3I, reacts with aqueous
      sodium hydroxide, NaOH(aq)?
A. Addition
B. Free-radical substitution
C. SN1
      D.    SN2
                                                                                                                                               (Total 1 mark)
29.   (i)   Describe a chemical test that could be used to distinguish between propane and propene.
            In each case state the result of the test.
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                                                                                                                                                          (2)
      (ii)    Under certain conditions propene can polymerize to form poly(propene). State the type of
              polymerization taking place and draw a section of the polymer to represent the repeating
              unit.
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                                                                                                                                                            (2)
      (iii)   Other than polymerization, state one reaction of alkenes which is of economic
              importance.
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                                                                                                                                                            (1)
                                                                                                                                                (Total 5 marks)
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                                                                                                                                                            (2)
      (ii)    Both propan-1-ol and propan-2-ol can be oxidized in aqueous solution by potassium
              dichromate(VI). State any necessary conditions for the oxidation to occur and describe
              the colour change during the oxidation process.
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      (iii)   State the name(s) and structure(s) of the organic product(s) that can be formed when each
              of the alcohols is oxidized and suggest why one of the alcohols gives two organic
              products and the other only gives one organic product.
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                                                                                                                                              (Total 10 marks)
31.   Benzene, C6H6, is a planar compound which differs from the non-planar structure of
      cyclohexane, C6H12. The structures of benzene and the most stable form of cyclohexane are
      represented below.
      (a)       With reference to the compounds benzene, cyclohexane and 1,3-cyclohexadiene, state
                which compound would contain the shortest carbon-carbon bond length.
                ......................................................................................................................................
                                                                                                                                                              (1)
      (b)       Explain why it is more common for benzene to undergo substitution reactions than
                addition reactions.
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                                                                                                                                                              (1)
                                                                                                                                                  (Total 2 marks)
32.   Suggest why chloromethylbenzene, C6H5CH2Cl, reacts with warm aqueous sodium hydroxide,
      NaOH, easily whereas for chlorobenzene, C6H5Cl, stronger conditions such as high temperature
      (e.g. 350 °C) are needed.
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33.   (a)       Draw the structural formulas of the major organic products formed in the following
                reactions.
                                                                                                                                                              (1)
(ii)    H3CCHO + HCN →
(1)
(iii)
(1)
                1. H 3 CCHO
(iv)    CH3MgI     
                2. H O
                         
                    2
                              (1)
(b)   Draw the structural formula of the other product of the reaction in part (a) (i).
(1)
(c)   Identify each of the types of reaction in (a) as elimination, nucleophilic addition,
      electrophilic addition, acid-base, addition-elimination or Grignard.
              Reaction                                         Type
               (a) (i)
               (a) (ii)
               (a) (iii)
               (a) (iv)
                                                                                                         (4)
                                                                                             (Total 9 marks)
34.   Identify a suitable catalyst for the dehydration reaction of ethanol, CH3CH2OH, and describe
      and explain the mechanism of the reaction using curly arrows to represent the movement of
      electron pairs. State the name of the organic product formed.
Catalyst:
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Mechanism:
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                                                                                                                                                  (Total 4 marks)
35.   Deduce a two-step reaction pathway which can be used to convert butan-1-ol, CH3(CH2)3OH,
      into 1,2-dibromobutane, CH3CH2CHBrCH2Br. State the reagents used in each step and identify
      the product formed in step 1.
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36.   Halogenoalkanes can undergo SN1 and SN2 reactions with aqueous sodium hydroxide.
      Which halogenoalkane will react fastest with a 0.1 mol dm–3 solution of aqueous sodium
      hydroxide?
A. 2-chloro-2-methylpropane
B. 2-iodo-2-methylpropane
C. 1-chlorobutane
      D.    1-iodobutane
                                                                                           (Total 1 mark)
37.   Propanitrile can be prepared by reacting bromoethane with potassium cyanide. Which statement
      is not correct about the reaction between bromoethane and potassium cyanide?
(Total 1 mark)
40. There are several structural isomers with the molecular formula C5H11Br.
      (a)   Deduce the name of one of the isomers which can exist as enantiomers and draw
            three-dimensional representations of its two enantiomers.
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                                                                                                                                                          (3)
(b)   All the isomers react when warmed with a dilute aqueous solution of sodium hydroxide
      according to the equation below.
      (i)    The reaction with 1-bromopentane proceeds by an SN2 mechanism. Describe this
             mechanism using structural formulas and curly arrows to represent the movement
             of electron pairs.
(3)
                                                                                               (3)
(iii)   Explain why 1-bromopentane reacts by an SN2 mechanism whereas
        2-bromo-2-methylbutane reacts by an SN1 mechanism.
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                                                                                                                                      (3)
(iv)    Explain whether the boiling point of 1-bromopentane will be higher, lower or the
        same as that of 2-bromo-2-methylbutane.
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                                                                                                                                      (3)
(v)     The product C5H11OH formed from the reaction with 1-bromopentane is warmed
        with ethanoic acid in the presence of a few drops of concentrated sulfuric acid.
        State the name of the type of reaction taking place and the structural formula of the
        organic product.
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        ...........................................................................................................................
                                                                                                                                      (2)
      (c)   If the conditions of the reaction in (b) are changed so that a hot solution of sodium
            hydroxide in ethanol is used then a different reaction occurs. The reaction with
            2-bromo-2-methylbutane gives two different organic products. State the type of reaction
            taking place and suggest the identity (name or structure) of these two products.
            Explain whether or not they can exist as geometrical isomers.
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                                                                                                                                            (Total 21 marks)
41.   Dihalogenoalkanes can react with warm dilute potassium hydroxide solution to form diols.
      These diols can react with dicarboxylic acids.
      (i)   Deduce the equation for the reaction of benzene-1,4-dicarboxylic acid with the diol
            formed from 1,5-dibromopentane.
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      (ii)   Outline the economic importance of the reaction of diols with dicarboxylic acids.
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                                                                                                                                                           (1)
                                                                                                                                               (Total 4 marks)
42. (a) Identify all the major products, A–D, in the following reactions.
A:
B:
(1)
                                                H SO 4
             (ii)      2               + 2HNO3 2                             C +D +                2H2O
C:
D:
                                                                                                                                                           (1)
      (b)   C and D are isomers. Explain the mechanism of the reaction in (a) (ii), forming one of
            these two isomers, using curly arrows to represent the movement of electron pairs.
                                                                                                          (3)
                                                                                              (Total 5 marks)
43.   Benzene reacts with ethanoyl chloride, CH3COCl, in the presence of an aluminium chloride
      catalyst, AlCl3, in an acylation reaction. Explain the mechanism of the reaction, using curly
      arrows to represent the movement of electron pairs. Include the formation of the electrophile.
                                                                                              (Total 4 marks)
44.   Which is the best definition of structural isomers?
A. Compounds which have atoms with the same atomic numbers but different mass numbers
B. Compounds which have the same general formula but differ by a CH2 group
C. Compounds which have the same empirical formula but different molecular formulas
      D.    Compounds which have the same molecular formula but different arrangements of atoms
                                                                                          (Total 1 mark)
1 2 3
                     1                    2                     3
      A.        tertiary             secondary              primary
      B.        tertiary             primary                secondary
      C.        tertiary             tertiary               secondary
      D.        secondary            primary                secondary
                                                                                          (Total 1 mark)
46.   Which substances are possible products of the incomplete combustion of octane?
47. Which structure could represent a repeating unit of a polymer formed from propene?
A. ( CH2–CH(CH3) )
B. ( CH2–CH2–CH2 )
C. ( CH(CH3)–CH(CH3) )
      D.      ( CH2–CH2 )
                                                                                                                                                (Total 1 mark)
48.   Chloroethene, C2H3Cl, is an important organic compound used to manufacture the polymer
      poly(chloroethene).
(i) Draw the Lewis structure for chloroethene and predict the H – C– Cl bond angle.
             ......................................................................................................................................
                                                                                                                                                           (2)
                                                                                                                                                           (1)
      (iii)   Outline why the polymerization of alkenes is of economic importance and why the
              disposal of plastics is a problem.
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                                                                                                                                                (Total 5 marks)
49.   (i)     Chloroethene can be converted to ethanol in two steps. For each step deduce an overall
              equation for the reaction taking place.
Step 1:
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Step 2:
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                                                                                                                                                            (2)
      (ii)    State the reagents and conditions necessary to prepare ethanoic acid from ethanol in the
              laboratory.
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                                                                                                                                                            (2)
      (iii)   State an equation, including state symbols, for the reaction of ethanoic acid with water.
              Identify a Brønsted-Lowry acid in the equation and its conjugate base.
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                                                                                                                                                (Total 7 marks)
50.   Ethanol is part of the homologous series of alcohols. Describe two features of a homologous
      series.
                                                                                                                                                (Total 2 marks)
51.   (a)   (i)     Below are four structural isomers of alcohols with molecular formula C4H10O.
                    State the name of each of the isomers A, B, C and D.
(4)
            (ii)      Explain the mechanism named in part (b) (i) using curly arrows to represent the
                      movement of electron pairs.
                                                                                                                                                         (3)
                                                                                                                                            (Total 12 marks)
52.   When bromoethane reacts with magnesium in the presence of a non-polar solvent, a Grignard
      reagent is formed.
(a) Give the equation for the reaction of this Grignard reagent with water.
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            ......................................................................................................................................
                                                                                                                                                         (2)
      (b)   This Grignard reagent can also react with aldehydes and ketones to give an initial
            product which can then be hydrolysed by water to form an alcohol. State the names and
            formulas of the alcohols formed when the Grignard reagent reacts with
(i) ethanal.
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                                                                                                                                                         (2)
             (ii)      propanone.
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                                                                                                                                                           (2)
                                                                                                                                               (Total 6 marks)
53.   Alcohols can undergo elimination reactions in the presence of hot concentrated phosphoric
      acid.
(i) Name the organic product formed when butan-1-ol undergoes an elimination reaction.
             ......................................................................................................................................
                                                                                                                                                           (1)
      (ii)   Explain the mechanism for this elimination reaction using curly arrows to represent the
             movement of electron pairs.
                                                                                                                                                           (3)
                                                                                                                                               (Total 4 marks)
54.   Alkenes can undergo electrophilic addition reactions with bromine and with hydrogen bromide.
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            ......................................................................................................................................
                                                                                                                                                          (1)
(i) bromine.
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                                                                                                                                                          (1)
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                                                                                                                                              (Total 3 marks)
55.   When but-1-ene reacts with hydrogen bromide, two possible organic products could be formed
      but in practice only one organic product is obtained in high yield. Explain the mechanism for
      this reaction using curly arrows to represent the movement of electron pairs and explain clearly
      why only one organic product is formed.
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56.   Benzene is sometimes represented as containing three alternate double and single bonds (Fig.1)
      and sometimes represented as a hexagon with a circle in the middle (Fig.2).
                                                          Fig.1                                       Fig.2
      (a)   Describe two different types of physical evidence which show that benzene does not
            contain three double bonds.
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                                                                                                                                                          (2)
      (b)   Explain how the reaction of benzene with bromine provides chemical evidence that
            benzene does not contain three double bonds.
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            ......................................................................................................................................
                                                                                                                                                          (1)
                                                                                                                                              (Total 3 marks)
A. Aminopropanal
B. Ethanamide
C. Propylamine
      D.    Propanamide
                                                                                                                                               (Total 1 mark)
58.   What is the main organic product formed from the reaction of CH3CH2OH with
      CH3CH2CH2COOH in the presence of an acid catalyst?
A. Ethyl butanoate
B. Butyl ethanoate
C. Ethyl propanoate
      D.    Propyl ethanoate
                                                                                      (Total 1 mark)
I. Flavouring agents
II. Perfumes
III. Solvents
A. I and II only
      D.    I, II and III
                                                                                      (Total 1 mark)
60. How many isomers can exist for a compound with the molecular formula C2H2Cl2?
A. 1
B. 2
C. 3
      D.    4
                                                                                      (Total 1 mark)
61.   (a)   Below are four structural isomers with molecular formula C4H9Br. State the name of
            each of the isomers A, B, C and D.
(4)
      (b)   (i)     Identify the isomer(s) which will react with aqueous sodium hydroxide almost
                    exclusively by an SN1 mechanism. State the meaning of the symbols in the term
                    SN1 mechanism.
                                                                                                       (2)
            (ii)    Using the formula RBr to represent a bromoalkane, state an equation for the rate
                    determining step of this SN1 reaction.
                                                                                                       (1)
            (iii)   Identify one isomer that will react with aqueous sodium hydroxide almost
                    exclusively by an SN2 mechanism. Draw the mechanism for this reaction using
                    curly arrows to represent the movement of electron pairs. Include the structural
                    formulas of the transition state and the organic product.
                                                                                                       (4)
      (c)       State and explain how the rates of the reactions in parts (b) (i) and (b) (iii) are affected
                when the concentration of the sodium hydroxide is doubled.
                                                                                                                                                              (2)
      (d)       State and explain how the rate of reaction of 1-bromobutane with sodium hydroxide
                compares with that of 1-chlorobutane with sodium hydroxide.
                                                                                                                                                              (2)
      (e)       Identify the isomer of C4H9Br that can exist as stereoisomers. Outline how a polarimeter
                will distinguish between the isomers, and how their physical and chemical properties
                compare.
                                                                                                                                                              (5)
      (f)       (i)       State the type of reaction that occurs when isomer B, CH3CHBrCH2CH3, reacts
                          with a hot alcoholic solution of sodium hydroxide.
                                                                                                                                                              (1)
                (ii)      Explain how the reaction in part (f) (i) occurs by drawing the mechanism, using
                          curly arrows to represent the movement of electron pairs and identify the two
                          possible organic products.
                                                                                                                                                             (4)
                                                                                                                                                (Total 25 marks)
62.   Outline the different mechanisms involved in the manufacture of low-density poly(ethene) and
      high-density poly(ethene).
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63.   Methylbenzene can be prepared from benzene and iodomethane.
      State the catalyst used in this reaction and explain the mechanism of the reaction using curly
      arrows to represent the movement of electron pairs.
      Catalyst: ................................................................................................................................
                                                                                                                                                 (Total 4 marks)
64.   Methylbenzene reacts when heated with a mixture of concentrated sulfuric acid and
      concentrated nitric acid.
......................................................................................................................................
               ......................................................................................................................................
                                                                                                                                                             (1)
(ii) Identify the electrophile in this reaction and explain how it is formed.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
               ......................................................................................................................................
                                                                                                                                                             (3)
                                                                                                                                                 (Total 4 marks)
65.   What is the structural formula of 2,3-dibromo-3-methylhexane?
A. CH3CHBrCHBrCH(CH3)CH2CH3
B. CH3CHBrCBr(CH3)CH2CH2CH3
C. CH3CH2CHBrCBr(CH2CH3)2
      D.    CH3CHBrCHBrCH(CH2CH3)2
                                                                                          (Total 1 mark)
66.   What happens when a few drops of bromine water are added to excess hex-1-ene and the
      mixture is shaken?
II. The organic product formed does not contain any carbon-carbon double bonds.
A. I and II only
      D.    I, II and III
                                                                                          (Total 1 mark)
A. CH3COOH
B. CH3COCH3
C. CH3CH2COOH
      D.    CH3CH2CH3
                                                                                          (Total 1 mark)
68.   Alkenes are an economically and chemically important family of organic compounds.
      (i)     The reaction of alkenes with bromine water provides a test for unsaturation in the
              laboratory. Describe the colour change when bromine water is added to chloroethene.
                                                                                                            (1)
      (ii)    Deduce the Lewis structure of chloroethene and identify the formula of the repeating unit
              of the polymer poly(chloroethene).
                                                                                                            (2)
      (iii)   Besides polymerization, state two commercial uses of the reactions of alkenes.
                                                                                                            (2)
                                                                                                (Total 5 marks)
      (ii)    Deduce a reaction pathway for the two stages of the reaction. Your answer should
              include the fully balanced equation for each stage of the reaction and the reagents and
              conditions for the two stages.
                                                                                                            (5)
                                                                                                (Total 7 marks)
70.   (i)     Deduce the structural formulas of the two alcohol isomers of molecular formula C3H8O.
              Name each isomer and identify each as either a primary or a secondary alcohol.
                                                                                                            (3)
      (ii)    Oxidation of the alcohol isomers lead to the formation of different organic products.
              Determine the structures of the organic products formed from the oxidation of each
              alcohol isomer in (i) above and list the conditions required to obtain the different
              products.
                                                                                                            (5)
                                                                                                (Total 8 marks)
71.   Addition of hydrogen halides to unsymmetrical alkenes produces a mixture of halogenoalkanes.
      The latter can be converted into Grignard reagents by reaction with magnesium metal and then
      used for the preparation of various organic molecules with an increased number of carbon
      atoms.
      State in the boxes below, the formulas of the organic substances needed to complete the
      following reaction pathways.
                                                                                                (Total 4 marks)
72.   Describe, using equations and curly arrows to represent the movement of electron pairs, the
      mechanism of the reaction between propene and hydrogen bromide. Compare the relative
      stabilities of the two intermediate carbocations which lead to the formation of the major and
      minor products.
(Total 4 marks)
73. Hydrolysis of aliphatic and aromatic halides occurs under different conditions.
                                                                                              (Total 2 marks)
74.   Deduce a two-step reaction pathway for the conversion of butan-1-ol into 1,2-dibromobutane.
      State the appropriate equations, the reaction conditions and the reaction type for each step.
Step 1:
................................................................................................................................................
................................................................................................................................................
Step 2:
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 5 marks)
75.   The acidity of carboxylic acids depends on the carbon chain length and the nature of
      substituents in their molecules. Table 15 of the Data Booklet provides some examples.
      (a)       State and explain how the presence of halogen atoms in the hydrocarbon chain affects the
                acidity of carboxylic acids.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
                ......................................................................................................................................
                                                                                                                                                              (3)
      (b)       State how the acidity of 3-chloropropanoic acid compares to that of propanoic acid and
                chloroethanoic acid.
......................................................................................................................................
                ......................................................................................................................................
                                                                                                                                                              (1)
      (c)   Suggest the pKa value for 3-chloropropanoic acid.
            ......................................................................................................................................
                                                                                                                                                          (1)
                                                                                                                                              (Total 5 marks)
                                                                     H 2SO 4
                                        (CH3CH2)CH=CH(CH2CH3) + H2O    
                                                                         
A. CH3(CH2)2CH(OH)CH2CH3
B. CH3(CH2)5CH3
C. CH3(CH2)2CH(OSO3H)CH2CH3
      D.    CH3(CH2)6OH
                                                                                                                                               (Total 1 mark)
CH3(CH2)2COOCH3
A. Methyl butanoate
B. Butyl ethanoate
C. Butyl methanoate
      D.    Methyl propanoate
                                                                                                                                               (Total 1 mark)
78.   What is the product of the following reaction?
                                                                        Ni
                                                     CH3CH2CH2CN + 2H2 
A. CH3CH2CH2NH2
B. CH3CH2CH2CH2NH2
C. CH3CH2NH2
      D.    CH3CH2CH2CH3
                                                                                                                                               (Total 1 mark)
79. How many chiral carbon atoms are present in a molecule of 2,3-dibromobutane?
A. 1
B. 2
C. 3
      D.    4
                                                                                                                                               (Total 1 mark)
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                                          (2)
      (b)   1,3-dichlorocyclobutane exists as geometrical isomers, a form of stereoisomers.
                   ...........................................................................................................................
                                                                                                                                                       (2)
(ii) Identify the isomer with the higher boiling point and explain your reasoning.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
                   ...........................................................................................................................
                                                                                                                                                       (3)
                                                                                                                                           (Total 7 marks)
81.   Halogenoalkanes undergo two major types of reaction leading to the formation of different
      organic compounds.
82.   (i)    Describe the elimination of HBr from bromoethane. Your answer should include the
             reagents, conditions and equation for the reaction.
                                                                                                         (3)
      (ii)   Explain the mechanism for the elimination of HBr from bromoethane.
                                                                                                         (5)
                                                                                             (Total 8 marks)
83.   Alkylation of benzene is a common industrial process that allows substituents to be introduced
      into the aromatic ring.
      (a)    State an equation to show the reaction of benzene with chloromethane in the presence of
             a Lewis acid.
                                                                                                         (1)
      (b)   Describe, using equations and curly arrows to represent the movement of electron pairs,
            the mechanism of the above reaction.
                                                                                                          (4)
                                                                                              (Total 5 marks)
84.   When benzene undergoes alkylation, more than one substituent can be introduced into the
      aromatic ring. In contrast, acylation of methylbenzene usually gives a single organic product.
      (a)   State an equation, using structural formulas, to show the reaction of methylbenzene with
            ethanoyl chloride in the presence of a Lewis acid.
                                                                                                          (2)
      (b)      Give two reasons why other organic products do not form in this reaction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
               ......................................................................................................................................
                                                                                                                                                             (2)
                                                                                                                                                 (Total 4 marks)
85.   State the structural formulas of the two organic products formed in the reaction below and state
      the reaction type.
I. CH3(CH2)3CH3
II. (CH3)2CHCH3
III. CH3CH(CH3)CH2CH3
A. I and II only
      D.    I, II and III
                                                                                             (Total 1 mark)
87.   Which order is correct when the following substances are arranged in order of increasing
      boiling point?
A. CH3CH2Cl
B. CH2ClCH2Cl
C. CH2CHCl
      D.    CHClCHCl
                                                                                         (Total 1 mark)
                    addition              elimination
      A.    ethene     chloroethane      ethanol
                    substituti on
      C.    ethene        ethanol
                    addition
      D.    ethane     ethanol
                                                                                         (Total 1 mark)
90.   The alkenes are an example of a homologous series.
            ......................................................................................................................................
                                                                                                                                                          (1)
(b) Bromine water, Br2(aq), can be used to distinguish between the alkanes and the alkenes.
            (i)       Describe the colour change observed when the alkene shown in part (a) is added to
                      bromine water.
...........................................................................................................................
                      ...........................................................................................................................
                                                                                                                                                          (1)
(ii) Draw the structural formula and state the name of the product formed.
                      ...........................................................................................................................
                                                                                                                                                          (2)
                                                                                                                                              (Total 4 marks)
91.   The polymerization of the alkenes is one of the most significant reactions of the twentieth
      century.
(i) Outline two reasons why the polymers of the alkenes are of economic importance.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
              ......................................................................................................................................
                                                                                                                                                       (2)
(ii) State the type of polymerization reaction shown by the alkene below.
......................................................................................................................................
              ......................................................................................................................................
                                                                                                                                                       (1)
(iii) Deduce the structure of the resulting polymer showing three repeating units.
                                                                                                                                                       (1)
      (iv)   Explain why monomers are often gases or volatile liquids, but polymers are solids.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (2)
                                                                                                                                               (Total 6 marks)
92.   State the name of the product and identify the type of reaction which occurs between ethene
      and hydrogen chloride.
                                                                                                                                               (Total 2 marks)
      (a)    The alkane contains 81.7 % by mass of carbon. Determine its empirical formula, showing
             your working.
                                                                                                                                                           (3)
      (b)    Equal volumes of carbon dioxide and the unknown alkane are found to have the same
             mass, measured to an accuracy of two significant figures, at the same temperature and
             pressure. Deduce the molecular formula of the alkane.
                                                                                                                                                           (1)
      (c)    (i)       State the reagent and conditions needed for reaction 1.
                                                                                                                                                           (2)
             (ii)      Explain the mechanism of this reaction using curly arrows to show the movement
                       of electron pairs, and draw the structure of the transition state.
                                                                                                                                                          (3)
                                                                                                                                             (Total 16 marks)
      (ii)   Identify the isomer from part (i) which has the higher boiling point and explain your
             choice. Refer to both isomers in your explanation.
                                                                                                                                                           (2)
                                                                                                                                               (Total 4 marks)
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (3)
      (b)   State two pieces of evidence that support this description.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                                          (2)
                                                                                                                                              (Total 5 marks)
96.   Draw the structural formula of the major organic products, A and B, formed in the following
      reactions.
A:
(1)
(b)
B:
                                                                                                                                                          (1)
                                                                                                                                              (Total 2 marks)
97.   Deduce a two-step reaction pathway which can be used to convert 1-bromopropane into
      butanoic acid. Draw the structural formula of the organic product formed for each step and
      identify the reagents involved.
(Total 4 marks)
98.   Deduce a two-step reaction pathway which can be used to convert propan-2-ol into
      1,2-dibromopropane. Draw the structural formula of the organic product formed for each step
      and identify the reagents involved.
(Total 4 marks)
99. (a) State and explain which of the two compounds, phenol or ethanol, is the stronger acid.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                                          (2)
      (b)   State and explain which of the two compounds, ethanoic acid or chloroethanoic acid, is
            the stronger acid.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                                          (3)
                                                                                                                                              (Total 5 marks)
100. By which reactants and type of reaction can ethylamine (aminoethane) be produced?
A. CH3COOCH3
B. CH3CONH2
C. CH3NH2
      D.    CH2(NH2)COOH
                                                                                                                                               (Total 1 mark)
102. Which process can produce a polyester?
104. (a)    There are four structural isomers with the molecular formula C4H9Br. One of these
            structural isomers exists as two optical isomers. Draw diagrams to represent the
            three-dimensional structures of the two optical isomers.
                                                                                                           (2)
      (b)   All the isomers can by hydrolysed with aqueous sodium hydroxide solution. When the
            reaction of one of these isomers, X, was investigated the following kinetic data were
            obtained.
            (ii)    Determine the value of the rate constant for the reaction and state its units.
                                                                                                                 (2)
            (iv)    State equations for the steps that take place in the mechanism of this reaction and
                    state which of the steps is slow and which is fast.
                                                                                                              (2)
                                                                                                 (Total 11 marks)
105. The equation for the conversion of benzene into chlorobenzene in the presence of aluminium
     chloride is shown below.
                                                 AlCl 3
                                     C6H6 + Cl2   C6H5Cl + HCl
      Explain the mechanism of this reaction, using curly arrows to represent the movement of
      electron pairs.
                                                                                                     (Total 4 marks)
106. Deduce a two-step reaction pathway which can be used to convert methylbenzene into the
     molecule BrCH2(C6H4)Br shown below.
      Draw the structural formula of the organic product formed for the first step, identify the
      reagents involved and state any specific reaction conditions or catalysts.
(Total 3 marks)
107. (a) State the formulas of the products E and F formed in the following reaction.
CH3COCl + 2CH3CH2NH2 → E + F
E: .................................................................................................................................
            F: .................................................................................................................................
                                                                                                                                                          (2)
            ......................................................................................................................................
                                                                                                                                                          (1)
      (c)   State the type of reaction occurring in part (a).
            ......................................................................................................................................
                                                                                                                                                          (1)
                                                                                                                                              (Total 4 marks)
A. 1,1-dimethylpropane
B. 2-ethylpropane
C. 2-methylbutane
      D.    3-methylbutane
                                                                                                                                               (Total 1 mark)
110. When bromine water is shaken with a liquid organic compound, it is rapidly decolorized. What
     can be determined from this test?
A. I and II only
      D.      I, II and III
                                                                                                     (Total 1 mark)
112. Three compounds with similar relative molecular masses are butane, propanal and propan-1-ol.
      (i)     List the three compounds in order of increasing boiling point (lowest first) and explain
              the differences in their boiling points.
                                                                                                                (4)
      (ii)    Predict, with an explanation, which of the three compounds is least soluble or miscible in
              water.
                                                                                                                (2)
      (v)     Identify the class of alcohols that propan-2-ol belongs to and state the name of the
              organic product formed when it is oxidized by an acidified solution of potassium
              dichromate(VI).
                                                                                                             (2)
                                                                                                (Total 12 marks)
113. Ethanol can be formed from ethene in a two step reaction:
      (ii)    State the name of the reagent and the conditions used for step 2.
                                                                                                         (2)
      (iii)   The mechanism involved in step 2 is SN2. Explain how the reaction proceeds using curly
              arrows to represent the movement of electron pairs.
                                                                                                         (3)
      (iv)    Outline how ethanol is manufactured from ethene in industry and state one important
              commercial use of ethanol.
                                                                                                         (2)
                                                                                             (Total 8 marks)
114. (a)   Describe the structure of benzene.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
           ......................................................................................................................................
                                                                                                                                                         (4)
......................................................................................................................................
           ......................................................................................................................................
                                                                                                                                                         (1)
                                                                                                                                             (Total 5 marks)
115. (i)   State the structure of the organic product for the following reaction and name the
           mechanism for the reaction.
......................................................................................................................................
           ......................................................................................................................................
                                                                                                                                                         (2)
      (ii)   Explain why bromobenzene, C6H5Br, does not react with OH–.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (2)
                                                                                                                                               (Total 4 marks)
116. Magnesium is a very electropositive metal which can be used in the formation of Grignard
     reagents.
      (i)    State the product when bromomethane and magnesium react together in a non-polar
             solvent.
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (1)
(ii) Draw the structural formulas of the organic products formed in the following reactions.
                                 CH3CH2MgBr                      CO
                                                                 2
                                                                     
                                                                 H2O
                                             (CH ) 2 CO
                                 CH3CH2MgBr  3    
                                                      
                                                H2O
                                                                                                                                                           (2)
                                                                                                                                               (Total 3 marks)
117. Draw the structural formulas of the organic products, A–D, formed in the following reactions.
A:
B:
C:
D:
                                                                                           (Total 4 marks)
118. Elimination reactions are common for tertiary alcohols. State the organic product formed in this
     acid-catalysed reaction and explain the mechanism using curly arrows to show the movement of
     electron pairs.
(Total 4 marks)
A. Ester
B. Ketone
C. Aldehyde
      D.    Alcohol
                                                                                             (Total 1 mark)
A. Butanoic acid
B. Butanal
C. Methyl propanoate
      D.    Propyl methanoate
                                                                                             (Total 1 mark)
121. Which statements about substitution reactions are correct?
            III.   The reaction of sodium hydroxide with 1-chloropentane occurs at a slower rate
                   than with 1-bromopentane.
A. I and II only
      D.    I, II and III
                                                                                            (Total 1 mark)
122. What is the organic product of the reaction between methylamine and ethanoic acid?
A. CH3COONH4
B. CH3NHCOCH3
C. CH3COCH2NH2
      D.    CH3CH2CONH2
                                                                                            (Total 1 mark)
A. CH3CH2CHO
B. CH3CH2COCH3
C. CH3CH(CH3)2
      D.    CH3CH2CHOHCH3
                                                                                            (Total 1 mark)
124. (a)   But-1-ene and 1-aminobutane (1-butylamine) can both be prepared from 1-bromobutane.
           (i)     State the equation (using structural formulas) and the necessary reagents and
                   conditions for the preparation of but-1-ene from 1-bromobutane.
                                                                                                          (3)
           (ii)    Identify the type of reaction and explain the mechanism for the preparation of
                   but-1-ene from 1-bromobutane using curly arrows to represent the movement of
                   electron pairs.
                                                                                                          (3)
           (iii)   State the equation (using structural formulas) for the preparation of 1-aminobutane
                   from 1-bromobutane. State the necessary reagents and conditions of the reaction.
                                                                                                          (3)
           (iv)    Explain the mechanism for the preparation of 1-aminobutane from 1-bromobutane
                   using curly arrows to represent the movement of electron pairs.
                                                                                                          (4)
           (i)     Draw the structures of the two mirror images of the isomer that can exhibit optical
                   isomerism.
                                                                                                          (2)
           (ii)    Describe how the two optical isomers can be distinguished practically using
                   plane-polarized light.
                                                                                                          (2)
           (iii)   Explain why the mechanism of the reaction will be different if 1-bromobutane is
                   replaced by 2-bromo-2-methylpropane to form 2-amino-2-methylpropane in the
                   reaction in part (a)(iv).
                                                                                                          (3)
                                                                                             (Total 20 marks)
125. One form of nylon has the repeating unit:
      (ii)    Deduce the structures of the two monomers used to make this form of nylon.
                                                                                                                                                            (2)
              Deduce the equation for this reaction using n moles of each reactant.
                                                                                                                                                            (2)
                                                                                                                                                (Total 5 marks)
126. Benzene, C6H6, undergoes electrophilic substitution reactions in order to synthesize other
     compounds.
(i) Describe, using an equation, the formation of the electrophile in the nitration of benzene.
......................................................................................................................................
              ......................................................................................................................................
                                                                                                                                                            (2)
(ii)   Describe the stepwise mechanism for the reaction of benzene with ethanoyl chloride,
       CH3COCl in the presence of aluminium chloride, using curly arrows to show the
       movement of electron pairs.
                                                                                                  (3)
                                                                                      (Total 5 marks)
127. Chlorobenzene can be converted in two steps into the compound below.
     State the reagents and conditions required for each step and state the structure of the compound
     formed after the first step.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
     ................................................................................................................................................
                                                                                                                                                 (Total 3 marks)
128. (i) Methylbenzene can be converted in two steps into the compound below.
......................................................................................................................................
               ......................................................................................................................................
                                                                                                                                                             (2)
      (ii)   Deduce the formula of the product when the compound above reacts with hydroxide ions.
             Explain your answer.
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (2)
                                                                                                                                               (Total 4 marks)
A. But-2-ene
B. Butanoic acid
C. Butanal
      D.     Butanone
                                                                                                                                                (Total 1 mark)
A. CH3CH2CH2Br
B. CH3CH2CH(CH3)Cl
C. C(CH3)3Br
      D.     CH3CHClCH2CH3
                                                                                                                                                (Total 1 mark)
131. What is the IUPAC name of the following compound?
A. 2-methylbutane
B. Ethylpropane
C. 3-methylbutane
     D.    Pentane
                                                                       (Total 1 mark)
A. I and II only
     D.    I, II and III
                                                                       (Total 1 mark)
133. In some countries, ethanol is mixed with gasoline (petrol) to produce a fuel for cars called
     gasohol.
      (ii)    Use the information from Table 10 of the Data Booklet to determine the standard
              enthalpy change for the complete combustion of ethanol.
      (iii)   The standard enthalpy change for the complete combustion of octane, C8H18, is
              –5471 kJ mol–1. Calculate the amount of energy produced in kJ when 1 g of ethanol and
              1 g of octane is burned completely in air.
                                                                                                             (2)
      (iv)    Ethanol can be oxidized using acidified potassium dichromate, K2Cr2O7, to form two
              different organic products.
CH3CH2OH A B
              State the structural formulas of the organic products A and B and describe the conditions
              required to obtain a high yield of each of them.
                                                                                                             (4)
      (v)     Deduce and explain whether ethanol or A has the higher boiling point.
                                                                                                             (2)
      (vi)    Ethene can be converted into ethanol by direct hydration in the presence of a catalyst
              according to the following equation.
              For this reaction identify the catalyst used and state one use of the ethanol formed other
              than as a fuel.
                                                                                                             (2)
                                                                                                (Total 15 marks)
134. (i)     State the name of one structural isomer of pentane.
                                                                                                                                                           (1)
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (1)
      (b)    State and explain one piece of physical evidence and one piece of chemical evidence for
             the presence of delocalized electrons in the structure of benzene.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
             ......................................................................................................................................
                                                                                                                                                           (4)
                                                                                                                                               (Total 5 marks)
136. Describe and explain the relative rates of the reactions of hydroxide ions with chlorobenzene,
     C6H5Cl, and (chloromethyl)benzene, C6H5CH2Cl.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 3 marks)
137. Predict and explain the structures of the major and minor products when hydrogen bromide is
     added to 2-methylbut-2-ene, (CH3)2CCHCH3.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 5 marks)
138. Draw the structural formulas of the two elimination products formed when butan-2-ol,
     CH3CH2CH(OH)CH3 is heated with phosphoric acid.
(Total 2 marks)
139. (a) Outline the formation of a Grignard reagent. Include any necessary conditions.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                                          (2)
      (b)   2-methylbutan-2-ol is formed by the reaction of a ketone with a Grignard reagent.
            Draw the structural formula of 2-methylbutan-2-ol and deduce the structural formulas of
            the ketone and the Grignard reagent used for the reaction.
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                                          (3)
                                                                                                                                              (Total 5 marks)
140. What structural feature must a molecule have in order to undergo addition polymerization?
141. What is the organic product of the reaction between CH3CH2NH2 and CH3CH2COOH?
A. CH3CH2NHCOCH2CH3
B. CH3CH2CH2NHCOCH3
C. CH3CH2NHCOCH3
      D.    CH3NHCOCH3
                                                                                                                                               (Total 1 mark)
142. What is the IUPAC name of the compound CH3CH2COOCH2CH3?
A. Ethyl ethanoate
B. Propyl ethanoate
C. Ethyl propanoate
      D.    Pentyl propanoate
                                                                                                 (Total 1 mark)
144. Ethanol can be oxidized using acidified potassium dichromate, K2Cr2O7, to form two different
     organic products.
CH3CH2OH A B
      State the structural formulas of the organic products A and B and describe the conditions
      required to obtain a high yield of each of them.
                                                                                                (Total 4 marks)
145. Ethene can be converted into ethanol by direct hydration in the presence of a catalyst according
     to the following equation.
      For this reaction, identify the catalyst used and state one use of the ethanol formed other than as
      a fuel.
                                                                                                (Total 2 marks)
146. Deduce a two-step synthesis for each of the following conversions. For each step, state the
     structural formulas of all reactants and products and state the conditions used in the reactions.
      Explain the mechanism of this reaction using curly arrows to represent the movement of
      electron pairs.
                                                                                               (Total 3 marks)
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................................................................................................................................................
................................................................................................................................................
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................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 5 marks)
150. State the equation for the reaction of ethanoyl chloride, CH3COCl, with sodium hydroxide.
     Identify the mechanism for the reaction and explain it using curly arrows to show movement of
     electron pairs.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 5 marks)
151. How many structural isomers exist with the formula C3H5Cl3?
A. 3
B. 4
C. 5
      D.    6
                                                                                     (Total 1 mark)
152. Which substance is produced by the reaction of hydrogen with a vegetable oil?
A. Margarine
B. Nylon
C. Polypropene
      D.    Soap
                                                                                     (Total 1 mark)
A. CO2
B. CO
C. C
      D.    H2
                                                                                     (Total 1 mark)
154. Propene is converted to propanone in a two stage process.
Propene → X → Propanone
A. CH3CHBrCH3
B. CH3CH2CH2Br
C. CH3CHOHCH3
      D.    CH3CH2CH2OH
                                                                                                                                           (Total 1 mark)
155. (a)    The boiling points of the isomers of pentane, C5H12, shown are 10, 28 and 36 °C, but not
            necessarily in that order.
            (i)   Identify the boiling points for each of the isomers A, B and C and state a reason
                  for your answer.
                    Isomer                                A                               B                                C
                    Boiling point
...........................................................................................................................
                  ...........................................................................................................................
                                                                                                                                                      (3)
              (ii)      State the IUPAC names of isomers B and C.
B: .......................................................................................................................
                        C: .......................................................................................................................
                                                                                                                                                            (2)
      (b)     Both C5H12 and C5H11OH can be used as fuels. Predict which compound would release a
              greater amount of heat per gram when it undergoes complete combustion. Suggest two
              reasons to support your prediction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
              ......................................................................................................................................
                                                                                                                                                            (3)
                                                                                                                                                (Total 8 marks)
156. Halogenoalkanes can undergo substitution reactions with potassium hydroxide solution.
      (ii)    Substitution reactions may occur by either of two mechanisms namely SN1 or SN2.
              Outline the meaning of the term SN1.
                                                                                                                                                            (2)
      (iii)   Predict the mechanism (SN1 or SN2) expected for the reaction of the following
              halogenoalkanes with aqueous KOH.
              1-chlorobutane to form butan-1-ol
              2-chloro-2-methylpropane to form 2 methylpropan-2-ol.
                                                                                                                                                            (2)
     (iv)    Explain the mechanism of each reaction in part (iii) using curly arrows to represent the
             movement of electron pairs.
                                                                                                                                                          (6)
                                                                                                                                             (Total 11 marks)
157. (i)     Draw four structural isomers of molecular formula C4H10O which contain the –OH
             group.
                                                                                                                                                           (4)
     (ii)    On reaction with acidified potassium dichromate(VII), two of the isomers are oxidized in
             two steps to produce different products. Draw the structural formula of the two products
             formed from one of the isomers.
                                                                                                                                                           (2)
     (iii)   A third isomer is oxidized in one step. Draw the structural formula of the organic product
             formed.
                                                                                                                                                           (1)
     (iv)    State the colour change that takes place in these oxidation reactions.
                                                                                                                                                           (1)
     (v)     Identify the isomer which resists oxidation by acidified potassium dichromate(VI).
                                                                                                                                                           (1)
                                                                                                                                               (Total 9 marks)
158. Consider the two amines methylamine, CH3NH2, and dimethylamine, (CH3)2NH.
(a) Using Table 15 of the Data Booklet, state which of the amines is the more basic.
             ......................................................................................................................................
                                                                                                                                                           (1)
      (b)       Explain the relative basicities of the two amines.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
                ......................................................................................................................................
                                                                                                                                                              (2)
                                                                                                                                                  (Total 3 marks)
159. Explain why chloroethanoic acid is a stronger acid than ethanoic acid.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 2 marks)
160. Starting with chloromethane, outline one possible reaction pathway to synthesize ethanoic acid.
     Your answer should include:
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
      ................................................................................................................................................
                                                                                                                                                  (Total 2 marks)
161. The carbonyl chemistry of both aldehydes and ketones involves a number of different types of
     reactions.
(a) State the formulas of the products A and B, formed in the following reactions.
                                CH 3CH 2 MgBr
            (i)       (CH3)2CO       A
                                    H2O
                      A: ......................................................................................................................
                                                                                                                                                          (1)
(ii)
                      B: ......................................................................................................................
                                                                                                                                                          (1)
(b) State the type of reaction involved in the formation of B and H2O in (a)(ii).
            ......................................................................................................................................
                                                                                                                                                          (1)
                                                                                                                                              (Total 3 marks)
162. Alkenes commonly react by electrophilic addition reactions. Describe the mechanism of the
     following reaction, using curly arrows to show the movement of electron pairs, and suggest the
     reason for the formation of the major organic product, C.
CH2=CH(CH2CH3) + HI → C
......................................................................................................................................
            ......................................................................................................................................
                                                                                                                                              (Total 5 marks)
163. Alcohols can undergo elimination reactions. Describe the mechanism of the following reaction,
     using curly arrows to show the movement of electron pairs, and identify the organic product, D.
CH3CH2OH + H3PO4 → D
                                                                                                                                              (Total 5 marks)
164. Which reaction occurs via a free-radical mechanism?
165. Which compound could rotate the plane of polarization of polarized light?
A. (CH3)2CHCH2Cl
B. CH3CH2CH2CH2Cl
C. CH3CH2CHClCH3
      D.    (CH3)3CCl
                                                                                      (Total 1 mark)
166. What is the name of the ester formed when CH3CH2COOH and CH3OH react together?
A. Ethyl methanoate
B. Methyl ethanoate
C. Propyl methanoate
      D.    Methyl propanoate
                                                                                      (Total 1 mark)
167. Which formula represents a polyamide?
A. ( CH2–CHCl ) n
B. ( NH–(CH2)6–NH–CO–(CH3)4–CO ) n
C. ( CF2–CF2 ) n
      D.      ( O–(CH2)2–O–CO–         –CO ) n
                                                                                               (Total 1 mark)
      (i)     Draw the structural formulas of the two geometrical isomers of 1-chloro-but-2-ene.
                                                                                                          (2)
      (iii)   Draw the structural formula of one isomer of C4H7Cl that shows optical isomerism and
              identify the chiral carbon atom with an asterisk (*).
                                                                                                          (2)
                                                                                              (Total 5 marks)
169. The compound but-2-ene-1,4-dioic acid forms two geometrical isomers which have different
     physical and chemical properties.
      (i)     Explain the difference in the melting points of the two isomers.
                                                                                                          (3)
      (ii)    Outline how the two isomers behave differently when gently heated.
                                                                                                          (1)
                                                                                              (Total 4 marks)
170. The reaction between bromoethane, CH3CH2Br, and potassium cyanide is an example of a
     nucleophilic substitution reaction.
      (ii)    Explain the mechanism of the reaction using curly arrows to represent the movement of
              electron pairs.
                                                                                                           (4)
      (iii)   The organic product obtained in part (ii) can be reduced to form an amine.
              State an equation for the reaction, naming the catalyst involved.
                                                                                                           (2)
                                                                                               (Total 7 marks)
171. Bromoethane reacts with potassium hydroxide to undergo mainly a substitution reaction or an
     elimination reaction depending on the reaction conditions used.
      (i)     State an equation and the reaction conditions used to control the products formed in each
              case.
                                                                                                           (4)
      (ii)    Explain the mechanism of the elimination reaction using curly arrows to represent the
              movement of electron pairs.
                                                                                                           (4)
      (iii)   Under certain conditions, the major product obtained in the elimination reaction can
              undergo polymerization. Identify the type of polymerization this major product
              undergoes.
                                                                                                           (1)
                                                                                               (Total 9 marks)
172. Both benzene and methylbenzene undergo electrophilic substitution reactions.
     State the formulas of the reagents, E–G, including any catalysts used, in the following
     conversions.
E: ...........................................................................................................................................
F: ...........................................................................................................................................
      G: ...........................................................................................................................................
                                                                                                                                                  (Total 3 marks)
173. (i)        State whether –OH can be described as an activating or deactivating group with respect
                to aromatic electrophilic substitution reactions.
                ......................................................................................................................................
                                                                                                                                                              (1)
      (ii)    Describe the directing effect of –OH on a benzene ring in an aromatic electrophilic
              substitution reaction.
              ......................................................................................................................................
                                                                                                                                                            (1)
      (iii)   Explain the decreased reactivity due to the presence of the –NO2 group in an aromatic
              electrophilic substitution reaction.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
              ......................................................................................................................................
                                                                                                                                                            (2)
                                                                                                                                                (Total 4 marks)
174. Which statement about successive members of all homologous series is correct?
      D.    The boiling point of this compound would be higher than that of pentane.
                                                                                       (Total 1 mark)
176. Which compound forms when hydrogen bromide is added to but-2-ene?
A. 2-bromobutane
B. 2,3-dibromobutane
C. 1-bromobutane
      D.    1,2-dibromobutane
                                                                                          (Total 1 mark)
177. Which products can be potentially obtained from crude oil and are economically important?
                   I.       Plastics
                   II.      Margarine
                   III.     Motor fuel
A. I and II only
      D.    I, II and III
                                                                                          (Total 1 mark)
178. Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which products
     are most likely to be formed during this reaction?
.....................................................................................................................................
.....................................................................................................................................
           .....................................................................................................................................
                                                                                                                                                         (1)
     (b)   Ethanol and ethanoic acid can be distinguished by their melting points. State and explain
           which of the two compounds will have a higher melting point.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
           .....................................................................................................................................
                                                                                                                                                         (2)
(c) Draw the three isomers containing the alcohol functional group of formula C4H9OH.
                                                                                                                                                         (2)
                                                                                                                                             (Total 5 marks)
180. The following is a computer-generated representation of the molecule, methyl
     2-hydroxy benzoate, better known as oil of wintergreen.
      (i)     Deduce the empirical formula of methyl 2-hydroxy benzoate and draw the full structural
              formula, including any multiple bonds that may be present.
              The computer-generated representation shown does not distinguish between single and
              multiple bonds.
                                                                                                         (2)
      (ii)    In this representation, two of the carbon-oxygen bond lengths shown are 0.1424 nm and
              0.1373 nm. Explain why these are different and predict the carbon-oxygen bond length in
              carbon dioxide.
                                                                                                         (2)
      (ii)   Write an equation for the reaction between methane and chlorine to form chloromethane.
             Explain this reaction in terms of a free-radical mechanism.
                                                                                                                (5)
                                                                                                    (Total 7 marks)
182. (i)     Identify the formulas of the organic products, A–E, formed in the reactions, I–IV:
                                                              
                                           H      H
             I.     CH3(CH2)8OH + K2Cr2O7   A 
                                                   B
                                                   
                                          H
             III.   (CH3)2CHOH + K2Cr2O7   D
      (ii)   H2C=CH2 can react to form a polymer. Name this type of polymer and draw the
             structural formula of a section of this polymer consisting of three repeating units.
                                                                                                                (2)
                                                                                                    (Total 7 marks)
                                            Ni
                          CH3CH2CH2CN + H2 
A. CH3CH2CH2NH2
B. CH3CH2CH2CH3
C. CH3CH2CH2CH2CH3
      D.     CH3CH2CH2CH2NH2
                                                                                                    (Total 1 mark)
184. What is the correct IUPAC name for the following compound?
CH 3 CHCH 2 CH 2 CN
CH 3
A. 4-methylbutanenitrile
B. 4-methylpentanenitrile
C. 2-methylbutanenitrile
      D.    2-methylpentanenitrile
                                                                                             (Total 1 mark)
185. What is the organic product of the reaction between ethanol and ethanoic acid in the presence
     of sulfuric acid?
A. CH3CHO
B. CH3COOCH3
C. CH3CH2COOCH3
      D.    CH3COOCH2CH3
                                                                                             (Total 1 mark)
A. H2NCH2COOH
B. H3CCONH2
C. H3CCHBrI
      D.    HCOOCH3
                                                                                             (Total 1 mark)
187. The molecular formula, C3H4Cl2 represents several isomeric compounds. Some isomers are
     cyclic and some are unsaturated.
     (a)     Draw the structures of two cyclic compounds that are structural isomers and state the
             names of both isomers.
(2)
     (b)     Two of the non-cyclic compounds have geometrical isomers. Draw the structures of these
             compounds and their geometrical isomers.
                                                                                                           (2)
                                                                                               (Total 4 marks)
188. The compound, 2-bromobutane, CH3CHBrCH2CH3, can react with sodium hydroxide to form
     compounds F, G and H.
     Compound F, C4H10O, exists as a pair of optical isomers. Compounds G and H, C4H8, are
     structural isomers, and compound H exists as a pair of geometrical isomers.
     (ii)    Outline the use of a polarimeter in distinguishing between the optical isomers.
                                                                                                           (2)
     (iii)   Draw diagrams to show the shapes of the two geometrical isomers of H.
                                                                                                           (2)
      (iv)   Draw the mechanism, using curly arrows to represent the movement of electron pairs, to
             show the formation of G.
                                                                                                                                                           (3)
                                                                                                                                               (Total 9 marks)
189. A compound, J, has the molecular formula C2H4O2 and is obtained from a reaction between
     methanoic acid and methanol. Write an equation for this reaction and state the name of
     compound J.
                                                                                                                                               (Total 3 marks)
190. When hydrogen cyanide reacts with an aldehyde or a ketone the product molecule has one more
     carbon atom.
             .....................................................................................................................................
                                                                                                                                                           (1)
      (b)    Describe, using curly arrows, a mechanism for the reaction of hydrogen cyanide with
             propanone.
                                                                                                                                                           (4)
      (c)   Write an equation for the acid hydrolysis of this product. State the two functional groups
            in the organic product.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
            .....................................................................................................................................
                                                                                                                                                          (2)
                                                                                                                                              (Total 7 marks)
structure A structure B
      (a)   Use information from Table 9 of the Data Booklet to explain why structure B is used in
            preference to structure A.
.....................................................................................................................................
.....................................................................................................................................
.....................................................................................................................................
            .....................................................................................................................................
                                                                                                                                                          (2)
      (b)   The enthalpy changes for the hydrogenation of cyclohexene and benzene are as follows.
            (i)       Explain how this information can be used to support the statement that structure B
                      is more stable than structure A.
...........................................................................................................................
...........................................................................................................................
...........................................................................................................................
                      ...........................................................................................................................
                                                                                                                                                          (2)
...........................................................................................................................
                      ...........................................................................................................................
                                                                                                                                                          (1)
                                                                                                                                              (Total 5 marks)
            .....................................................................................................................................
                                                                                                                                                          (1)
(b) Complete the equation for this reaction using structural formulas for the products.
                                                 H2 N              H
                                                            N                              NO 2
O +
                                                                            NO 2
                                                                                                                                                          (2)
      (c)       State why the product from this particular reaction can be used to confirm that the
                reactant was cyclohexanone and not any other carbonyl compound.
.....................................................................................................................................
                .....................................................................................................................................
                                                                                                                                                              (1)
                                                                                                                                                  (Total 4 marks)
193. Explain how the presence of the –NO2 group on a benzene ring affects the rate of further
     substitution.
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
...............................................................................................................................................
      ...............................................................................................................................................
                                                                                                                                                  (Total 4 marks)