Chapter 10 Organic Chemistry HL - SL

1. Which of the following statements about alkenes is not correct?
A. They have reactive double bonds.
B. They can form addition polymers.
C. They react mainly by substitution.
D. They can react with water to form alcohols.

(Total 1 mark)
2. What is the type of mechanism and an important feature of the reaction

between C(CH3)3Br and aqueous NaOH?
Mechanism Feature
A. SN 1 a transition state
B. SN 1 an intermediate
C. SN 2 a transition state
D. SN 2 an intermediate
(Total 1 mark)
3. Which of the following are isomers of pentane?
I. 2-methylpentane
II. methylbutane
III. dimethylpropane
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
IB Questionbank Chemistry 1
4. Which of the following pairs are members of the same homologous series?
A. CH3CH2CH2OH and CH3CH2CHO
B. CH3CH(OH)CH3 and CH3CH2CH(OH)CH3
C. CH3COCH3 and CH3CH2COOH
D. CH3COCH2CH3 and CH3CH2CHO

(Total 1 mark)
5. Alkenes are important starting materials for a variety of products.
(a) State and explain the trend of the boiling points of the first five members of
the alkene homologous series.
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(3)
(b) Describe two features of a homologous series.
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(2)
(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:
IUPAC
name: ............................................................................................................
..
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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(Total 4 marks)
10. 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).
Deduce the structural formulas for compounds A, B, C, D and E.
A:
B:
C:
D:
E:
(Total 5 marks)
11. 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)
12. Which organic molecule is not a structural isomer of pentan-1-ol?
A. pentan-2-ol
B. 2-methylpentan-2-ol
C. 2-methylbutan-2-ol
D. pentan-3-ol
(Total 1 mark)
13. Which of the structures below is an aldehyde?
A. CH3CH2CH2CH2OH
B. CH3CH2COCH3
C. CH3CH2COOCH3
D. CH3CH2CH2CHO
(Total 1 mark)
14. 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)
15. 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. SN 1
D. SN 2
(Total 1 mark)
16. (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)
17. Propan-1-ol and propan-2-ol are two structural isomers of C3H8O.
(i) State the equation for the complete combustion of C3H8O.
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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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(3)
(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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(5)
(Total 10 marks)
18. 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)
19. An acidified solution of potassium dichromate is often used as an oxidizing
agent in organic chemistry. During the oxidation reaction of ethanol to ethanal
the dichromate ion is reduced to chromium(III) ions according to the following
unbalanced half-equation.
Cr2O72–(aq) + H+(aq) + e– → Cr3+(aq) + H2O(l)
(i) Describe the colour change that will be observed in the reaction.
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(1)
(ii) Deduce the oxidation number of chromium in Cr2O72–.
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(1)
(iii) State the balanced half-equation for the reduction of dichromate ions to
chromium(III) ions.
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(1)
(iv) Deduce the half-equation for the oxidation of ethanol to ethanal and hence
the overall redox equation for the oxidation of ethanol to ethanal by
acidified dichromate ions.
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(3)
(v) Explain why it is necessary to carry out the reaction under acidic
conditions.
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(1)
(vi) Identify the organic product formed if excess potassium dichromate is
used and the reaction is carried out under reflux.
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(1)
(Total 8 marks)
20. 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.
C5H11Br + NaOH → C5H11OH + NaBr
(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)
(ii) The reaction with 2-bromo-2-methylbutane proceeds by an SN1

mechanism.
Describe this mechanism using structural formulas and curly arrows
to represent the movement of electron pairs.
(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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(4)
(Total 21 marks)
21. 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)
22. Which is the correct classification of these alcohols?
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)
23. Which substances are possible products of the incomplete combustion of

octane?
A. Carbon dioxide and hydrogen gas
B. Carbon monoxide and water vapour
C. Carbon monoxide and hydrogen gas
D. Methane and hydrogen gas

(Total 1 mark)
24. 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)
25. 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.
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(2)
(ii) Draw a section of poly(chloroethene) containing six carbon atoms.
(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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(2)
(Total 5 marks)
26. (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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(3)
(Total 7 marks)
27. Ethanol is part of the homologous series of alcohols. Describe two features of a
homologous series.
(Total 2 marks)
28. (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) Determine the isomer that cannot be oxidized by acidified potassium

dichromate(VI), K2Cr2O7.
(1)
(iii) Determine the isomer which can be oxidized to butanal.

(1)
(iv) Determine the isomer which can be oxidized to butanone.

(1)
(v) Suggest the structural formula of another isomer of C4H10O.

(1)
(b) (i) Isomer A is formed by reacting 1-bromobutane with aqueous sodium
hydroxide.
State whether the reaction would proceed via an SN1 or SN2
mechanism.
(1)
(ii) Explain the mechanism named in part (b) (i) using curly arrows to
represent the movement of electron pairs.
(3)
(Total 12 marks)
29. 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)
30. What happens when a few drops of bromine water are added to excess hex-1-
ene and the mixture is shaken?
I. The colour of the bromine water disappears.
II. The organic product formed does not contain any carbon-carbon
double bonds.
III. 2-bromohexane is formed.
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
31. What is the product of the following reaction?
2 
Cr2 O 7 /H
CH3CH(OH)CH3    
A. CH3COOH
B. CH3COCH3
C. CH3CH2COOH
D. CH3CH2CH3
(Total 1 mark)
32. 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)
33. But-2-ene can be converted to butan-2-one in two stages.
(i) Draw the structural formulas of but-2-ene and butan-2-one.

(2)
(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)
34. (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)
35. What organic product is formed in the following reaction?

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)
36. Which of the following substances are structural isomers of each other?
I. CH3(CH2)3CH3
II. (CH3)2CHCH3
III. CH3CH(CH3)CH2CH3
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
37. Which order is correct when the following substances are arranged in order of
increasing boiling point?
A. CH3CH3 < CH3CHO < CH3CH2OH
B. CH3CHO < CH3CH2OH < CH3CH3
C. CH3CH2OH < CH3CH3 < CH3CHO
D. CH3CH3 < CH3CH2OH < CH3CHO

(Total 1 mark)
38. Which monomer could be used to form a polymer with the following repeating
unit?
A. CH3CH2Cl
B. CH2ClCH2Cl
C. CH2CHCl
D. CHClCHCl
(Total 1 mark)
39. Which reaction pathway describes how ethanol can be formed?

addition elimination
A. ethene    chloroethane    ethanol
substitution nucleophilic substitution

B. ethane     chloroethane    ethanol
substitution
C. ethene     ethanol
addition
D. ethane    ethanol
(Total 1 mark)
40. The alkenes are an example of a homologous series.
(a) State the name of the alkene shown.
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(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.
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(1)
(ii) Draw the structural formula and state the name of the product
formed.
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(2)
(Total 4 marks)
41. 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.
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(2)
(ii) State the type of polymerization reaction shown by the alkene below.
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(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.
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(2)
(Total 6 marks)
42. State the name of the product and identify the type of reaction which occurs
between ethene and hydrogen chloride.
(Total 2 marks)
43. Consider the following sequence of reactions.

reaction 1 reaction 2 reaction 3
RCH3   RCH2Br   RCH2OH   RCOOH
RCH3 is an unknown alkane in which R represents an alkyl group.
(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) State the reagent(s) and conditions needed for reaction 3.
(2)
(d) Reaction 1 involves a free-radical mechanism. Describe the stepwise
mechanism, by giving equations to represent the initiation, propagation
and termination steps.
(4)
(e) The mechanism in reaction 2 is described as SN2.
(i) State the meaning of each of the symbols in SN2.

(1)
(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)
44. Propan-1-ol has two structural isomers.
(i) Deduce the structural formula of each isomer.

(2)
(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)
45. Which three compounds can be considered to be a homologous series?
A. CH3OH, CH3CH2OH, CH3CH2CH2OH
B. CH3CH2OH, CH3CHO, CH3COOH
C. CH3CH2CH(OH)CH3, CH3CH2CH2CH2OH, (CH3)3COH
D. CH3CH2CH2CH2OH, CH3CH2OCH2CH3, (CH3)2CH2CHO

(Total 1 mark)
46. What is the IUPAC name for CH3CH2CH(CH3)CH3?
A. 1,1-dimethylpropane
B. 2-ethylpropane
C. 2-methylbutane
D. 3-methylbutane
(Total 1 mark)
47. When bromine water is shaken with a liquid organic compound, it is rapidly
decolorized. What can be determined from this test?
A. The compound is an alcohol.
B. The compound is an alkane.
C. The compound is an alkene.
D. The compound is an iodoalkane.

(Total 1 mark)
48. Which conditions are required to obtain a good yield of a carboxylic acid when
ethanol is oxidized using potassium dichromate(VI), K2Cr2O7(aq)?
I. Add sulfuric acid
II. Heat the reaction mixture under reflux
III. Distil the product as the oxidizing agent is added
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
49. 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)
(iii) When propan-1-ol is oxidized using a warm acidified solution of potassium

dichromate(VI) two different organic products can be obtained. Deduce the
name and structural formula for each of these two products.
(3)
(iv) Propan-2-ol is an isomer of propan-1-ol. Draw the structure of propan-2-ol.

(1)
(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)
50. Ethanol can be formed from ethene in a two step reaction:
(i) State the name of the reagent used for step 1.

(1)
(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)
51. What is the product of the oxidation of butan-2-ol?
A. But-2-ene
B. Butanoic acid
C. Butanal
D. Butanone
(Total 1 mark)
52. Which is a tertiary halogenoalkane?
A. CH3CH2CH2Br
B. CH3CH2CH(CH3)Cl
C. C(CH3)3Br
D. CH3CHClCH2CH3
(Total 1 mark)
53. What is the IUPAC name of the following compound?
A. 2-methylbutane
B. Ethylpropane
C. 3-methylbutane
D. Pentane
(Total 1 mark)
54. Which equations represent the incomplete combustion of methane?
I. CH4(g) + 2O2(g) → CO2(g) + 2H2O(g)
II. CH4(g) + 1½O2(g) → CO(g) + 2H2O(g)
III. CH4(g) + O2(g) → C(s) + 2H2O(g)
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
55. In some countries, ethanol is mixed with gasoline (petrol) to produce a fuel for
cars called gasohol.
(i) Define the term average bond enthalpy.

(2)
(ii) Use the information from Table 10 of the Data Booklet to determine the
standard enthalpy change for the complete combustion of ethanol.
CH3CH2OH(g) + 3O2(g) → 2CO2(g) + 3H2O(g)

(3)
(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.
C2H4(g) + H2O(g) CH3CH2OH(g)
For this reaction identify the catalyst used and state one use of the
ethanol formed other than as a fuel.
(2)
(Total 15 marks)
56. (i) State the name of one structural isomer of pentane.
(1)
(ii) Sodium hydroxide reacts with 1-bromopentane via an SN2 mechanism.

Describe the mechanism of this reaction using curly arrows to represent
the movement of electron pairs.
(4)
(Total 5 marks)
57. What structural feature must a molecule have in order to undergo addition
polymerization?
A. Two functional groups
B. A carbon–carbon double bond
C. Carbon atoms singly bonded together
D. A polar covalent bond

(Total 1 mark)
58. 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)
59. Ethene can be converted into ethanol by direct hydration in the presence of a
catalyst according to the following equation.
C2H4(g) + H2O(g) CH3CH2OH(g)
For this reaction, identify the catalyst used and state one use of the ethanol
formed other than as a fuel.
(Total 2 marks)
60. How many structural isomers exist with the formula C3H5Cl3?
A. 3
B. 4
C. 5
D. 6
(Total 1 mark)
61. Which substance is produced by the reaction of hydrogen with a vegetable oil?
A. Margarine
B. Nylon
C. Polypropene
D. Soap
(Total 1 mark)
62. Which substance is not produced during the combustion of alkanes?
A. CO2
B. CO
C. C
D. H2
(Total 1 mark)
63. Propene is converted to propanone in a two stage process.
Propene → X → Propanone
What is the formula of compound X?
A. CH3CHBrCH3
B. CH3CH2CH2Br
C. CH3CHOHCH3
D. CH3CH2CH2OH
(Total 1 mark)
64. (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
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(3)
(ii) State the IUPAC names of isomers B and C.
B: .........................................................................................................
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C: .........................................................................................................
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(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.
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(3)
(Total 8 marks)
65. Halogenoalkanes can undergo substitution reactions with potassium hydroxide

solution.
(i) State an equation for the reaction of C4H9Cl with KOH.

(1)
(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
(6)
(Total 11 marks)
66. (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)
67. Which statement about successive members of all homologous series is

correct?
A. They have the same empirical formula.
B. They differ by a CH2 group.
C. They have the same physical properties.
D. They differ in their degree of unsaturation.

(Total 1 mark)
68. The following is a three-dimensional representation of an organic molecule.
Which statement is correct?
A. The correct IUPAC name of the molecule is 2-methylpentane.
B. All the bond angles will be approximately 90°.
C. One isomer of this molecule is pentane.
D. The boiling point of this compound would be higher than that of pentane.
(Total 1 mark)
69. 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)
70. 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
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
71. Propane, C3H8, undergoes incomplete combustion in a limited amount of air.

Which products are most likely to be formed during this reaction?
A. Carbon monoxide and water
B. Carbon monoxide and hydrogen
C. Carbon dioxide and hydrogen
D. Carbon dioxide and water

(Total 1 mark)
72. (a) List two characteristics of a homologous series.
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(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.
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(2)
(c) Draw the three isomers containing the alcohol functional group of formula
C4H9OH.
(2)
(Total 5 marks)
73. 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)
(iii) Name all the functional groups present in the molecule.

(2)
(Total 6 marks)
74. (i) State and explain the trend in the boiling points of the first six alkanes
involving straight-chains.
(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)
75. (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
II. (CH3)3CBr + NaOH  C


H
III. (CH3)2CHOH + K2Cr2O7 
 D
IV. H2C=CH2 + Br2  E

(5)
(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)
76. Which molecule has a chiral centre?
A. CH3CH=CHCHO
B. (CH3)2C=CHCH2OH
C. CH3OCH2CH3
D. CH3CHOHCH2CH3
(Total 1 mark)
77. 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)
78. 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)
79. What is the correct order of reaction types in the following sequence?
I II III
C3H7Br  C3H7OH  C2H5COOH 
 C2H5COOC2H5
I II III
A. substitution oxidation condensation
B. addition substitution condensation
C. oxidation substitution condensation
D. substitution oxidation substitution
(Total 1 mark)
80. 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)
81. 1-chlorobutane can be converted to a pentylamine via a two stage process.
Deduce equations for each step of this conversion including any catalyst
required and name the organic product produced at each stage.
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(Total 5 marks)
82. Propanitrile can be prepared by reacting bromoethane with potassium cyanide.

Which statement is not correct about the reaction between bromoethane and
potassium cyanide?
A. The reaction is bi-molecular.
B. The reaction follows the SN2 mechanism.
C. Homolytic fission occurs between the carbon-bromine bond in
bromoethane.
D. The cyanide ion, :CN–, acts as a nucleophile.

(Total 1 mark)
83. Which reactants could be used to form the compound below?
A. Butanoic acid and ethanol
B. Propanoic acid and ethanol
C. Ethanoic acid and propan-1-ol
D. Ethanoic acid and butan-1-ol

(Total 1 mark)
84. Which compound is optically active?
(Total 1 mark)
85. 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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(3)
(ii) Outline the economic importance of the reaction of diols with dicarboxylic
acids.
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(1)
(Total 4 marks)
86. What is the IUPAC name of CH3CH2CONH2?
A. Aminopropanal
B. Ethanamide
C. Propylamine
D. Propanamide
(Total 1 mark)
87. 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)
88. What are some uses of esters?
I. Flavouring agents
II. Perfumes
III. Solvents
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
89. How many isomers can exist for a compound with the molecular formula
C2H2Cl2?
A. 1
B. 2
C. 3
D. 4
(Total 1 mark)
90. (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)
91. What is the IUPAC name for the following compound?
CH3(CH2)2COOCH3
A. Methyl butanoate
B. Butyl ethanoate
C. Butyl methanoate
D. Methyl propanoate
(Total 1 mark)
Ni
CH3CH2CH2CN + 2H2 
A. CH3CH2CH2NH2
B. CH3CH2CH2CH2NH2
C. CH3CH2NH2
D. CH3CH2CH2CH3
(Total 1 mark)
93. 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)
(Total 1 mark)
94. Existence of isomers leads to diversity of organic compounds.
(a) Describe what is meant by the term stereoisomers.
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(2)
(b) 1,3-dichlorocyclobutane exists as geometrical isomers, a form of
stereoisomers.
(i) Draw and name the two geometrical isomers of 1,3-

dichlorocyclobutane.
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(2)
(ii) Identify the isomer with the higher boiling point and explain your
reasoning.
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(3)
(Total 7 marks)
95. Halogenoalkanes undergo two major types of reaction leading to the formation
of different organic compounds.
(i) 1-bromopropane can be converted to 1-butylamine (butan-1-amine) in two

stages.
Draw the structural formulas of 1-bromopropane and 1-butylamine (butan-
1-amine).
(1)
(ii) Deduce a reaction pathway for the two-stage conversion of 1-

bromopropane to 1-butylamine (butan-1-amine). Your answer should
include an equation for each stage of the reaction and the reaction
conditions for the second stage.
(4)
(Total 5 marks)
96. (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)
97. By which reactants and type of reaction can ethylamine (aminoethane) be

produced?
Reactants Type of reaction

A. CH3Br + NH3 Nucleophilic substitution
B. CH3CH2Br + NH3 Reduction
C. CH3CN + H2 Nucleophilic substitution
D. CH3CN + H2 Reduction
(Total 1 mark)
98. Which compound is an amide?
A. CH3COOCH3
B. CH3CONH2
C. CH3NH2
D. CH2(NH2)COOH
(Total 1 mark)
99. Which process can produce a polyester?
A. Addition polymerization of a dicarboxylic acid
B. Condensation polymerization of a diol and a dicarboxylic acid
C. Addition polymerization of a diol and dicarboxylic acid
D. Condensation polymerization of a dicarboxylic acid

(Total 1 mark)
D100. Which statement about stereoisomers is correct?
A. 1,2-dichloroethane has two geometrical isomers.
B. 1,2-dichloroethane has two optical isomers.
C. 1,2-dichloroethene has two geometrical isomers.
D. 1,2-dichloroethene has two optical isomers.

(Total 1 mark)
101. (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.
Experime Initial [X] / Initial [OH–] / Initial rate of

nt mol dm–3 mol dm–3 reaction /
mol dm–3 min–1
1 2.0 × 10–2 2.0 × 10–2 4.0 × 10–3
2 2.0 × 10–2 4.0 × 10–2 4.0 × 10–3
3 4.0 × 10–2 4.0 × 10–2 8.0 × 10–3
(i) Deduce the rate expression for the reaction.
(3)
(ii) Determine the value of the rate constant for the reaction and state its
units.
(2)
(iii) State the name of isomer X and explain your choice.

(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)
102. Identify the functional group present in HCOCH2CH3.
A. Ester
B. Ketone
C. Aldehyde
D. Alcohol
(Total 1 mark)
103. What is the IUPAC name for HCOOCH2CH2CH3?
A. Butanoic acid
B. Butanal
C. Methyl propanoate
D. Propyl methanoate
(Total 1 mark)
104. Which statements about substitution reactions are correct?
I. The reaction between sodium hydroxide and 1-chloropentane

predominantly follows an SN2 mechanism.
II. The reaction between sodium hydroxide and 2-chloro-2-

methylbutane predominantly follows an SN2 mechanism.
III. The reaction of sodium hydroxide with 1-chloropentane occurs at a

slower rate than with 1-bromopentane.
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
105. What is the organic product of the reaction between methylamine and ethanoic
acid?
A. CH3COONH4
B. CH3NHCOCH3
C. CH3COCH2NH2
D. CH3CH2CONH2
(Total 1 mark)
106. Which compound can exist as stereoisomers?
A. CH3CH2CHO
B. CH3CH2COCH3
C. CH3CH(CH3)2
D. CH3CH2CHOHCH3
(Total 1 mark)
107. (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
(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)
(b) 2-bromobutane and 2-bromo-2-methylpropane are two isomers of 1-

bromobutane.
(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)
108. One form of nylon has the repeating unit:
(i) Identify the circled functional group.

(1)
(ii) Deduce the structures of the two monomers used to make this form of
nylon.
(2)
(iii) Nylon is a condensation polymer. Another condensation polymer can be

formed by reacting ethane-1,2-diol with benzene-1,4-dicarboxylic acid.
Deduce the equation for this reaction using n moles of each reactant.
(2)
(Total 5 marks)
109. What is the organic product of the reaction between CH3CH2NH2 and
CH3CH2COOH?
A. CH3CH2NHCOCH2CH3
B. CH3CH2CH2NHCOCH3
C. CH3CH2NHCOCH3
D. CH3NHCOCH3
(Total 1 mark)
110. What is the IUPAC name of the compound CH3CH2COOCH2CH3?
A. Ethyl ethanoate
B. Propyl ethanoate
C. Ethyl propanoate
D. Pentyl propanoate
(Total 1 mark)
111. Which statement is correct about the enantiomers of a chiral compound?
A. Their physical properties are different.
B. All their chemical reactions are identical.
C. A racemic mixture will rotate the plane of polarized light.
D. They will rotate the plane of polarized light in opposite directions.

(Total 1 mark)
112. 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.
(i) Ethanol to ethyl ethanoate.

(2)
(ii) Propene to propanone.

(2)
(Total 4 marks)
113. The reagents used in an elimination reaction are shown below.
Explain the mechanism of this reaction using curly arrows to represent the
movement of electron pairs.
(Total 3 marks)
114. (i) Describe geometrical isomerism.

(1)
(ii) Draw the geometrical isomers of but-2-ene.

(2)
(iii) Draw the two enantiomers of butan-2-ol.

(2)
(Total 5 marks)
115. Which reaction occurs via a free-radical mechanism?
A. C2H6 + Br2 → C2H5Br + HBr
B. C2H4 + Br2 → C2H4Br2
C. C4H9I + OH– → C4H9OH + I–
D. (CH3)3CI + H2O → (CH3)3COH + HI

(Total 1 mark)
116. Which compound could rotate the plane of polarization of polarized light?
A. (CH3)2CHCH2Cl
B. CH3CH2CH2CH2Cl
C. CH3CH2CHClCH3
D. (CH3)3CCl
(Total 1 mark)
117. 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)
118. 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)
119. The compound C4H7Cl can exhibit stereoisomerism.
(i) Draw the structural formulas of the two geometrical isomers of 1-chloro-
but-2-ene.
(2)
(ii) Explain why 1-chloro-but-2-ene shows geometrical isomerism.
(1)
(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)
120. 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)
121. The reaction between bromoethane, CH3CH2Br, and potassium cyanide is an

example of a nucleophilic substitution reaction.
(i) State whether this reaction is SN1 or SN2.

(1)
(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)
122. 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
(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)

Ni
CH3CH2CH2CN + H2 
A. CH3CH2CH2NH2
B. CH3CH2CH2CH3
C. CH3CH2CH2CH2CH3
D. CH3CH2CH2CH2NH2
(Total 1 mark)
124. What is the correct IUPAC name for the following compound?
CH 3CHCH 2CH 2CN
CH 3
A. 4-methylbutanenitrile
B. 4-methylpentanenitrile
C. 2-methylbutanenitrile
D. 2-methylpentanenitrile
(Total 1 mark)
125. 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)
126. Which compound can exist as optical isomers?
A. H2NCH2COOH
B. H3CCONH2
C. H3CCHBrI
D. HCOOCH3
(Total 1 mark)
127. 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)
128. 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.
(i) Draw the structures of the two optical isomers of F.

(2)
(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)
129. 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)

Chapter 10 Organic Chemistry HL - SL

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Chapter 10 Organic Chemistry HL - SL

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1. Which of the following statements about alkenes is not correct?

A. They have reactive double bonds.

B. They can form addition polymers.

C. They react mainly by substitution.

D. They can react with water to form alcohols.

2. What is the type of mechanism and an important feature of the reaction

3. Which of the following are isomers of pentane?

B. I and III only

C. II and III only

A. CH3CH2CH2OH and CH3CH2CHO

B. CH3CH(OH)CH3 and CH3CH2CH(OH)CH3

C. CH3COCH3 and CH3CH2COOH

D. CH3COCH2CH3 and CH3CH2CHO

5. Alkenes are important starting materials for a variety of products.

(b) Describe two features of a homologous series.

Deduce the structural formulas of compounds A, B, C, and D and state the

7. Describe a chemical test that could be used to distinguish between pent-1-ene

Compound A is reacted with dilute aqueous sodium hydroxide to produce

Compound D is reacted with dilute aqueous sodium hydroxide to produce

Deduce the structural formulas for compounds A, B, C, D and E.

12. Which organic molecule is not a structural isomer of pentan-1-ol?

13. Which of the structures below is an aldehyde?

15. Which type of reaction occurs when 2-iodo-2-methylpropane, C(CH3)3I, reacts

(iii) Other than polymerization, state one reaction of alkenes which is of

17. Propan-1-ol and propan-2-ol are two structural isomers of C3H8O.

(i) State the equation for the complete combustion of C3H8O.

(ii) Both propan-1-ol and propan-2-ol can be oxidized in aqueous solution by

Cr2O72–(aq) + H+(aq) + e– → Cr3+(aq) + H2O(l)

(ii) Deduce the oxidation number of chromium in Cr2O72–.

C5H11Br + NaOH → C5H11OH + NaBr

(i) The reaction with 1-bromopentane proceeds by an SN2 mechanism.

(ii) The reaction with 2-bromo-2-methylbutane proceeds by an SN1

(iii) Explain why 1-bromopentane reacts by an SN2 mechanism whereas

(iv) Explain whether the boiling point of 1-bromopentane will be higher,

21. Which is the best definition of structural isomers?

C. Compounds which have the same empirical formula but different

D. Compounds which have the same molecular formula but different

23. Which substances are possible products of the incomplete combustion of

A. Carbon dioxide and hydrogen gas

B. Carbon monoxide and water vapour

C. Carbon monoxide and hydrogen gas

D. Methane and hydrogen gas

25. Chloroethene, C2H3Cl, is an important organic compound used to manufacture

(ii) Draw a section of poly(chloroethene) containing six carbon atoms.

(ii) Determine the isomer that cannot be oxidized by acidified potassium

(iii) Determine the isomer which can be oxidized to butanal.

(iv) Determine the isomer which can be oxidized to butanone.

(v) Suggest the structural formula of another isomer of C4H10O.

29. What is the structural formula of 2,3-dibromo-3-methylhexane?

I. The colour of the bromine water disappears.

III. 2-bromohexane is formed.

B. I and III only

C. II and III only

32. Alkenes are an economically and chemically important family of organic

(iii) Besides polymerization, state two commercial uses of the reactions of

33. But-2-ene can be converted to butan-2-one in two stages.

(i) Draw the structural formulas of but-2-ene and butan-2-one.

35. What organic product is formed in the following reaction?

B. I and III only

C. II and III only

A. CH3CH3 < CH3CHO < CH3CH2OH

B. CH3CHO < CH3CH2OH < CH3CH3

C. CH3CH2OH < CH3CH3 < CH3CHO