1.
Which three compounds can be considered to be a homologous series?
A.
CH3OH,
CH3CH2OH,
CH3CH2CH2OH
B.
CH3CH2OH,
C.
CH3CH2CH(OH)CH3,
CH3CH2CH2CH2OH,
D.
CH3CH2CH2CH2OH,
CH3CH2OCH2CH3,
CH3CHO,
CH3COOH
(CH3)3COH
(CH3)2CH2CHO
(Total 1 mark)
2.
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)
3.
Which three compounds can be considered to be a homologous series?
A.
CH3OH,
CH3CH2OH,
CH3CH2CH2OH
B.
CH3CH2OH,
C.
CH3CH2CH(OH)CH3,
CH3CH2CH2CH2OH,
D.
CH3CH2CH2CH2OH,
CH3CH2OCH2CH3,
CH3CHO,
CH3COOH
(CH3)3COH
(CH3)2CH2CHO
(Total 1 mark)
IB Questionbank Chemistry
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4.
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)
5.
Which compound is an amide?
A.
CH3COOCH3
B.
CH3CONH2
C.
CH3NH2
D.
CH2(NH2)COOH
(Total 1 mark)
6.
Draw the structural formula of the major organic products, A and B, formed in the following
reactions.
(a)
CH3CH2CH=CH2 + HBr → A
A:
(1)
IB Questionbank Chemistry
2
(b)
B:
(1)
(Total 2 marks)
7.
(a)
Describe the structure of benzene, C6H6.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(b)
State two pieces of evidence that support this description.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)
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8.
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)
9.
(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)
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10.
What is the product of the following reaction?
Ni
CH3CH2CH2CN + 2H2 
A.
CH3CH2CH2NH2
B.
CH3CH2CH2CH2NH2
C.
CH3CH2NH2
D.
CH3CH2CH2CH3
(Total 1 mark)
11.
The alkenes are an example of a homologous series.
(a)
State the name of the alkene shown.
......................................................................................................................................
(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)
IB Questionbank Chemistry
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(ii)
Draw the structural formula and state the name of the product formed.
...........................................................................................................................
(2)
(Total 4 marks)
12.
Consider the following sequence of reactions.
reaction2
reaction3
reaction1
RCH3 
 RCH2OH 
 RCOOH
 RCH2Br 
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)
IB Questionbank Chemistry
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(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)
13.
Which reaction pathway describes how ethanol can be formed?
A.
elimination
addition
  ethanol

 chloroethane 
ethene 
B.
nucleophilic substitution
substitution

 ethanol

 chloroethane 
ethane 
C.
substitution

 ethanol
ethene 
D.
addition

 ethanol
ethane 
(Total 1 mark)
14.
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)
IB Questionbank Chemistry
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15.
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)
16.
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)
17.
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)
18.
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.
IB Questionbank Chemistry
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State in the boxes below, the formulas of the organic substances needed to complete the
following reaction pathways.
(Total 4 marks)
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19.
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)
20.
(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)
21.
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)
IB Questionbank Chemistry
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22.
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)
23.
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)
IB Questionbank Chemistry
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24.
(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)
IB Questionbank Chemistry
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(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)
25.
How many isomers can exist for a compound with the molecular formula C2H2Cl2?
A.
1
B.
2
C.
3
D.
4
(Total 1 mark)
IB Questionbank Chemistry
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26.
What is the IUPAC name of CH3CH2CONH2?
A.
Aminopropanal
B.
Ethanamide
C.
Propylamine
D.
Propanamide
(Total 1 mark)
27.
Which is the correct classification of these alcohols?
1
2
1
2
3
3
A.
tertiary
secondary
primary
B.
tertiary
primary
secondary
C.
tertiary
tertiary
secondary
D.
secondary
primary
secondary
(Total 1 mark)
IB Questionbank Chemistry
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28.
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)
29.
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
(a)
Fig.2
Describe two different types of physical evidence which show that benzene does not
contain three double bonds.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
IB Questionbank Chemistry
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(b)
Explain how the reaction of benzene with bromine provides chemical evidence that
benzene does not contain three double bonds.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 3 marks)
30.
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)
31.
Alkenes can undergo electrophilic addition reactions with bromine and with hydrogen bromide.
(a)
Explain how a bromine molecule is able to act as an electrophile.
......................................................................................................................................
......................................................................................................................................
(1)
(b)
Name the product formed when but-2-ene reacts with
(i)
bromine.
...........................................................................................................................
(1)
(ii)
hydrogen bromide.
...........................................................................................................................
(1)
(Total 3 marks)
32.
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
IB Questionbank Chemistry
16
this reaction using curly arrows to represent the movement of electron pairs and explain clearly
why only one organic product is formed.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)
33.
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)
IB Questionbank Chemistry
17
(ii)
Explain the mechanism for this elimination reaction using curly arrows to represent the
movement of electron pairs.
(3)
(Total 4 marks)
IB Questionbank Chemistry
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34.
(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.
IB Questionbank Chemistry
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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)
35.
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)
36.
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)
37.
(i)
Chloroethene can be converted to ethanol in two steps. For each step deduce an overall
equation for the reaction taking place.
IB Questionbank Chemistry
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Step 1:
......................................................................................................................................
......................................................................................................................................
Step 2:
......................................................................................................................................
......................................................................................................................................
(2)
(ii)
State the reagents and conditions necessary to prepare ethanoic acid from ethanol in the
laboratory.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
(Total 7 marks)
IB Questionbank Chemistry
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38.
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)
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)
IB Questionbank Chemistry
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39.
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)
40.
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)
41.
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)
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42.
(a)
Identify all the major products, A–D, in the following reactions.
(i)
CH3COCl + CH3CH2NH2 → A + B
A:
B:
(1)
(ii)
2
H SO 4
+ 2HNO3 2

C + D + 2H2O
C:
D:
(1)
IB Questionbank Chemistry
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(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)
IB Questionbank Chemistry
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44.
(a)
Draw the structural formulas of the major organic products formed in the following
reactions.
(i)
H3CCH=CH2 + ICl →
(1)
(ii)
H3CCHO + HCN →
(1)
(iii)
(1)
(iv)
3


CH3MgI 
2. H O
1. H CCHO
2
IB Questionbank Chemistry
26
(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)
IB Questionbank Chemistry
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45.
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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(1)
(Total 2 marks)
IB Questionbank Chemistry
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46.
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)
47.
(i)
Describe a chemical test that could be used to distinguish between propane and propene.
In each case state the result of the test.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(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.
......................................................................................................................................
......................................................................................................................................
(2)
(iii) Other than polymerization, state one reaction of alkenes which is of economic importance.
......................................................................................................................................
......................................................................................................................................
(1)
(Total 5 marks)
IB Questionbank Chemistry
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48.
Propan-1-ol and propan-2-ol are two structural isomers of C3H8O.
(i)
State the equation for the complete combustion of C3H8O.
......................................................................................................................................
......................................................................................................................................
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(5)
(Total 10 marks)
49.
Which organic molecule is not a structural isomer of pentan-1-ol?
A.
pentan-2-ol
IB Questionbank Chemistry
30
B.
2-methylpentan-2-ol
C.
2-methylbutan-2-ol
D.
pentan-3-ol
(Total 1 mark)
50.
Which of the structures below is an aldehyde?
A.
CH3CH2CH2CH2OH
B.
CH3CH2COCH3
C.
CH3CH2COOCH3
D.
CH3CH2CH2CHO
(Total 1 mark)
51.
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)
IB Questionbank Chemistry
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52.
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 6 marks)
IB Questionbank Chemistry
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53.
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.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 5 marks)
54.
(a)
State the class of compounds to which the substance below belongs and deduce a
balanced equation for its reaction with aqueous sodium hydroxide.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
IB Questionbank Chemistry
33
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 4 marks)
55.
Deduce an equation for the reaction between propanoic acid and methanol. Identify the catalyst
and state the name of the organic compound, X, formed.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)
IB Questionbank Chemistry
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56.
What is the correct order of reaction types in the following sequence?
I C H OH 
II C H COOH 
III
C3H7Br 
 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)
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57.
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)
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58.
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)
59.
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.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)
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60.
Compare the rates of hydrolysis of the compounds below and suggest two reasons for the
difference in reactivity.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 3 marks)
61.
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)
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(ii)
Draw the structural formula of the organic compound that is produced by the hydrolysis
of this cyanohydrin.
(1)
(Total 2 marks)
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62.
State and explain whether the following molecules are primary, secondary or tertiary
halogenoalkanes.
E:
................................................................................................................................................
................................................................................................................................................
F:
................................................................................................................................................
................................................................................................................................................
G:
................................................................................................................................................
................................................................................................................................................
(Total 4 marks)
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63.
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)
64.
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.
Br 2
? X 
 1,2-dibromobutane
butan-2-ol 
(a)
State the name and draw the structural formula of X.
Name: ..........................................................................................................................
Structure:
(2)
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(b)
State an equation and the conditions needed for the conversion of butan-2-ol into X.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 9 marks)
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65.
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)
66.
Describe a chemical test that could be used to distinguish between pent-1-ene and pentane.
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
................................................................................................................................................
(Total 2 marks)
67.
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:
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B:
C:
IUPAC name: ..............................................................................................................
D:
(Total 5 marks)
68.
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.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(3)
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(b)
Describe two features of a homologous series.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
(Total 5 marks)
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