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B.
C.
D.
2.
What is the type of mechanism and an important feature of the reaction between C(CH 3)3Br and
aqueous NaOH?
Mechanism
Feature
A.
SN1
a transition state
B.
SN1
an intermediate
C.
SN2
a transition state
D.
SN2
an intermediate
(Total 1 mark)
3.
2-methylpentane
II.
methylbutane
III.
dimethylpropane
A.
I and II only
B.
C.
D.
I, II and III
(Total 1 mark)
IB Questionbank Chemistry
4.
Which of the following pairs are members of the same homologous series?
A.
B.
C.
D.
5.
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)
IB Questionbank Chemistry
6.
Deduce the structural formulas of compounds A, B, C, and D and state the IUPAC
name of compound C.
IB Questionbank Chemistry
A:
B:
C:
D:
(Total 5 marks)
7.
Describe a chemical test that could be used to distinguish between pent-1-ene and
pentane.
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(Total 2 marks)
IB Questionbank Chemistry
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)
IB Questionbank Chemistry
IB Questionbank Chemistry
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.
pentan-2-ol
B.
2-methylpentan-2-ol
C.
2-methylbutan-2-ol
D.
pentan-3-ol
(Total 1 mark)
IB Questionbank Chemistry
11.
CH3CH2CH2CH2OH
B.
CH3CH2COCH3
C.
CH3CH2COOCH3
D.
CH3CH2CH2CHO
(Total 1 mark)
12.
CH3COOCH3
B.
CH3CH2CHO
C.
CH3CH2COOH
D.
CH3COCH3
(Total 1 mark)
13.
Addition
B.
Free-radical substitution
C.
S N1
D.
S N2
(Total 1 mark)
IB Questionbank Chemistry
14.
(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)
(iii)
15.
IB Questionbank Chemistry
IB Questionbank Chemistry
10
(ii)
(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)
IB Questionbank Chemistry
11
IB Questionbank Chemistry
12
16.
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)
17.
2
1
3
3
A.
tertiary
secondary
primary
B.
tertiary
primary
secondary
C.
tertiary
tertiary
secondary
D.
secondary
primary
secondary
(Total 1 mark)
IB Questionbank Chemistry
13
18.
B.
C.
D.
19.
Which structure could represent a repeating unit of a polymer formed from propene?
A.
( CH2CH(CH3) )
B.
( CH2CH2CH2 )
C.
( CH(CH3)CH(CH3) )
D.
( CH2CH2 )
(Total 1 mark)
20.
Draw the Lewis structure for chloroethene and predict the H C Cl bond angle.
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(2)
IB Questionbank Chemistry
14
(ii)
(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)
21.
(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)
IB Questionbank Chemistry
15
(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 Brnsted-Lowry acid in the equation and its conjugate base.
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(3)
(Total 7 marks)
22.
IB Questionbank Chemistry
16
23.
(a)
(i)
(4)
(ii)
(iii)
(iv)
IB Questionbank Chemistry
17
(v)
(b)
(i)
(ii)
Explain the mechanism named in part (b) (i) using curly arrows to represent
the movement of electron pairs.
(3)
(Total 12 marks)
24.
CH3CHBrCHBrCH(CH3)CH2CH3
B.
CH3CHBrCBr(CH3)CH2CH2CH3
C.
CH3CH2CHBrCBr(CH2CH3)2
D.
CH3CHBrCHBrCH(CH2CH3)2
(Total 1 mark)
IB Questionbank Chemistry
18
25.
What happens when a few drops of bromine water are added to excess hex-1-ene and
the mixture is shaken?
I.
II.
The organic product formed does not contain any carbon-carbon double
bonds.
III.
2-bromohexane is formed.
A.
I and II only
B.
C.
D.
I, II and III
(Total 1 mark)
26.
Cr2 O 7 /H
CH3CH(OH)CH3
A.
CH3COOH
B.
CH3COCH3
C.
CH3CH2COOH
D.
CH3CH2CH3
(Total 1 mark)
27.
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)
IB Questionbank Chemistry
19
(iii)
28.
(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)
29.
(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)
IB Questionbank Chemistry
20
30.
CH3(CH2)3CH3
II.
(CH3)2CHCH3
III.
CH3CH(CH3)CH2CH3
A.
I and II only
B.
C.
D.
I, II and III
(Total 1 mark)
31.
Which order is correct when the following substances are arranged in order of
increasing boiling point?
A.
B.
C.
D.
IB Questionbank Chemistry
21
32.
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)
33.
addition
elimination
ethene chloroethane ethanol
B.
substitution
nucleophilic substitution
ethane chloroethane ethanol
C.
substitution
ethene ethanol
D.
addition
ethane ethanol
(Total 1 mark)
IB Questionbank Chemistry
22
34.
.................................................................................................................................
.....
(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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...
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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)
IB Questionbank Chemistry
23
35.
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)
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(1)
(iii)
Deduce the structure of the resulting polymer showing three repeating units.
(1)
IB Questionbank Chemistry
24
(iv)
Explain why monomers are often gases or volatile liquids, but polymers are
solids.
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(2)
(Total 6 marks)
36.
State the name of the product and identify the type of reaction which occurs between
ethene and hydrogen chloride.
(Total 2 marks)
37.
(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)
(ii)
IB Questionbank Chemistry
25
(2)
(d)
(e)
(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)
38.
(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)
39.
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
26
40.
1,1-dimethylpropane
B.
2-ethylpropane
C.
2-methylbutane
D.
3-methylbutane
(Total 1 mark)
41.
B.
C.
D.
42.
Which conditions are required to obtain a good yield of a carboxylic acid when ethanol
is oxidized using potassium dichromate(VI), K2Cr2O7(aq)?
I.
II.
III.
A.
I and II only
B.
C.
D.
I, II and III
(Total 1 mark)
IB Questionbank Chemistry
27
43.
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)
(iii)
(iv)
(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)
44.
(i)
(ii)
State the name of the reagent and the conditions used for step 2.
(2)
IB Questionbank Chemistry
28
(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)
45.
But-2-ene
B.
Butanoic acid
C.
Butanal
D.
Butanone
(Total 1 mark)
46.
CH3CH2CH2Br
B.
CH3CH2CH(CH3)Cl
C.
C(CH3)3Br
D.
CH3CHClCH2CH3
(Total 1 mark)
IB Questionbank Chemistry
29
47.
A.
2-methylbutane
B.
Ethylpropane
C.
3-methylbutane
D.
Pentane
(Total 1 mark)
48.
II.
III.
A.
I and II only
B.
C.
D.
I, II and III
(Total 1 mark)
IB Questionbank Chemistry
30
49.
In some countries, ethanol is mixed with gasoline (petrol) to produce a fuel for cars
called gasohol.
(i)
(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
1
(iv)
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)
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)
IB Questionbank Chemistry
31
50.
(i)
(ii)
51.
B.
C.
D.
6
(Total 1 mark)
52.
Margarine
B.
Nylon
C.
Polypropene
D.
Soap
(Total 1 mark)
IB Questionbank Chemistry
32
53.
CO2
B.
CO
C.
D.
H2
(Total 1 mark)
54.
CH3CHBrCH3
B.
CH3CH2CH2Br
C.
CH3CHOHCH3
D.
CH3CH2CH2OH
(Total 1 mark)
55.
(a)
The boiling points of the isomers of pentane, C5H12, shown are 10, 28 and 36 C,
but not necessarily in that order.
IB Questionbank Chemistry
33
(i)
Identify the boiling points for each of the isomers A, B and C and state a
reason for your answer.
Isomer
Boiling point
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...
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...
(3)
(ii)
(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)
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34
56.
IB Questionbank Chemistry
35
(ii)
(iii)
Predict the mechanism (SN1 or SN2) expected for the reaction of the following
halogenoalkanes with aqueous KOH.
1-chlorobutane to form butan-1-ol
2-chloro-2-methylpropane to form 2 methylpropan-2-ol.
(2)
(iv)
Explain the mechanism of each reaction in part (iii) using curly arrows to
represent the movement of electron pairs.
(6)
(Total 11 marks)
57.
(i)
Draw four structural isomers of molecular formula C4H10O which contain the OH
group.
(4)
(ii)
(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)
IB Questionbank Chemistry
36
58.
B.
C.
D.
59.
IB Questionbank Chemistry
37
B.
C.
D.
The boiling point of this compound would be higher than that of pentane.
(Total 1 mark)
60.
2-bromobutane
B.
2,3-dibromobutane
C.
1-bromobutane
D.
1,2-dibromobutane
(Total 1 mark)
61.
Which products can be potentially obtained from crude oil and are economically
important?
I.
II.
III.
Plastics
Margarine
Motor fuel
A.
I and II only
B.
C.
D.
I, II and III
(Total 1 mark)
IB Questionbank Chemistry
38
62.
B.
C.
D.
63.
(a)
(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)
IB Questionbank Chemistry
39
(c)
Draw the three isomers containing the alcohol functional group of formula
C4H9OH.
(2)
(Total 5 marks)
IB Questionbank Chemistry
40
64.
The following is a computer-generated representation of the molecule, methyl 2hydroxy 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 carbonoxygen bond length in carbon dioxide.
(2)
(iii)
IB Questionbank Chemistry
41
65.
(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)
66.
(i)
Identify the formulas of the organic products, AE, formed in the reactions, IIV:
I.
H
CH3(CH2)8OH + K2Cr2O7 A
II.
(CH3)3CBr + NaOH C
III.
(CH3)2CHOH + K2Cr2O7
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)
IB Questionbank Chemistry
42