11 mark
Which of these organic compounds would undergo free radical substitution?
|
1 |
ethane |
|
2 |
fluoroethane |
|
3 |
ethene |
|
4 |
ethanal |
1 only
1 and 2
1, 2 and 3
All
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Syllabus Edition
First teaching 2014
Last exams 2024
|
Functional Group Chemistry (DP IB Chemistry: HL)
Exam Questions
3 hours51 questions
21 mark
Which of these compounds would act as a nucleophile?
C2H6
H+
OH-
Al
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31 mark
Which equation represents a correct propagation step in the free radical substitution reaction between ethane and chlorine?
C2H6 + Cl • → C2H5Cl + H•
C2H5• + Cl2 → C2H5Cl + Cl •
C2H6 + H• → C2H5• + HCl
C2H5• + Cl • → C2H5Cl
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41 mark
Ethene reacts with steam in the presence of sulfuric acid.
C2H4 + H2O → CH3CH2OH
What type of reaction is this?
acid / base
addition
hydrolysis
substitution
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51 mark
A molecule of a polymer contained the sequence shown.
Which monomer could produce this polymer by addition polymerisation?
CHCl =CHCl
CH2=CHCl
CH3CCl =CHCl
CH3CCl =CH2
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61 mark
The compound ‘leaf alcohol’ is partly responsible for the smell of new-mown grass.
CH3CH2CH=CHCH2CH2OH
leaf alcohol
What product will be formed when ‘leaf alcohol’ is oxidised using an excess of hot, acidified K2Cr2O7(aq)?
CH3CH2CH(OH)CH(OH)CH2CO2H
CH3CH2COCOCH2CO2H
CH3CH2CH=CHCH2CO2H
CH3CH2CO2H and HO2CCH2CO2H
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71 mark
Which of the alcohols shown below will decolourise acidified potassium manganate(VII)?
I.
CH3CH2CH2CH2OH
II.
CH3CH(OH)CH2CH3
III.
(CH3)3CCH2OH
I and II only
I and III only
II and III only
I, II and III
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81 mark
Ultraviolet light initiates the following reaction.
alkane + chlorine → chloroalkane + hydrogen chloride
What happens to chlorine in this photochemical reaction?
heterolytic fission to give an electrophile
homolytic fission to give an electrophile
heterolytic fission to give a positive and negative ion
homolytic fission to give free radicals
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91 mark
Which reaction is an example of nucleophilic substitution?
C6H6 + Br2 → C6H5Br+ HBr
CH2=CH2 + HBr → CH3CH2Br
C3H7Br + H2O → C3H7OH + HBr
C2H6 + Br2 → C2H5Br + HBr
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101 mark
Bromomethane, CH3Br, is used as a fumigant to destroy insect pests in grain that is to be stored. It can be made by reacting methanol with hydrogen bromide.
CH3OH + HBr → CH3Br + H2O
What type of reaction is this?
condensation
electrophilic substitution
free radical substitution
nucleophilic substitution
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111 mark
What reagents and conditions are needed to convert but-2-ene into butane?
Concentrated sulfuric acid, steam, 300oC
Hydrogen gas, Ni catalyst, 150oC
Acidified potassium dichromate, heating under reflux
Hydrogen bromide, room temperature
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121 mark
Which of the following products are possible from the incomplete combustion of alkanes?
I.
C
II. CO
III.
H2
I and II only
I and III only
II and III only
I, II and III
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131 mark
What can be produced when an aqueous solution of butan-2-ol is oxidised under suitable conditions?
|
1 |
butanone |
|
2 |
butanoic acid |
|
3 |
butanal |
1, 2 and 3
1 and 2 only
2 and 3 only
1 only
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141 mark
The ester in the diagram below has an odour of banana.
Which pair of reactants can be used to produce this ester under suitable conditions?
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11 mark
Xylitol is an artificial sweetener used in toothpastes and chewing gum to improve their taste without impairing dental hygiene.
Which functional groups could be produced if Xylitol is oxidised under suitable conditions?
|
1 |
alkene |
|
2 |
aldehyde |
|
3 |
carboxylic acid |
|
4 |
ketone |
1 only
2 only
2, 3 and 4
2 and 4
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21 mark
Isomers X and Y both react with HBr.
A mixture of X and Y is reacted with HBr.
Which three structures represent three different possible products of this reaction?
|
A |
(CH3)2CHCBr3 |
(CH3)2CBrCHBr2 |
CH3CHBrCHBrCH3 |
|
B |
(CH3)2CHCBr3 |
(CH3)2CBrCHBr2 |
CH3CBr2CHBrCH3 |
|
C |
(CH3)2CBrCBr3 |
(CH3)2CHCBr3 |
CH3CBr2CHBrCH3 |
|
D |
(CH3)2CBrCHBr2 |
CHBr2CBr(CH3)CH3 |
CH3CHBrCBr2CH3 |
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31 mark
In the presence of ultraviolet light, ethane and chlorine react to give a mixture of products.
Which compound could be present in the mixture of products?
CH3Cl
CH3CH2CH2Cl
CH3CH2CH2CH3
CH3CH2CH2CH2CH3
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41 mark
Dichlorodifluoromethane, CCl2F2, has been used in aerosol propellants and as a refrigerant.
Which statement helps to explain why dichlorodifluoromethane is chemically inert?
the carbon-fluorine bond energy is large
the carbon-fluorine bond has a low polarity
fluorine is highly electronegative
fluorine compounds are non-flammable
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51 mark
In the hydrolysis of bromoethane by aqueous sodium hydroxide, what is the nature of the attacking group and of the leaving group?
|
|
attacking group |
leaving group |
|
A B C D |
electrophile electrophile nucleophile nucleophile |
electrophile nucleophile electrophile nucleophile |
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61 mark
Which volume of oxygen measured at room temperature and pressure is needed for complete combustion of 0.1 mol of propane? (Molar volume = 24dm3 at rtp)
12.0 dm3
5.0 dm3
20.0 dm3
24.0 dm3
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71 mark
2.30 g of ethanol were mixed with aqueous acidified potassium dichromate(VI) and the desired organic product was collected by immediate distillation under gentle warming. The yield of the product was 50.0%. ( RAMs C= 12, H=1, O=16)
What mass of product was collected?
1.10 g
1.15 g
2.20 g
2.30 g
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81 mark
Which alcohol gives only one possible oxidation product when warmed with dilute acidified potassium dichromate(VI)?
butan-1-ol
butan-2-ol
2-methylpropan-1-ol
2-methylpropan-2-ol
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91 mark
Hydroxyethanal has the structural formula HOCH2CHO.
In an experiment hydroxyethanal is heated under reflux with an excess of acidified potassium dichromate(VI) until no further oxidation takes place.
What is the skeletal formula of the organic product formed in the experiment?
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101 mark
The diagram shows the structure of ethanedioic acid.
Ethanedioic acid reacts with ethanol in the presence of a few drops of concentrated sulfuric acid to form a diester. The molecular formula of the diester is C6H10O4.
What is the structural formula of the diester?
CH3CH2CO2CO2CH2CH3
CH3CH2OCOCO2CH2CH3
CH3CH2O2CO2CCH2CH3
CH3CO2CH2CH2OCOCH3
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111 mark
Compound Q has the formula CH3CH2CO2CH3
What is the name of compound Q and how does its boiling point compare with that of butanoic acid?
|
|
name of Q |
boiling point compared to butanoic acid |
|
A B C D |
methyl propanoate propyl methanoate methyl propanoate propyl methanoate |
lower lower higher higher |
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121 mark
How many ester compounds have the molecular formula C4H8O2?
2
3
4
5
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11 mark
Limonene is an oil formed in the peel of citrus fruits.
Which product is formed when an excess of bromine, Br2(l), reacts with limonene at room temperature in the dark?
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21 mark
Samples of 10 cm3 of each of the first four members of the alkane series are separately mixed with 70 cm3 of oxygen. Each is then burned and the total volume, V, of residual gas measured again at room temperature and pressure.
Which graph represents the results that would be obtained?
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31 mark
A periodic table is needed for this question
Which compound has an Mr of 84.18 and will react with HBr to give a product with an Mr of 165.09?
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41 mark
An organic compound Y with molecular formula C5H12O, is oxidised to compound Z with molecular formula C5H10O2.
What could be the structural formula of Y?
|
1 |
CH3(CH2)4OH |
|
2 |
CH3CH2CH(CH2OH)CH3 |
|
3 |
CH3C(CH3)2CH2OH |
1, 2 and 3
1 and 3 only
2 and 3 only
3 only
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51 mark
A periodic table is needed to answer this question
A number of alcohols with the formula C4H10O are separately oxidised. Using 7.41 g of the alcohols a 50% yield of organic product is achieved.
What mass of product could be obtained?
|
1 |
4.41 g of butanoic acid |
|
2 |
4.41 g of 2-methylpropanoic acid |
|
3 |
3.61 g of butanone |
1, 2 and 3
1 and 2 only
2 and 3 only
1 only
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61 mark
Which compound is produced in the reaction between pent-2-ene and steam?
(CH3)2CHCH2CH2OH
CH3CH(OH)CH2CH2CH2CH3
CH3CH2CH2CH2CH2OH
CH3CH2CH2CH(OH)CH3
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71 mark
When compound T reacts with its own oxidation product, a sweet-smelling liquid is produced.
What is the identity of compound T?
butanal
butanone
butan-1-ol
butanoic acid
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81 mark
In the presence of an H+ catalyst, compound X reacts with ethanoic acid to produce the compound below.
What is the molecular formula of compound X?
C4H8O
C4H8O2
C2H6O2
C2H6O3
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91 mark
Compound K, C5H12O, is oxidised by acidified sodium dichromate(VI) to compound L.
Compound L reacts with butan-2-ol in the presence of a little concentrated sulfuric acid to give liquid M.
What could be the formula of liquid M?
(CH3)2CHCH2CO2C(CH3)3
CH3(CH2)3CO2(CH2)3CH3
CH3(CH2)3CO2CH(CH3)CH2CH3
CH3(CH2)2CO2CH2CH2(CH3)2
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101 mark
Shown below is a reaction sequence starting with 1-chlorobutane.
I II III
C4H9Cl → C4H9OH → C3H7COOH → C3H7COOC3H7
What is the correct classification of the types of reactions shown?
|
|
I |
II |
III |
|
A |
substitution |
oxidation |
substitution |
|
B |
addition |
substitution |
condensation |
|
C |
oxidation |
substitution |
condensation |
|
D |
substitution |
oxidation |
condensation |
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