Syllabus Edition
First teaching 2023
First exams 2025
Which of the following shows the correct order of boiling points for pentane, butane and propane?
CH3CH2CH3 > CH3CH2CH2CH3 > CH3CH2CH2CH2CH3
CH3CH2CH2CH2CH3 > CH3CH2CH2CH3 > CH3CH2CH3
CH3CH2CH2CH3 > CH3CH2CH2CH2CH3 > CH3CH2CH3
CH3CH2CH3 > CH3CH2CH2CH2CH3 > CH3CH2CH2CH3
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Which of the following statements about propanal, CH3CH2CHO, and propanone, CH3COCH3 is not correct?
The compounds have:
molecular ion peaks at different mass to charge ratios
different fragmentation patterns in the mass spectrum
absorption in the infrared spectrum due to the carbonyl group
a different fingerprint region in the infrared spectrum
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Nitrogen trichloride has the formula NCl3. A sample was found to contain only 14N, and chlorine atoms with mass numbers 35 and 37.
Which of the following is an incorrect ion and mass/charge ratio responsible for the molecular ion peaks found in the mass spectrum of nitrogen trichloride?
|
|
ion |
m/e |
|
A |
N(35Cl)3+ |
119 |
|
B |
N(35Cl)237Cl+ |
121 |
|
C |
N35Cl(37Cl)2+ |
123 |
|
D |
N(37Cl)2+ |
125 |
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Which of the following cannot be obtained from an infrared spectrum?
the molecular mass
the presence of C=O bonds
the presence of O-H bonds
the identity of a compound through comparison with other spectra
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What information can be determined from the infrared spectrum of a molecule?
The number of hydrogens
The number of hydrogen environments
The type of bonds present
The relative molecular mass
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Which of the following bonds will produce strong absorptions in the infrared part of the electromagnetic spectrum?
I and II only
I and III only
II and III only
I, II and III
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Which of the following is true about the fingerprint region in the IR spectrum of alcohols?
The fingerprint region is where single bonds can be identified in the IR spectrum
The fingerprint region is unique to every molecule
The fingerprint region does not provide useful information about molecules
A functional group can be identified from the fingerprint region
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Which of the following statements is correct about spectroscopic techniques for organic molecules?
Information about bond vibrations can be deduced from mass spectroscopy
The values of carbon–hydrogen bond lengths can be found from 1H NMR spectroscopy
The number of hydrogen atoms can be determined from infrared spectroscopy
Information about molecular structure can be found from mass spectroscopy
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In the 1H NMR spectrum of 3-methylbutan-1-ol what is the ratio of the peak areas under each signal?
6 : 1 : 2 : 2 : 1
3 : 3 : 1 : 5 : 1
6 : 1 : 5 : 1
3 : 3 : 1 : 2 : 3
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Which of the following types of spectroscopic identification will involve bond fission in organic molecules?
Nuclear magnetic spectroscopy
Infrared spectroscopy
Mass spectrometry
X-ray crystallography
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Which pairs of homologous series do not have the same C:H ratio in their general formulae?
aldehydes and ketones
alkanes and alkenes
carboxylic acids and esters
alkenes and aldehydes
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Which of the following molecules are hydrocarbons?
All
1 and 2
1, 2 and 3
2, 3 and 4
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What is the correct formula for 1-fluoro-3-methylbut-2-ene?
|
A |
Molecular |
CH2FCH2C(CH3)CH3 |
|
B |
Empirical |
C5H9F |
|
C |
Displayed |
 |
|
D |
Skeletal |
|
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Considering only structural isomers, what is the number of alcohols of each type with the formula C5H12O?
|
primary |
secondary |
tertiary |
|
|
A B C D |
3 4 4 5 |
3 2 3 2 |
2 2 1 1 |
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Which of the following is the displayed formula for ethylamine?
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Identify which of the hydrocarbons shown below does not belong in the same homologous series as the other compounds
C5H12
C6H12
C7H16
C8H18
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Identify the functional group that is ringed in the molecule shown below:
hydroxyl
carboxyl
ether
carbonyl
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What is the IUPAC name of the following molecule?
2-chloro-3-ethylbutane
3-methyl-4-chloropentane
2-ethyl-3-chlorobutane
2-chloro-3-methylpentane
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What is the IUPAC name of the following molecule?
3,3-dimethylpropanoic acid
1,1-dimethylpropanoic acid
3-methylbutanoic acid
2-methylbutanoic acid
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Which of the halogenoalkanes shown contains a secondary carbon atom?
(CH3)2CHCH2Cl
CH3(CH2)3CH2Cl
(CH3)3CCl
CH3CHClCH2CH3
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1 markWhich molecule contains a chiral carbon?
1-chloro-2-methylbutane
2-methylpropane
Butane
2-chloropropane
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1 markWhat is name of this compound applying IUPAC rules?
Trans-pent-2-ene
Trans-but-2-ene
But-1-ene
Cis-but-2-ene
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1 markWhich statement about isomerism is correct?
A racemic mixture is optically active
Pent-1-ene exhibits stereoisomerism
1-bromopropane has two optical isomers
2-amino-3-methylpentane is a diastereomer
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1 markWhich pair are cis and trans isomers?
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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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Which alcohol is not likely to have a fragment at m/e at 43 in its mass spectrum?
(CH3)2CHCH2OH
CH3CH(OH)CH2CH2CH3
CH3CH2CH2CH2OH
CH3CH2CH(OH)CH3
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Which of the compounds shown below is likely to have a fragment at m/e = 45 in its mass spectrum?
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Chlorine has two isotopes 35Cl and 37Cl. Assuming in the molecule C4H6Cl4 there is only one hydrogen and one carbon isotope, how many molecular ion peaks will be seen in its mass spectrum?
5
4
3
2
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Bromine exists as two isotopes 79Br and 81Br, which are found in almost equal abundance.
Which of the following statements is correct?
79Br is more reactive than 81Br
The mass spectrum of C3H7Br has two molecular ion peaks at 122 and 124
The atomic radius of 79Br is less than the atomic radius of 81Br
The first ionisation energy of 79Br is less than the first ionisation energy of 81Br
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Which alcohol is likely to have a fragment ion at m/e = 31 in its mass spectrum?
CH3)2CHCH2OH
CH3CH(OH)CH2CH2CH3
CH3CH2CH2C(OH)(CH3)2
CH3CH2CH(OH)CH3
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Which pair of compounds would you expect to both have a singly charged peak at m/e = 29 in the mass spectrum?
propan-1-ol and propanal
propanal and propanone
propan-2-ol and propanal
propan-1-ol and propan-2-ol
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The infrared spectrum of a compound is shown below.
Use the infrared absorptions, in wavenumbers, to identify the compound
|
bond |
wavenumber range/ cm-1 |
|
O−H (alcohol) |
3750 – 3200 |
|
C−H (alkane) |
2962 – 2853 |
|
C−H (aldehyde) |
2900 – 2820 and 2775 – 2700 |
|
C═O (aldehyde or ketone) |
1740 - 1680 |
Which compound is shown by the infrared spectrum?
propan-1-ol
propan-2-ol
propanal
propanone
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Which of the ketones listed would not be expected to have a peak in its mass spectrum at m/e = 57?
hexan-3-one, CH3CH2CH2COCH2CH3
pentan-3-one, CH3CH2COCH2CH3
3-methylbutanone, (CH3)2CHCOCH3
butanone, CH3CH2COCH3
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Which of the following statements about the mass spectrum of CH3Br is correct?
There is one peak for the molecular ion with an m/e value of 44.
There is one peak for the molecular ion with an m/e value of 95.
The last two peaks have abundances in the ratio 3:1 and occur at m/e values of 94 and 96.
The last two peaks are of equal size and occur at m/e values of 94 and 96.
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Below is a 1H NMR spectrum for an unknown organic compound. The relative areas under the peaks are labelled
Which of the following compounds could give this spectrum?
propan-1-ol, CH3CH2CH2OH
propan-2-ol, CH3CH(OH)CH3
methyoxyethane, CH3OCH2CH3
pentan-2-one, CH3CH2CH2COCH3
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How many structural isomers are there of tribromopropane, C3H5Br3?
4
5
6
7
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How many isomeric esters have the molecular formula C5H10O2?
4
5
9
7
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Which features about the members of a homologous series are correct?
I and II only
I and III only
II and III only
I, II and III
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Octane is a component of petrol or gasoline. Which of the following molecules could be an isomer of octane?
CH3CH2CHCHCHCH2(CH3)2
(CH3)2CHCH(CH2)2(CH3)2
CH3(CH2)5CH3
CH3CHCHCH(CH2)2(CH3)2
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Give the name of the following molecule
2,4,4,4-trimethylethylbutane
3,3,5-trimethylhexane
2,4,4-trimethylhexane
1,1,3,3-tetramethylpentane
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How many branched-chain isomers are there which have the molecular formula C5H12?
2
3
4
5
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Study the diagram below and determine which of the three statements are correct
I and II only
I and III only
II and III only
I, II and III
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Which of the molecules shown below contains an aldehyde functional group?
CH3CH2CH2OOCH3
CH3CH2CH2COCH3
CH3CH2OCH2CH3
CH3CH2CH2CH2CHO
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Which of the halogenoalkanes shown below contains a tertiary carbon atom?
CH3CH2CH2Cl
CH3CH2CH(CH3)Br
C(CH3)3Cl
CH3CHBrCH2CH3
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What would be the name of the following compound using IUPAC rules?
pentane
ethylpropane
2-methylbutane
3-methylbutane
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Which two molecules are cis-trans isomers of each other?
X and Z
X and Y
W and Y
W and Z
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What is this molecule called?
Z-2-bromo-1-chloro-2-fluoroethene
E-2-bromo-1-chloro-2-fluoroethene
Z-1-bromo-2-chloro-1-fluoroethene
E-1-bromo-2-chloro-1-fluoroethene
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Which molecule has optical isomers?
2-bromobutane
1,3-dibromopropane
2-chloro-2-methylpropane
3-bromopentane
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What is the name of this molecule?
cis-3-methyl-3-hexene
trans-4-methyl-4-hexene
cis-3-methyl-2-hexene
trans-3-methyl-2-hexene
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Which is true about stereoisomerism?
But-1-ene has E/Z isomers
Butan-2-ol has two enantiomers
But-1-ene and but-2-ene are cis-trans isomers
Butan-1-ol and butan-2-ol are optical isomers
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The mass spectra of three compounds A, B and C are shown below.
What evidence from the spectra of the three compounds A, B and C, suggests they could be isomers?
all show a molecular ion peak at 74
all show a molecular ion peak at 13
all show a molecular ion peak at 73
all show a molecular ion peak at 33
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The infrared spectrum below shows an unknown compound.
|
bond |
wavenumber range/ cm-1 |
|
C−O; hydroxyl, ester |
1040 – 1300 |
|
C═C; aromatic compound, alkene |
1500 - 1680 |
|
C═O amide carbonyl, carboxyl ester |
1640 – 1690 1670 – 1740 1710 - 1750 |
|
C≡N; nitrile |
2200 – 2250 |
|
C−H; alkane |
2850 – 2950 |
|
N−H; amine, amide |
3300 – 3500 |
|
O−H; carboxyl hydroxyl |
2500 – 3000 3200 - 3600 |
Which compound could have produced the infrared spectrum?
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The diagram shows an infrared spectrum of a compound.
|
bond |
wavenumber range/ cm-1 |
|
C−O; hydroxyl, ester |
1040 – 1300 |
|
C═C; aromatic compound, alkene |
1500 - 1680 |
|
C═O amide carbonyl, carboxyl ester |
1640 – 1690 1670 – 1740 1710 - 1750 |
|
C≡N; nitrile |
2200 – 2250 |
|
C−H; alkane |
2850 – 2950 |
|
N−H; amine, amide |
3300 – 3500 |
|
O−H; carboxyl hydroxyl |
2500 – 3000 3200 - 3600 |
Which compound would give this spectrum?
butanoic acid
butanal
butan-1-ol
1-bromobutane
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Which of the following infrared spectra could show a carboxylic acid?
|
Bond |
Wavenumber range/ cm-1 |
|
C−O; hydroxyl, ester |
1040 – 1300 |
|
C═C; aromatic compound, alkene |
1500 - 1680 |
|
C═O amide carbonyl, carboxyl ester |
1640 – 1690 1670 – 1740 1710 - 1750 |
|
C≡N; nitrile |
2200 – 2250 |
|
C−H; alkane |
2850 – 2950 |
|
N−H; amine, amide |
3300 – 3500 |
|
O−H; carboxyl hydroxyl |
2500 – 3000 3200 - 3600 |
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A compound XFn is a fluoride of another halogen, X, and it is known that n > 1. The highest m/e peak in the mass spectrum of XFn is assigned to the parent ion and comes as a single peak at m/e = 222.
Which of the following statements is incorrect?
n = 5
the compound could contain bromine
there are no isotopes of X or F
the compound is a fluoride of iodine
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An organic compound is analysed by mass spectrometry and infrared spectroscopy. The following data is obtained.
|
mass spectrometry |
infrared spectroscopy |
|
molecular ion peak at m/e = 128 |
sharp peak at 1720 cm-1 |
|
fragment ion peak at m/e = 15 |
no broad peak around 3200 cm-1 |
|
Bond |
Wavenumber range/ cm-1 |
|
C−O; hydroxyl, ester |
1040 – 1300 |
|
C═C; aromatic compound, alkene |
1500 - 1680 |
|
C═O amide carbonyl, carboxyl ester |
1640 – 1690 1670 – 1740 1710 - 1750 |
|
C≡N; nitrile |
2200 – 2250 |
|
C−H; alkane |
2850 – 2950 |
|
N−H; amine, amide |
3300 – 3500 |
|
O−H; carboxyl hydroxyl |
2500 – 3000 3200 - 3600 |
Which of the following compounds could be consistent with the data given?
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What does the 1H NMR spectrum below tell you about a molecule?
There is only one isotope of hydrogen present in the molecule
The molecule is a hydrocarbon
There is only one hydrogen atom in the molecule
There is only one hydrogen environment in the molecule
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How many peaks would you expect to see in a 1H NMR spectrum of methylbenzene?
3
4
5
6
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How many isomers, including structural and stereoisomers, with the formula C5H10 have structures that involve π bonding?
3
4
5
6
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Study the formulae shown below and determine which molecules are isomers of each other
I and II only
I and III only
II and III only
I, II and III
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What is the correct condensed structural formula for 2,2-dibromo-4-methylhexane?
CH3CBr2CH(CH3)CH2CH2CH3
CH3CHBrCBr(CH3)CH2CH2CH3
CH3CBr2CH2CH(CH3)CH2CH3
CH3CHBrCH(CH3)CHBrCH2CH3
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What is the correct IUPAC name for the molecule shown?
ethoxyethane
methoxyethane
propanone
propanal
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Which of the molecules shown below is not an isomer of pentan-2-ol?
pentan-1-ol
2-methylbutan-2-ol
2-methylpentan-2-ol
pentan-3-ol
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Which of the following pairs are functional group isomers?
I and II only
I and III only
II and III only
I, II and III
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What is the correct name of the following molecule using IUPAC rules?
propyl methanoate
methyl propanoate
methoxypropane
butoxymethanal
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What types of isomerism can the following molecule show?
I and II only
I and III only
II and III only
I, II and III
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1 markHow many dimethyl cyclopentane isomers are disubstituted and have the cyclopentane structure?
3
4
5
6
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1 markWhich structure is the correct cis trans isomer of trans-1,2-dibromocyclobutane?
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1 markWhich molecule has a chiral centre?
CH3OCH2CH3
CH3CH2CHO
CH3CH(NH2)CH3
CH3CH(OH)CH2CH3
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1 markArthrinin-F is a compound isolated from fungus.
What is the correct number of chiral carbons in the structure?
2
3
4
5
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