Topic 10 Paper 1 [70 marks]

1. [1 mark]
Which are isomers of C5H12?

A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
A
2. [1 mark]
Which homologous series has the general formula CnH2nO (n > 2)?

A. Alcohols
B. Carboxylic acids
C. Ethers
D. Ketones

Markscheme
D
3. [1 mark]
Which conditions best favour oxidation of primary alcohols directly to carboxylic acids?
A. Excess acidified potassium dichromate (VI) and distillation
B. Excess acidified potassium dichromate (VI) and reflux
C. Few drops of acidified potassium dichromate (VI) and distillation
D. Few drops of acidified potassium dichromate (VI) and reflux

Markscheme
B
4. [1 mark]
What are nucleophiles most likely to react with?

A. Alkenes
B. Benzene
C. Alkanes
D. Halogenoalkanes

Markscheme
D
5. [1 mark]
What information about 2-hydroxybutanoic acid can be inferred through mass
spectrometry, MS, infrared spectroscopy, IR, and proton nuclear magnetic resonance
spectroscopy, 1H NMR?
Markscheme
A
6. [1 mark]
Which functional groups are present in serine?

A. nitro, carbonyl and carboxyl

B. amino, hydroxyl and carbonyl
C. nitro, carboxyl and hydroxyl
D. amino, carboxyl and hydroxyl

Markscheme
D
7. [1 mark]
Which compounds are members of the same homologous series?
A. propanal, propanone, propanoic acid
B. propane, propene, propyne
C. hexan-1-ol, hexan-2-ol, hexan-3-ol
D. ethanol, propan-1-ol, butan-1-ol

Markscheme
D
8. [1 mark]
Which reagents and conditions are best for converting propan-1-ol into propanoic acid?
A. Reflux with acidified potassium dichromate (VI)
B. Reflux with aqueous sodium hydroxide
C. Distil with acidified potassium dichromate (VI)
D. Distil with aqueous sodium hydroxide
Markscheme
A
9. [1 mark]
What is produced when chlorobutane is treated with aqueous sodium hydroxide solution?
A. butane
B. butanoic acid
C. butanal
D. butan-1-ol

Markscheme
D
10. [1 mark]
Which combination best describes what is happening to chloromethane, CH 3Cl, in the
equation below?
CH3Cl (g) + H2 (g) ⇌ CH4 (g) + HCl (g)
A. Oxidation and addition
B. Oxidation and substitution
C. Reduction and addition
D. Reduction and substitution

Markscheme
D
11. [1 mark]
How many dichlorinated butane isomers can be formed by the halogenation of
CH3CH2CH2CH3 with excess Cl2 in the presence of UV light?
A. 4
B. 6
C. 8
D. 10
Markscheme
B
12. [1 mark]
Which structure represents 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–

Markscheme
A
13. [1 mark]
Which is a homologous series?
A. C2H4, C3H5, C4H6
B. C2H2, C3H4, C4H6
C. C2H2, C2H4, C2H6
D. C2H2, C4H4, C6H6

Markscheme
B
14. [1 mark]
Which reaction mechanisms are typical for alcohols and halogenoalkanes?
Markscheme
D
15. [1 mark]
What is the name of this substance using IUPAC rules?

A. 2-ethyl-1-methylbutan-1-ol
B. 1-methyl-2-ethylbutan-1-ol
C. 3-ethylpentan-2-ol
D. 3-ethylpentan-4-ol

Markscheme
C
16. [1 mark]
Which pair of compounds are structural isomers?
A. Propane and propene
B. Propanal and propanone
C. Propan-1-ol and propanal
D. Propyl propanoate and propanoic acid

Markscheme
B
17. [1 mark]
What is the general formula of alkynes?

A. CnH2n+2
B. CnH2n
C. CnH2n−2
D. CnHn

Markscheme
C
18. [1 mark]
Which series is in order of increasing boiling point?
A. CH2CH2CH3OH CH3COCH3 CH3CH2CH3
B. CH3CH2CH3 CH3COCH3 CH2CH2CH3OH
C. CH3COCH3 CH2CH2CH3OH CH3CH2CH3
D. CH3CH2CH3 CH2CH2CH3OH CH3COCH3

Markscheme
B
19. [1 mark]
What is the name of this compound, applying IUPAC rules?
A. 4-methylhex-2-ene
B. 4-ethylpent-2-ene
C. 2-ethylpent-3-ene
D. 3-methylhex-4-ene

Markscheme
A
20. [1 mark]
What is formed in a propagation step of the substitution reaction between bromine and
ethane?
A. CH3CH2•
B. CH3CH2CH2CH3
C. H•
D. Br−

Markscheme
A
21. [1 mark]
Which monomer would produce the polymer shown?
A. CF 3 CCl2 F

B. CF 3 CClHF

C. CF 2 CClF

D. CF 2 CF 2

Markscheme
C
22. [1 mark]
Which is in the same homologous series as CH3OCH3?
A. CH3COCH3
B. CH3COOCH3
C. CH3CH2CH2OH
D. CH3CH2CH2OCH3

Markscheme
D
23. [1 mark]
What is the IUPAC name of the molecule shown?

A. 2,4-dimethylhexane
B. 3,5-dimethylhexane
C. 2-methyl-4-ethylpentane
D. 2-ethyl-4-methylpentane

Markscheme
A
24. [1 mark]
Which monomer forms the polymer shown?
A. CH (Cl)=CH (CH ¿¿ 3)¿
B. CH 2 ¿ C (Cl)CH 3
C. ¿ ¿
D. CH 2=CHCl

Markscheme
A
25. [1 mark]
Which is a propagation step in the free-radical substitution mechanism of ethane with
chlorine?
A. Cl 2 → 2 •Cl
B. •C2H5 + Cl 2 → C2H5Cl + •Cl
C. •C2H5 + •Cl → C2H5Cl
D. C2H6 + •Cl → C2H5Cl + •H

Markscheme
B
26. [1 mark]
Which spectra would show the difference between propan-2-ol, CH 3CH(OH)CH3, and
propanal, CH3CH2CHO?
I. mass
II. infrared
III. 1H NMR
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
D
27. [1 mark]
Which functional groups are present in this molecule?

A. carbonyl, ether, nitrile

B. carbonyl, ester, nitrile

C. carboxyl, ether, amine

D. carboxyl, ester, amine

Markscheme
A
28. [1 mark]
Which molecule will decolorize bromine water in the dark?
A. cyclohexane

B. hexane
C. hex-1-ene

D. hexan-1-ol

Markscheme
C
29. [1 mark]
What is the IUPAC name of this molecule?

A. 1,1,2,4-tetramethylpent-1-ene

B. 2,4,5-trimethylhex-4-ene

C. 2,4,5,5-tetramethylpent-4-ene

D. 2,3,5-trimethylhex-2-ene

Markscheme
D
30. [1 mark]
Which mechanism does benzene most readily undergo?
A. Nucleophilic substitution

B. Electrophilic substitution

C. Electrophilic addition

D. Free radical substitution

Markscheme
B
31. [1 mark]
Which compound is not in the same homologous series as the others?
A. C5H12
B. C6H12

C. C7H16

D. C8H18

Markscheme
B
32. [1 mark]
What type of reaction occurs when C6H13Br becomes C6H13OH?

A. Nucleophilic substitution

B. Electrophilic substitution

C. Radical substitution

D. Addition

Markscheme
A
33. [1 mark]
Which will react with a halogen by an electrophilic substitution mechanism?
Markscheme
A
34. [1 mark]
Which compound cannot undergo addition polymerization?

Markscheme
C
35. [1 mark]
Which functional group is surrounded in the molecule?

A. hydroxyl
B. carboxyl
C. carbonyl
D. ether

Markscheme
C
36. [1 mark]
What is the IUPAC name of the following molecule?

A. 2-bromo-3-ethylbutane
B. 3-methyl-4-bromopentane
C. 2-ethyl-3-bromobutane
D. 2-bromo-3-methylpentane

Markscheme
D
37. [1 mark]
What is the mechanism of the reaction between alkenes and halogens in the absence of
light?
A. radical substitution
B. electrophilic substitution
C. electrophilic addition
D. nucleophilic substitution

Markscheme
C
38. [1 mark]
Which alcohol would produce a carboxylic acid when heated with acidified potassium
dichromate(VI)?
A. propan-2-ol
B. butan-1-ol
C. 2-methylpropan-2-ol
D. pentan-3-ol

Markscheme
B
39. [1 mark]
Which compound has the lowest boiling point?
A. CH3CH2CH2CH2CH2CH3
B. CH3CH2CH2CH2CH3
C. CH3CH(CH3)CH2CH3
D. CH3C(CH3)2CH3

Markscheme
D
40. [1 mark]
Which of the following can be both formed from bromoethane and converted directly into
ethanal?
CH3CH2Br → X
X → CH3CHO
A. CH3CH2OH
B. CH3OCH3
C. CH3COOH
D. H2C=CHBr

Markscheme
A
41. [1 mark]
Methane reacts with chlorine in sunlight.
CH4 (g) + Cl2 (g) → CH3Cl (g) + HCl (g)
Which type of reaction occurs?
A. free-radical substitution
B. electrophilic substitution
C. nucleophilic substitution
D. electrophilic addition

Markscheme
A
42. [1 mark]
Which compounds cause the colour of acidified potassium manganate(VII) solution to
change from purple to colourless?
I. CH3CH2CH2CH2OH
II. (CH3)3CCH2OH
III. CH3CH2CH(OH)CH3

A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
D
43. [1 mark]
What is the order of increasing boiling point for the isomers of C 5H12?

A. CH3CH2CH2CH2CH3 < CH3CH(CH3)CH2CH3 < CH3C(CH3)3

B. CH3C(CH3)3 < CH3CH(CH3)CH2CH3 < CH3CH2CH2CH2CH3
C. CH3C(CH3)3 < CH3CH2CH2CH2CH3 < CH3CH(CH3)CH2CH3
D. CH3CH(CH3)CH2CH3 < CH3C(CH3)3 < CH3CH2CH2CH2CH3
Markscheme
B
44. [1 mark]
Which is correct for benzene?

A. It readily undergoes addition reactions and decolourises bromine water.

B. It contains alternate single and double carbon–carbon bonds and is planar.
C. Its 1H NMR spectrum shows six signals and it readily undergoes substitution reactions.
D. Its 1H NMR spectrum shows one signal and it forms a single C6H5Br isomer.

Markscheme
D
45. [1 mark]
Which compounds react to form CH3CH2CH2COOCH(CH3)2?

A. propanoic acid and propan-2-ol

B. propanoic acid and butan-2-ol
C. butanoic acid and propan-1-ol
D. butanoic acid and propan-2-ol

Markscheme
D
46. [1 mark]
What are possible names of a molecule with molecular formula C4H10O?
I. 1-Methoxypropane
II. 2-Methylpropan-2-ol
III. Butanal
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
A
47. [1 mark]
What is the product of the reaction between hex-3-ene and steam?
A. Hexan-1-ol
B. Hexan-2-ol
C. Hexan-3-ol
D. Hexan-4-ol

Markscheme
C
48. [1 mark]
Which of these reactions proceeds by a free radical mechanism in the presence of UV light?
A. C6H6 + Cl2 → C6H5Cl + HCl
B. C6H6 + 3H2 → C6H12
C. CH2CH2 + HBr → CH3CH2Br
D. CH3CH3 + Cl2 → CH3CH2Cl + HCl

Markscheme
D
49. [1 mark]
Which compound could be formed when CH3CH2CH2OH is heated with acidified potassium
dichromate(VI)?
I. CH3CH2CHO
II. CH3CH2COOH
III. CH3COCH3
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
A
50. [1 mark]
Which compounds belong to the same homologous series?
A. CHCCH2CH3, CHCCH2CH2CH3
B. CH3CH2CH2CH2OH, CH3CH2OCH2CH3
C. CH2CHCH3, CH3CH2CH2CH3
D. CH3COCH3, CH3CH2OCH3

Markscheme
A
51. [1 mark]
What is the name of this compound, using IUPAC rules?

A. 1,1-dimethylpropanoic acid
B. 3,3-dimethylpropanoic acid
C. 2-methylbutanoic acid
D. 3-methylbutanoic acid

Markscheme
D
52. [1 mark]
What is the mechanism for the reaction of propene with iodine in the dark?
A. electrophilic addition
B. electrophilic substitution
C. free radical substitution
D. nucleophilic substitution

Markscheme
A
53. [1 mark]
Which are structural isomers?
I. CH3CH2OH and CH3OCH3
II. HOCH2CH3 and CH3CH2OH
III. CH3COOH and HCOOCH3
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
B
54. [1 mark]
What is the major product of the reaction between HCl and but-2-ene?
A. 1,2-dichlorobutane
B. 2,3-dichlorobutane
C. 1-chlorobutane
D. 2-chlorobutane

Markscheme
D
55. [1 mark]
Which compound can be oxidized when heated with an acidified solution of
potassium dichromate(VI)?
A. CH3C(O)CH2CH3
B. CH3CH2CH(OH)CH3
C. (CH3)3COH
D. CH3(CH2)2COOH

Markscheme
B
56. [1 mark]
What is the name of this compound, using IUPAC rules?

A. 3-methylbutan-3-ol
B. 2-ethylpropan-2-ol
C. 2-methylbutan-2-ol
D. 3-methylbutan-2-ol

Markscheme
C
57. [1 mark]
Which type of reaction occurs between an alcohol and a carboxylic acid?
A. Addition
B. Oxidation
C. Esterification
D. Polymerization

Markscheme
C
58. [1 mark]
How many structural isomers of C6H14 exist?
A. 4
B. 5
C. 6
D. 7

Markscheme
B
59. [1 mark]
What is the order of increasing boiling point?
A. C4H10 < CH3COOH < CH3CH2CHO < CH3CH2CH2OH
B. C4H10 < CH3CH2CHO < CH3CH2CH2OH < CH3COOH
C. CH3COOH < CH3CH2CH2OH< CH3CH2CHO < C4H10
D. C4H10 < CH3CH2CH2OH < CH3CH2CHO < CH3COOH

Markscheme
B
60. [1 mark]
What are the functional groups in the aspirin molecule?
 I. Ether
II . Carboxyl
III . Ester
¿
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
C
61. [1 mark]
What is the name of the compound with this molecular structure applying IUPAC rules?
A. 1-methylpropanoic acid
B. 2-methylpropanoic acid
C. 2-methylbutanoic acid
D. 3-methylbutanoic acid

Markscheme
C
62. [1 mark]
Which molecule has a tertiary nitrogen?
A. (CH3)2NH
B. (C2H5)4N+I−
C. C3H7N(CH3)2
D. C6H5NH2

Markscheme
C
63. [1 mark]
Which functional group is present in paracetamol?
A. Carboxyl
B. Amino
C. Nitrile
D. Hydroxyl

Markscheme
D
64. [1 mark]
Which describes the reaction between a halogen and ethane?
Markscheme
A
65. [1 mark]
Which conditions are used to convert ethanol to ethanal?
A. Excess oxidizing agent and reflux
B. Excess oxidizing agent and distillation
C. Excess ethanol and reflux
D. Excess ethanol and distillation

Markscheme
D
66. [1 mark]
Which compound contains a secondary carbon atom?
A. CH3CH(Cl)CH(CH3)2
B. (CH3)2CHCH2Cl
C. (CH3)3CCl
D. CH3CH2Cl

Markscheme
A
67. [1 mark]
The structure of a drug used to treat symptoms of Alzheimer’s disease is shown below.
Which functional groups are present in this molecule?
A. Hydroxyl and ester
B. Hydroxide and ether
C. Hydroxyl and ether
D. Hydroxide and ester

Markscheme
C
68. [1 mark]
Which alcohols are oxidized by acidified potassium dichromate(VI) solution when heated?
A. I and II only
B. I and III only
C. II and III only
D. I, II and III

Markscheme
A
69. [1 mark]
Which monomer is used to form the polymer with the following repeating unit?

A. CH3CH=CHCH3
B. CH3CH2CH=CH2
C. CH3CH2CH2CH3
D. (CH3)2C=CH2

Markscheme
A
70. [1 mark]
Which type of reaction occurs when methanol and propanoic acid react together in the
presence of a catalyst?
A. Addition
B. Condensation
C. Redox
D. Neutralization

Markscheme
B

Printed for NASEEM INTL SEC SCH

© International Baccalaureate Organization 2023
International Baccalaureate® - Baccalauréat International® - Bachillerato Internacional®