10.

1
SL
1. 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

2. 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

3. Which compounds belong to the same homologous series?

A. CHCCH2CH3, CHCCH2CH2CH3

B. CH3CH2CH2CH2OH, CH3CH2OCH2CH3

C. CH2CHCH3, CH3CH2CH2CH3
D. CH3COCH3, CH3CH2OCH3

4. How many structural isomers of C6H14 exist?

A. 4

B. 5

C. 6

D. 7

5. 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

6. 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

7. 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

8. 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

9. 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

10. What is the name of this compound, using IUPAC rules?

M18/4/CHEMI/SPM/ENG/TZ2/25

A. 1,1-dimethylpropanoic acid

B. 3,3-dimethylpropanoic acid

C. 2-methylbutanoic acid

D. 3-methylbutanoic acid

11. 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.
12. 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

13. 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
14. Which functional group is surrounded in the molecule?

A. hydroxyl

B. carboxyl

C. carbonyl

D. ether

15. 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

16. Which compound has the lowest boiling point?

A. CH3CH2CH2CH2CH2CH3

B. CH3CH2CH2CH2CH3

C. CH3CH(CH3)CH2CH3

D. CH3C(CH3)2CH3

17. 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

18. Which functional group is present in paracetamol?

A. Carboxyl

B. Amino

C. Nitrile

D. Hydroxyl

19. Which compound contains a secondary carbon atom?

A. CH3CH(Cl)CH(CH3)2

B. (CH3)2CHCH2Cl

C. (CH3)3CCl

D. CH3CH2Cl

20. Which molecule has a tertiary nitrogen?

A. (CH3)2NH

B. (C2H5)4N+I−

C. C3H7N(CH3)2

D. C6H5NH2

21. 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

22. 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

23. What is the order of increasing boiling point for the isomers of C5H12?

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

24. Which compound is not in the same homologous series as the others?

A. C5H12

B. C6H12

C. C7H16

D. C8H18

25. 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

26. What is the general formula of alkynes?

A. CnH2n+2

B. CnH2n

C. CnH2n−2

D. CnHn

27. Which functional groups are present in this molecule?

A. carbonyl, ether, nitrile

B. carbonyl, ester, nitrile

C. carboxyl, ether, amine

D. carboxyl, ester, amine

28. 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

29. 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

30. Which is in the same homologous series as CH3OCH3?

A. CH3COCH3

B. CH3COOCH3

C. CH3CH2CH2OH
D. CH3CH2CH2OCH3

31. Which spectra would show the difference between propan-2-ol,

CH3CH(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

32. 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

33. Which is a homologous series?

A. C2H4, C3H5, C4H6

B. C2H2, C3H4, C4H6

C. C2H2, C2H4, C2H6

D. C2H2, C4H4, C6H6

34. 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

HL
1. Which is a secondary alcohol?

2. Which compounds can be reduced?

I. C2H4
II. CH3COOH
III. CH3CHO

A. I and II only
B. I and III only

C. II and III only

D. I, II and III

3. 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

4. What is the name of this compound using IUPAC rules?

A. 2,3-diethylbutane

B. 2-ethyl-3-methylpentane

C. 3-methyl-4-ethylpentane

D. 3,4-dimethylhexane
5. In which order should the reagents be used to convert benzene into
phenylamine (aniline)?

6. Which functional group is responsible for the p_K_b of 4.1 in this compound?

A. Amido

B. Amino

C. Chloro

D. Ether
7. Which compound has the lowest boiling point?

A. CH3CH2CH2CH2CH2CH3

B. CH3CH2CH2CH2CH3

C. CH3CH(CH3)CH2CH3

D. CH3C(CH3)2CH3

8. What is the major product of the reaction between 2-methylbut-2-ene and

hydrogen bromide?

A. 3-bromo-2-methylbutane

B. 3-bromo-3-methylbutane

C. 2-bromo-3-methylbutane

D. 2-bromo-2-methylbutane

9. Which compound with the molecular formula C4H8O has this high resolution
H1 NMR?

From: libretexts.org. Courtesy of Chris Schaller, Professor (Chemistry)

at College of Saint Benedict/Saint John’sUniversity.

A. but-3-en-2-ol, CH2=CHCH(OH)CH3

B. butanal, CH3CH2CH2CHO
C. butanone, CH3COCH2CH3

D. but-3-en-1-ol, CH2=CHCH2CH2OH

10.2
1. 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

2. 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

3. 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

4. Which describes the reaction between a halogen and ethane?

5. Which molecule will decolorize bromine water in the dark?

A. cyclohexane

B. hexane

C. hex-1-ene

D. hexan-1-ol

6. Which mechanism does benzene most readily undergo?

A. Nucleophilic substitution

B. Electrophilic substitution

C. Electrophilic addition

D. Free radical substitution

7. Which compound can be oxidized when heated with an acidified solution of

potassiumdichromate(VI)?

A. CH3C(O)CH2CH3

B. CH3CH2CH(OH)CH3

C. (CH3)3COH

D. CH3(CH2)2COOH

8. Which type of reaction occurs between an alcohol and a carboxylic acid?

A. Addition

B. Oxidation

C. Esterification

D. Polymerization
9. 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

10. Which monomer would produce the polymer shown?

A. CF3CCl2F

B. CF3CClHF

C. CF2CClF

D. CF2CF2

11. What is formed in a propagation step of the substitution reaction between

bromine and ethane?

A. CH3CH2•

B. CH3CH2CH2CH3

C. H•

D. Br−

12. Which monomer forms the polymer shown?

A.CH(Cl)=CH(CH3)

B. CH2=C(Cl)CH3

C. (CH3)2CHCl

D. CH2=CHCl

13. Which is a propagation step in the free-radical substitution mechanism of

ethane with chlorine?

A. Cl2 → 2 •Cl

B. •C2H5 + Cl2→ C2H5Cl + •Cl

C. •C2H5 + •Cl → C2H5Cl

D. C2H6 + •Cl → C2H5Cl + •H

14. 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

15. 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

16. 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

17.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

18. 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

19. 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

20. 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

21. What is produced when chlorobutane is treated with aqueous sodium

hydroxide solution?

A. butane

B. butanoic acid

C. butanal

D. butan-1-ol

22. Which reaction mechanisms are typical for alcohols and halogenoalkanes?

23. 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–

24. Which combination best describes what is happening to chloromethane,

CH3Cl, 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

25. 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

26. 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

27. 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

28. 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

29. Which compound cannot undergo addition polymerization?

C

30. Which will react with a halogen by an electrophilic substitution mechanism?

31. What type of reaction occurs when C6H13Br becomes C6H13OH?

A. Nucleophilic substitution

B. Electrophilic substitution

C. Radical substitution

D. Addition

HL
1. What is the major product of the reaction between 2-methylbut-2-ene and
hydrogen bromide?
A. 3-bromo-2-methylbutane

B. 3-bromo-3-methylbutane

C. 2-bromo-3-methylbutane

D. 2-bromo-2-methylbutane

2. Which molecule can be oxidized to a carboxylic acid by acidified potassium

dichromate(VI)?

A. Propan-1-ol

B. Propan-2-ol

C. 2-methylpropan-2-ol

D. Propanone

3. Which can be reduced to a secondary alcohol?

A. C2H5COOH

B. CH3CH2OCH3

C. (CH3)2CHCHO

D. CH3COC2H5

4. Which monomer could create this polymer?

A. But-2-ene

B. But-1-ene

C. Propene

D. 2-Methylprop-1-ene
5. Which would be the most effective method to distinguish between liquid
propan-1-ol and propan-2-ol?

A. Observation of colour change when warmed with acidified potassium

dichromate

B. Determination of m/z value of molecular ion in the mass spectrum

C. Determination of percentage composition

D. 1H NMR spectroscopy

6. Which is the correct combination of substitution reaction mechanisms?

7. Which reagents and conditions are best for converting propan-1-ol into
propanoic acid?

A. Reflux with acidified potassium dichromate (VI)

B. Reflux with LiAlH4

C. Distil with acidified potassium dichromate (VI)

D. Distil with LiAlH4

8. Which reaction involves homolytic fission?

A. CH4 + Cl2

B. CH3Br + NaOH

C. (CH3)3CBr + NaOH

D. C6H6 + HNO3 + H2SO4

9. 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

10. 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

11. What must be present on a nucleophile?

A. Negative charge

B. Lone pair of electrons

C. Positive charge

D. Symmetrical distribution of electrons