10.

2 Functional Group Chemistry

1. [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

2. [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

3. [1 mark]

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

A. Addition

B. Oxidation

C. Esterification

D. Polymerization

4. [1 mark]

Which describes the reaction between a halogen and ethane?

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5. [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

6. [1 mark]

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

7. [1 mark]

Which compound can both be esterified and turn acidified potassium dichromate(VI) solution green?

A. (CH3)3COH

B. CH3CH2CO2H

C. (CH3)2CHOH

D. CH3CH2COCH3

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8. [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

9. [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

10. [1 mark]

What is the mechanism of the reaction between ethane and chlorine in sunlight?

A. Free radical substitution

B. Free radical addition

C. Electrophilic substitution

D. Electrophilic addition

11. [1 mark]

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 Which species can oxidize ethanol to ethanoic acid?

A.

B. Fe

C.

D. Acidified

12. [1 mark]

Which compound could be X in the two-stage reaction pathway?

A.

B.

C.

D.

13. [1 mark]

Which statements about the chlorine free radical are correct?

I. It has 18 electrons.

II. It is an uncharged species.

III. It is formed by homolytic fission.

A. I and II only

B. I and III only

C. II and III only

D. I, II and III

14. [1 mark]

Which statement is correct about the polymerization of ethene to poly(ethene)?

A. The polymer is an alkene.

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 B. The monomer ethene and the repeating unit have the same empirical formula.

C. The monomer ethene is less reactive than the polymer.

D. The polymer contains C−C single and C=C double bonds.

15. [1 mark]

Which statements are correct for the reaction of ethene with bromine in the absence of ultraviolet
light?

I. It is an addition reaction.

II. The organic product is colourless.

III. The organic product is saturated.

A. I and II only

B. I and III only

C. II and III only

D. I, II and III

16. [1 mark]

What is the product of the addition of chlorine, , to propene, ?

A. 1,1-dichloropropane

B. 2,2-dichloropropane

C. 1,2-dichloropropane

D. 1,3-dichloropropane

17. [1 mark]

Which equation represents a propagation step in the reaction of methane with bromine?

A.

B.

C.

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 D.

18. [1 mark]

For the reaction pathway below, what are the names for the first and second steps?

19. [1 mark]

Which product is formed when bromine water is added to propene, ?

A.

B.

C.

D.

20. [1 mark]

Which of these repeating units is present in the polymer poly(propene)?

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21. [1 mark]

What is the structural formula of the ester formed by reacting propanoic acid with 2-methylbutan-2-ol
under appropriate conditions?

22. [1 mark]

What is the function of the ultraviolet light used in the reaction between ethane and bromine?

A. It causes bromine free radicals to form bromine molecules.

B. It causes bromide ions to form bromine molecules.

C. It causes bromine molecules to form bromide ions.

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 D. It causes bromine molecules to form bromine free radicals.

23. [1 mark]

Which organic product forms in the following reaction?

A. Ethanoic acid

B. Propanal

C. Propanone

D. Propanoic acid

24. [1 mark]

Which steps are involved in the free-radical mechanism of the bromination of ethane in the presence of
ultraviolet radiation?

I.

II.

III.

A. I and II only

B. I and III only

C. II and III only

D. I, II and III

25. [1 mark]

Which substance can be polymerized to produce the polymer below?

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 A. But-1-ene

B. But-2-ene

C. Propene

D. 2-methylpropene

26. [1 mark]

What are possible products of the incomplete combustion of propane?

A. carbon monoxide, hydrogen and carbon

B. carbon dioxide, carbon and hydrogen

C. carbon, carbon monoxide and water

D. carbon dioxide and water only

27. [1 mark]

Which equation represents a propagation step in the mechanism for the reaction between ethane,
, and chlorine, , in the presence of sunlight/UV?

A.

B.

C.

D.

28. [1 mark]

What is the organic product of the reaction between butan-1-ol and ethanoic acid on heating using
concentrated sulfuric acid?

A. Butyl methanoate
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 B. Butyl ethanoate

C. Ethyl butanoate

D. Ethyl propanoate

29. [1 mark]

What are possible products of the incomplete combustion of propan-2-ol?

A. carbon monoxide, hydrogen and carbon

B. carbon dioxide, carbon and hydrogen

C. carbon, carbon monoxide and water

D. carbon dioxide and water only

30a. [1 mark]

This question is about carbon and chlorine compounds.

Ethane, C2H6, reacts with chlorine in sunlight. State the type of this reaction and the name of the
mechanism by which it occurs.

30b. [3 marks]

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 Formulate equations for the two propagation steps and one termination step in the formation of
chloroethane from ethane.

30c. [1 mark]

Chloroethene, C2H3Cl, can undergo polymerization. Draw a section of the polymer with three repeating
units.

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31a. [3 marks]

The photochemical chlorination of methane can occur at low temperature.

Using relevant equations, show the initiation and the propagation steps for this reaction.

31b. [1 mark]

Bromine was added to hexane, hex-1-ene and benzene. Identify the compound(s) which will react with
bromine in a well-lit laboratory.

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31c. [1 mark]

Polyvinyl chloride (PVC) is a polymer with the following structure.

State the structural formula for the monomer of PVC.

32a. [1 mark]

Propane and propene are members of different homologous series.

Draw the full structural formulas of propane and propene.

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32b. [4 marks]

Both propane and propene react with bromine.

(i) State an equation and the condition required for the reaction of 1 mol of propane with 1 mol of
bromine.

(ii) State an equation for the reaction of 1 mol of propene with 1 mol of bromine.

(iii) State the type of each reaction with bromine.

Propane:

Propene:

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33a. [4 marks]

A hydrocarbon has the empirical formula . When 1.17 g of the compound is heated to 85 °C at a
pressure of 101 kPa it occupies a volume of .

(i) Calculate the molar mass of the compound, showing your working.

(ii) Deduce the molecular formula of the compound.

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33b. [2 marks]

exists as three isomers. Identify the structure of the isomer with the lowest boiling point and
explain your choice.

33c. [2 marks]

Ethanol is a primary alcohol that can be oxidized by acidified potassium dichromate(VI). Distinguish
between the reaction conditions needed to produce ethanal and ethanoic acid.

Ethanal:

Ethanoic acid:

33d. [1 mark]
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 Deduce the half-equation for the oxidation of ethanol to ethanal.

34a. [1 mark]

Some reactions of but-2-ene are given below.

Deduce the full structural formula of compound A.

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34b. [1 mark]

Apply IUPAC rules to name compound A.

34c. [1 mark]

Describe the colour change observed when excess but-2-ene reacts with bromine to form compound A.

34d. [2 marks]

State the names of the reagents D and E.

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34e. [3 marks]

(i) Outline two reasons why the polymerization of alkenes is of economic importance.

(ii) Identify the structure of the repeating unit of poly(but-2-ene).

34f. [2 marks]

Compound C, , can also be formed directly from compound B, .

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 (i) State the reagent and the conditions required for this reaction.

(ii) State the name of the type of reaction occurring in this conversion.

34g. [2 marks]

Compound C can be oxidized by acidified potassium dichromate(VI) to form compound F.

(i) State the name of the functional group present in compound F.

(ii) Deduce the structural formula of an alcohol which is a structural isomer of compound C and cannot
be oxidized by acidified potassium dichromate(VI).

34h. [2 marks]

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 Explain why but-2-ene is more volatile than compound C, .

34i. [1 mark]

Deduce the equation for the complete combustion of compound C.

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