UPPER SECONDARY PURE CHEMISTRY

CHAPTER: Alkanes, Alkenes

Thematic Revision

Alkanes and Alkenes

Summary notes

Alkanes

Definition

Alkanes contain only C-C single bonds and C-H single bonds.

Alkanes are ‘saturated’ as every carbon atom is bonded to its maximum of four atoms.

Alkanes have a general formula of CnH2n+2.

E.g., methane (CH4), ethane (C2H6), propane (C3H8), butane (C4H10)

Physical properties

1) Melting and boiling points

 Increase when number of carbon atoms in alkane increases.

2) Density
 The more the carbon atoms, the higher the density.

3) Volatility
 The more the carbon atoms, the less volatile the compound is.

4) Viscosity
 The more the carbon atoms, the higher the viscosity.

5) Flammability
 The more the carbon atoms, the lower the flammability.

6) Solubility
 Insoluble in water but soluble in organic solvents.
Chemical properties

1) Substitution
 Alkanes will undergo a substitution reaction with halogens (F2, Cl2, Br2 etc…)
in the presence of ultraviolet (UV) light.
 Substitution reaction occurs when atoms are replaced by another atom or
group of atoms. UV light
 E.g., CH4 (g) + Cl2 (g) → CH3Cl (g) + HCl (g)

2) Combustion
 Complete combustion in excess oxygen: products formed are carbon
dioxide and water.
 Incomplete combustion in insufficient oxygen: products formed are carbon
monoxide and water (soot can also be produced).

Isomerism

Isomers are compounds with the same molecular formula but different structural
formula.

Alkanes with at least four carbon atoms will display isomerism.

Alkane Isomers Structural formula

Butane 2

Pentane 3

2,2 - Dimethylpropane
The name of each isomer is obtained based on the longest carbon chain and the
substituent group it contains.

Carbon atoms Prefix Substituent Group

1 Methyl -CH3
2 Ethyl -CH2CH3
3 Propyl -CH2CH2CH3
Alkenes

Definition

Alkenes contain C=C double bonds (C=C is the functional group).

Alkenes are ‘unsaturated’ as some carbon atoms are not bonded to the maximum number
of four atoms. (Able to carry more atoms if the C=C bonds opens up.)

Alkenes have a general formula of CnH2n.

E.g., ethene (C2H4), propene (C3H6), butene (C4H8)

Chemical properties

1) Combustion
 Complete combustion in excess oxygen: products formed are carbon
dioxide and water.
 Incomplete combustion in insufficient oxygen: products formed are
carbon monoxide and water (soot can also be produced).

2) Addition of hydrogen (hydrogenation)

 Condition: Temperature of 200°C with nickel catalyst.
 Through hydrogenation, polyunsaturated compounds (one or more C=C
double bond) can be converted to saturated compounds.
 E.g., through hydrogenation, vegetable oils can be converted to
margarine.

3) Addition of bromine (bromination)

 Aqueous bromine can be used as a test to distinguish between alkanes and
alkenes.
 When aqueous bromine is added to alkenes, the alkene will cause the
aqueous bromine to decolourise from reddish-brown to colourless. Alkane
will not produce any colour change.

4) Addition of water (hydration)

 Hydration occurs when water is added to the C=C double bond to produce
an alcohol containing the −OH functional group.
 Conditions: Temperature of 300°C, pressure 60 atm, with Phosphoric (V)
acid as catalyst.

5) Polymerisation
 Polymerisation is when identical alkene molecules (monomers) join
together to form a single large molecule (polymer).
 C=C bonds are broken in the process.
Production of alkenes (cracking)

1) Catalytic cracking
 Occurs when a long-chain hydrocarbon is broken down into short-chain
hydrocarbons.
 Conditions: Temperature of 600°C, Aluminium oxide (Al2O3) & silicon (IV)
oxide (SiO2) as catalyst.
 An alkene will always be produced. Alkanes & hydrogen may form the other
products from cracking.
 E.g.,
Long chain alkane → shorter chain alkane + alkene
C9H20 → C4H10 + C5H10
Long chain alkane → shorter chain alkene + shorter chain alkene + hydrogen
C9H20 → C4H8 + C5H10 + H2

Industrial applications of cracking

1) Production of fuels for vehicles

2) Production of alkenes

3) Production of hydrogen
Isomerism

Alkene molecules with at least four carbon atoms display isomerism. Isomers have the
same molecular formula but different structural formula.

Addition reactions involving alkene can also create isomers.

Alkene Isomer Structural formula

Butene 3

Butene 4
(after it
undergoes
addition of
water)

Pentene 5
Alkanes and Alkenes
Practice questions

[2022/S4/CCK/SA2/P1/Q35]

1 Which pair of compounds are isomers of each other?

(A)

(B)

__

(C)

(D)

[2022/S4/Greendale/SA2/P1/Q32]

2 Which physical properties of the alkanes does not increase as relative molecular
mass increases?

(A) boiling point

(B) flammability __
(C) melting point
(D) viscosity
[2022/S4/Yishun/SA2/P1/Q34]

3 The table shows the reactions between chlorine and methane.

Which row shows the correct equation and condition of the reaction?

equation condition
(A) Cl2 + CH4 → CH2Cl2 + H2 gases are mixed in the presence of UV light

(B) Cl2 + CH4 → CH2Cl2 + H2 methane is bubbled into aqueous chlorine

__
(C) Cl2 + CH4 → CH3Cl + HCl gases are mixed in the presence of UV light

(D) Cl2 + CH4 → CH3Cl + HCl methane is bubbled into aqueous chlorine

[2022/S4/Christchurch/SA2/P1/Q37]

4 Which one of the following correctly describes both ethene and ethane?

(A) They are both unsaturated hydrocarbons.

(B) They both readily decolourise bromine water. __
(C) They can both burn to produce carbon dioxide and water.
(D) They are both readily polymerised.

[2022/S4/CCK/SA2/P1/Q34]

5 Which of the following mixtures could not be produced when heptane, C7H16 is
cracked?

(A) propene + butane

(B) propane + butene __
(C) propane + butane + hydrogen
(D) butene + propene + hydrogen

[2022/S4/CCK/SA2/P1/Q37]

6 The number of C=C bonds in a vegetable oil can be found by reacting the oil with
aqueous bromine.

0.02 moles of vegetable oil was found to react completely with 19.2 g of aqueous
bromine.

How many C=C bonds are there in one molecule of vegetable oil?

(A) 2
__
(B) 6
(C) 8
(D) 12
[2022/S4/Greendale/SA2/P1/Q40]

7 Structures 1, 2, 3 and 4 are hydrocarbons.

Which pair of structures are isomers?

(A) 1 and 2
(B) 1 and 4
__
(C) 2 and 3
(D) 2 and 4
[2022/S4/Guangyang/SA2/P1/Q32]

8 A hydrocarbon, CxHy, undergoes an addition reaction with chlorine.

A second hydrocarbon, CpHq, undergoes a substitution reaction with chlorine.

If x = 4 and p = 6, what are the values of y and q?

y q
(A) 8 16
(B) 8 14
(C) 10 12
__
(D) 10 14

[2022/S4/CCK/SA2/P1/Q39]

9 Which property does not change when ethene undergoes polymerisation to form
poly(ethene)?

(A) boiling point

(B) empirical formula
(C) molecular mass __
(D) molecular formula

[2022/S4/Greendale/SA2/P1/Q33]

10 When 20 cm3 of a gaseous alkene burns in an excess of oxygen, 60 cm3 of carbon

dioxide are formed. Both volumes are measured at r.t.p.

What is the formula of the alkene?

(A) C3H6
(B) C3H8
(C) C6H12 __
(D) C6H14
Question 3 [2022/S4/Broadrick/SA2/P2/Q3]

The table shows the names and structures of some hydrocarbons.

number
of carbon alkanes cycloalkane alkene
atoms

pentane cyclopentane pentene

hexane cyclohexane hexene

heptane cycloheptane heptene

(a) Cycloalkanes are an example of a homologous series.

(i) Explain how the formulae of cycloalkanes in the table show this. [1]

(ii) Suggest two differences in physical properties between cyclopentane and

cycloheptane. [2]
 (iii) The molecular formula of hexadecane is C16H34.

Give the molecular formula for cyclohexadecane. [1]

(b) (i) Are cycloalkanes isomers of alkanes? Explain your reasoning. [1]

(ii) Draw the structure of a branched chain isomer of hexane which is a straight
chain alkane with the formula C6H14.[1]
(c) The percentage of carbon and hydrogen in some molecules are shown in the table.

percentage of
name of percentage of
hydrogen by
molecule carbon by mass
mass

hexane 84 16

hexene 86 14

cycloheptane 86 14

Explain why the percentages of carbon and hydrogen are the same for hexene and
cycloheptane, but different for hexane. [2]

(d) Bromine water can be used in a test to distinguish between cycloalkanes and
alkenes.

Describe the results that would be obtained if this test is carried out on separate
samples of cyclooctane and octene. [2]
Question 10 [2022/S4/Serangoon/SA2/P2/Q10]

In the table below shows a list of members found in the ketones homologous series.

molecular boiling point

name structural formula
formula (oC)

propanone C3H6O 56.2

butanone C4H8O 79.6

pentanone C5H10O 102

hexanone C6H12O

(a) Draw the structural formula and write the name of the next member after
hexanone. [2]
(b) What is the general formula of the ketones homologous series? [1]

(c) Draw an isomer of butanone. [1]

(d) Suggest the boiling point of hexanone.

Explain your answer in terms of bonding and structure. [3]

(e) Ketones and alkenes both undergo addition reactions as shown by the structural
equations shown below.

Alkene: Propene reaction with water

Ketone: Propanone reaction with water

(i) Describe two differences between the two addition reactions shown above.
[2]

(ii) State and explain what would be observed when a few drops of Universal
indicator are added into propanone. [1]