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Dunman High School

2011 Year 5 H2 Chemistry


Tutorial 11: Alkanes

Reactivity
3. For each of the following, state whether or not you expect any reaction to occur to any
significant extent. Fully describe and write equations for any reactions which would be
expected to occur.
(a) Sodium metal is added to warm hexane.
No reaction
(b) Chlorine and hexane vapour are heated in the dark.
No reaction

(c) Heptane and hydrogen being heated in sunlight.


No reaction
(d) Ethane was allowed to react with an excess of oxygen.

Complete Combustion:
7
C2H6 (g) + O (g)  2CO2 (g) + 3H2O (l)
2 2
(e) Nonane was reacted with a limited supply of oxygen.

Incompletion Combustion:
C9H20 (l) + 19 O2  9CO (g) + 10H2O (l)
2

Combustion
4 For complete combustion, 1 mole of alkane was found to require 5 moles of oxygen.
Give the possible formula of this hydrocarbon.

Let the general formula of the alkane be CnH2n+2.


3n  1
CnH2n+2 + O2  nCO2 + (n + 1) H2O
2
3n  1
 =5  n = 3
2

Formula of hydrocarbon is C3H8.


2011 DHS Year 5 H2 Chemistry
3 3
5. A mixture of 10 cm of a gaseous hydrocarbon and 100 cm of oxygen was exploded.
The volume after the explosion was 75 cm3 and this was reduced to 35 cm3 on treatment
with potassium hydroxide solution. Deduce the molecular formula of the hydrocarbon and
give its possible structural formula. (Assume all measurements were made at r.t.p.)

y y
CxHy (g) + (x + ) O2 (g)  xCO2 (g) + H O (l)
4 2 2
10cm3 100 cm3

Volume of CO2 reacted with KOH solution = 75 –35 = 40 cm3


Volume of excess O2 = 75 – 40 (i.e. CO2) = 35 cm3
Volume of O2 used in combustion = 100 – 35 (i.e. CO2) = 65 cm3

CxHy ≡ x CO2 CxHy ≡ (x + y


) O2
10cm3 40cm3 4

x 40 10cm3 65cm3
= x  y
1 10 4 65
x = 4 =
1 10
4x  y
= 6.5
4
4x+y = 26
y = 10

Molecular formula of hydrocarbon: C4H10.

Possible structural formula: CH3CH2CH2CH3.

Free Radical Substitution Mechanism


6. When propane reacts with chlorine, two different mono–chloropropanes are produced.
(a) State the type of substitution reaction occurring.

Free–radical substitution reaction.


(b) What conditions are used for the reaction?

Presence of ultraviolet light.

Alkanes Tutorial 2
2011 DHS Year 5 H2 Chemistry

(c) Briefly describe what happens and write any equations for reactions that occur in this
reaction.
Step 1: Initiation
 Chlorine is supplied with energy (ultraviolet light) to split into free
radicals via homolytic fission of Cl – Cl bond.
UV light
Cl – Cl Cl + Cl (slow step)

Step 2: Propagation
 Highly reactive chlorine radicals collide with propane molecules and
abstract one of its hydrogen atoms leaving another free radical.

Cl + CH3CH2CH3  CH3CH2CH2 + HCl


CH3CH2CH2 + Cl2  CH3CH2CH2Cl + Cl

 The free chlorine radical reacts with another molecule and the
chain reaction continues

Step 3: Termination
 The chain reaction ends when two free radicals collide and
combine to form a stable product, i.e. no reactive free radicals
present.
Cl + Cl  Cl2
CH3CH2CH2 + Cl  CH3CH2CH2Cl
CH3CH2CH2 + CH3CH2CH2  CH3(CH2)4CH3
(d) State the type of isomerism exhibited by the two different mono–chloropropanes.

Positional isomerism
(e) Draw the structural formula of each of the two isomeric products. Suggest (with a reason)
in what ratio they might be formed.
Isomers: 1–chloropropane and 2–chloropropane
H H H H H H
H C C C H H C C C H
Cl H H H Cl H

1–chloropropane has 6Hs that can be substituted by chlorine free


radicals while 2–chloropropane has only 2 Hs.
Thus ratio is 3:1.
Alkanes Tutorial 3
2011 DHS Year 5 H2 Chemistry

*(f) In a separate experiment, a sample of propane was reacted with bromine under sunlight
to yield disubstituted halogenoalkanes as products.
(i) Draw the displayed formula of all possible products and name them.

Isomers:
1,1–dibromopropane 2,2–dibromopropane
Br H H H Br H
H C C C H H C C C H
Br H H H Br H

1,2–dibromopropane 1,3–dibromopropane

H H H H H H
H C C C H H C C C H
Br Br H Br H Br

(ii) State and outline the mechanism for this reaction.

Mechanism: Free–Radical Substitution


Step 1: Initiation
 Bromine is supplied with energy (ultraviolet light) to split into free
radicals via homolytic fission of Br–Br bond.
UV light
Br – Br Br + Br (slow step)

Step 2: Propagation
 Highly reactive bromine radicals collide with propane molecules and
abstract one of its hydrogen atoms leaving another free radical.

Br + CH3CH2CH3  CH3CH2CH2 + HBr


CH3CH2CH2 + Br2  CH3CH2CH2Br + Br

Br + CH3CH2CH2Br  CH3CH2CHBr + HBr


CH3CH2CHBr + Br2  CH3CH2CHBr2 + Br

Alkanes Tutorial 4
2011 DHS Year 5 H2 Chemistry

 The free bromine radical reacts with another molecule and the
chain reaction continues

Step 3: Termination
 The chain reaction ends when two free radicals collide and
combine to form a stable product, i.e. no reactive free radicals
present.
Br + Br  Br2
CH3CH2CH2 + Br  CH3CH2CH2Br
CH3CH2CH2 + CH3CH2CH2  CH3(CH2)4CH3
CH3CH2CHBr + Br  CH3CH2CHBr2
7. If a few drops of bromine are added to pentane a deep red solution is formed. No
reaction occurs if the mixture is kept in the dark, but in sunlight the red colour slowly
disappears and a misty gas is given off.
* the misty colourless gas formed in the reaction.

HBr (Hydrogen bromide)


(b) Write an overall equation for the reaction of one mole of bromine with one mole of
pentane under these conditions and identify the type of reaction taking place.

CH3CH2CH2CH2CH3 + Br2  CH3CH2CH2CH2CH2Br + HBr

Type of reaction: Free–radical substitution


(c) Why does the reaction only occur in sunlight?

Energy from ultraviolet light (in sunlight) causes homolytic fission of Br–
Br bond to occur and this leads to the formation of chlorine free
radicals, Br .

Alkanes Tutorial 5
2011 DHS Year 5 H2 Chemistry

Nomenclature (Self–Attempt)
1. Name the following alkanes:

(a) CH3CH2CH2CH2CH2CH3 (c)

n–hexane ethylcylopentane
CH3 CH2CH3
CH3CHCH2CHCH2CH3
(b) (d)

4–ethyl–2–methylhexane methylcyclopropane
2 Write the full structural formula of the following alkanes:
(a) ethylcyclohexane (d) 3,4–diethyl–2,2–dimethylheptane

H H H
H H H
C C
H C C C H
H H
C C H
C H
H H
H H

(b) 1,2–dimethylcyclopentane (e) 2–chloro–3–methylhexane

H H H
H H
C C
H C C H
H
C C H
H C
H H H
H

(c) 2,2,3–trimethylbutane (f) 2–bromo–2–chloroheptane

Alkanes Tutorial 6