Y12 Organic Chemistry
Easter homework: Name: ________________________
Combustion of alkanes
Free radical substitution
Class: ________________________
Nucleophilic Substitution
Elimination
Ozone Depletion Date: ________________________
Time: 101 minutes
Marks: 101 marks
Comments:
Page 1 of 14
Q1.
Many hydrocarbon compounds burn readily in air.
(i) Write an equation to show the complete combustion of C15H32
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(ii) One of the gaseous products of the incomplete combustion of methane in gas fires
is known to be poisonous. Identify this product and write an equation for the reaction
in which it is formed from methane.
Identity of product ____________________________________________________
Equation ___________________________________________________________
(Total 4 marks)
Q2.
The burning of fossil fuels can produce atmospheric pollutants.
(a) The combustion of petrol in an internal combustion engine can lead to the formation
of carbon monoxide, CO, and nitrogen monoxide, NO.
(i) Write an equation for the incomplete combustion of octane, C8H18, to produce
CO and water only.
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(ii) State one essential condition for the formation of NO in an engine. Write an
equation for the reaction in which NO is formed.
Condition ______________________________________________________
Equation ______________________________________________________
(3)
(b) All new petrol-engined cars must be fitted with a catalytic converter.
(i) Name one of the metals used as a catalyst in a catalytic converter.
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(ii) Write an equation to show how CO and NO react with each other in a catalytic
converter.
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(2)
Page 2 of 14
(c) State why sulphur dioxide gas is sometimes found in the exhaust gases of petrol-
engined cars. Give one adverse effect of sulphur dioxide on the environment.
Reason for SO2 in exhaust gases ________________________________________
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Environmental effect of SO2 ____________________________________________
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(2)
(Total 7 marks)
Q3.
(a) (i) Name the process used to separate petroleum into fractions.
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(ii) Give the molecular formula for an alkane with nine carbon atoms.
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(iii) Write an equation for the complete combustion of the alkane C11H24
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(iv) Write an equation for the incomplete combustion of C11H24 to produce carbon
and water only.
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(4)
(b) Alkenes can be produced by cracking the naphtha fraction obtained from petroleum.
(i) Write an equation for the thermal cracking of one molecule of C10 H22 to give
one molecule of propene and one molecule of an alkane only.
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(ii) Draw the structure of the chain isomer of but-1-ene.
(2)
Page 3 of 14
(c) The alkanes and the alkenes are examples of homologous series of compounds.
One feature of an homologous series is the gradual change in physical properties
as the relative molecular mass increases. State two other general features of an
homologous series of compounds.
Feature 1 ___________________________________________________________
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Feature 2 ___________________________________________________________
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(2)
(Total 8 marks)
Q4.
The equation below represents a reaction between methane and chlorine.
CH4(g) + Cl2(g) → CH3Cl(g) + HCl(g)
(a) State an essential condition required for this reaction to occur. Explain why this
condition is essential.
Condition ___________________________________________________________
Explanation _________________________________________________________
(2)
(b) (i) State the type of mechanism involved in the above reaction.
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(ii) Name the three types of step involved in this mechanism.
Step 1 ________________________________________________________
Step 2 ________________________________________________________
Step 3 ________________________________________________________
(4)
(c) In addition to CH3Cl, compounds such as CH2Cl2 and CH3CH2Cl may also be formed
when chlorine reacts with methane.
(i) Write equations for the two steps in the mechanism by which CH2Cl2 is formed
from CH3Cl
Equation 1 _____________________________________________________
Equation 2 _____________________________________________________
(ii) Write an equation to represent a step in the mechanism in which CH3CH2Cl is
formed.
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Page 4 of 14
(3) (Total 9 marks)
Q5.
Chlorination of ethane follows a free-radical substitution mechanism. This mechanism is
similar to that which occurs when methane is chlorinated. The overall equation for the
reaction of ethane to form chloroethane is given below.
C2H6 + Cl2 C2H5Cl + HCl
State the conditions and outline a mechanism for this reaction. Show how butane can be
formed in this reaction.
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(Total 5 marks)
Q6.(a) Dichloromethane, CH2Cl2, is one of the products formed when chloromethane, CH3Cl,
reacts with chlorine.
(i) Name the type of mechanism involved in this reaction and write an equation
for each of the steps named below.
Name of type of mechanism _______________________________________
Initiation step
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First propagation step
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Second propagation step
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(ii) Write an overall equation for the formation of dichloromethane from
chloromethane.
Page 5 of 14
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(5)
(b) A compound contains 10.1% carbon and 89.9% chlorine by mass. Calculate the
molecular formula of this compound, given that its relative molecular mass (Mr) is
237.0
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(3)
(c) Suggest the formulae of two bromine-containing organic compounds formed when
dibromomethane, CH2Br2, reacts with bromine.
Compound 1
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Compound 2
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(2)
(Total 10 marks)
Q7.
(a) Name and outline a mechanism for the reaction of 2-bromo-2-methylpropane with
ethanolic potassium hydroxide to form the alkene 2-methylpropene, (CH3)2C=CH2
Name of mechanism __________________________________________________
Mechanism
(4)
(b) Two stereoisomers of but-2-ene are formed when 2-bromobutane reacts with
ethanolic potassium hydroxide.
(i) Explain what is meant by the term stereoisomers.
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Page 6 of 14
(ii) Draw the structures and give the names of the two stereoisomers of
but-2-ene.
Stereoisomer 1 Stereoisomer 2
Name _________________________ Name _________________________
(iii) Name this type of stereoisomerism.
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(5)
(c) When 2-bromo-2-methylpropane reacts with aqueous potassium hydroxide,
2-methylpropan-2-ol is formed as shown by the following equation.
State the role of the hydroxide ions in this reaction.
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(1)
(d) Write an equation for the reaction that occurs when CH3CH2CH2CH2Br reacts with an
excess of ammonia. Name the organic product of this reaction.
Equation ___________________________________________________________
Name of product _____________________________________________________
(3)
(Total 13 marks)
Q8.Nucleophiles react with bromoethane in substitution reactions. This type of reaction is
illustrated in the following scheme.
(a) State what is meant by the term nucleophile.
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Page 7 of 14
(1)
(b) Outline a mechanism for the reaction of potassium cyanide with bromoethane
(Reaction 1).
(2)
(c) Explain why an excess of ammonia is needed in Reaction 2 to produce a high yield
of ethylamine.
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(1)
(d) When potassium hydroxide reacts with bromoethane, ethene can also be formed.
Name and outline a mechanism for this reaction.
Name of mechanism __________________________________________________
Mechanism
(4)
(Total 8 marks)
Page 8 of 14
Q9.
(a) The equation below shows the reaction of 2-bromopropane with an excess of
ammonia.
CH3CHBrCH3 + 2NH3 → CH3CH(NH2)CH3 + NH4Br
Name and outline the mechanism involved.
Name of mechanism __________________________________________________
Mechanism
(5)
(b) When 2-bromopropane is heated with ethanolic potassium hydroxide, an elimination
reaction occurs. State the role of potassium hydroxide and outline a mechanism for
this reaction.
Role of potassium hydroxide ____________________________________________
Mechanism
(5)
(Total 10 marks)
Page 9 of 14
Q10. A student carried out an experiment to study the rates of hydrolysis of some haloalkanes.
(a) In the experiment, two different haloalkanes were placed in separate test tubes
containing silver nitrate solution. The haloalkanes reacted with the water in the silver
nitrate solution. The student timed how long it took for the first appearance of the
silver halide precipitate in each tube at a constant temperature. This time was used
to provide a measure of the initial rate of reaction.
The student obtained the following results.
1-bromobutane 1-iodobutane
Time to form a precipitate / s 480 15
(i) State the meaning of the term hydrolysis.
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(1)
(ii) State the colour of the precipitate formed when iodide ions react with silver
nitrate and write the simplest ionic equation for this reaction.
Colour of precipitate _____________________________________________
Simplest ionic equation
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(2)
(iii) Use your knowledge of the reactions of halide ions with silver nitrate to
suggest why the student did not include 1-fluorobutane in this experiment.
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(2)
(b) The student used the following enthalpy data to try to account for the different initial
rates of hydrolysis of the haloalkanes used in part (a). The student deduced that the
rate of hydrolysis of a haloalkane is influenced by the strength of the carbon–
halogen bond in the haloalkane.
C–Br C–I
Bond enthalpy / kJ mol–1 276 238
State how the experimental evidence enabled the student to make this deduction.
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Page 10 of 14
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(1)
(c) The student had read that the reaction of water with haloalkanes was similar to the
reaction of aqueous sodium hydroxide with haloalkanes and was an example of a
nucleophilic substitution reaction.
(i) State the meaning of the term nucleophile.
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(1)
(ii) When a hydroxide ion collides with a molecule of 1-bromobutane, the following
reaction occurs.
CH3CH2CH2CH2Br + OH– → CH3CH2CH2CH2OH + Br–
Outline the nucleophilic substitution mechanism for this reaction.
(2)
(d) The reaction of hydroxide ions with 2-bromo-2-methylpropane may occur by a
different mechanism from the one in part (c). This different mechanism involves the
formation of a carbocation.
(i) Complete the following equation by drawing the structure of the carbocation
formed when the C–Br bond in 2-bromo-2-methylpropane is broken.
(1)
(ii) Suggest one reason why this reaction occurs by a mechanism involving a
carbocation, but the reaction in part (c) (ii) does not.
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(1)
(Total 11 marks)
Page 11 of 14
Q11.
Trifluoromethane (CHF3) can be used to make the refrigerant
chlorotrifluoromethane(CClF3).
(a) Chlorotrifluoromethane is formed when trifluoromethane reacts with chlorine.
CHF3 + Cl2 CClF3 + HCl
The reaction is a free-radical substitution reaction similar to the reaction of methane
with chlorine.
(i) Write an equation for each of the following steps in the mechanism for the
reaction of CHF3 with Cl2
Initiation step
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First propagation step
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Second propagation step
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Termination step to form hexafluoroethane
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(4)
(ii) Give one essential condition for this reaction.
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(1)
(b) In some refrigeration systems, CHF3 has replaced CClF3 because of concerns about
ozone depletion.
(i) Identify the species formed from CClF3 that is responsible for the catalytic
decomposition of ozone in the upper atmosphere.
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(1)
(ii) Write an overall equation to represent the decomposition of ozone into oxygen.
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(1)
(Total 7 marks)
Page 12 of 14
Q12.
Oxygen and ozone (O3) both occur as gases in the upper atmosphere.
Chlorine atoms catalyse the decomposition of ozone and contribute to the formation of a
hole in the ozone layer.
These chlorine atoms are formed from chlorofluorocarbons (CFCs) such as CF3Cl
(a) (i) Give the IUPAC name of CF3Cl
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(1)
(ii) Complete the following equation that shows the formation of a chlorine atom
from a molecule of CF3Cl
(1)
(iii) State what the • represents in Cl•
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(1)
(b) Write two equations that show how chlorine atoms catalyse the decomposition of
ozone into oxygen.
Equation 1 __________________________________________________________
Equation 2 __________________________________________________________
(2)
(c) An equilibrium is established between oxygen and ozone molecules as shown
below.
3O2(g) 2O3(g) ΔH = +284 kJ mol–1
(i) State Le Chatelier’s principle.
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(1)
Page 13 of 14
(ii) Use Le Chatelier’s principle to explain how an increase in temperature causes
an increase in the equilibrium yield of ozone.
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(2)
(d) Chemists supported the legislation to ban the use of CFCs. Modern refrigerators
use pentane rather than CFCs as refrigerants.
With reference to its formula, state why pentane is a more environmentally
acceptable refrigerant.
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(1)
(Total 9 marks)
Page 14 of 14
