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Module 4: Core Organic Chemistry
4.1 Basic concepts and hydrocarbons
4.1.1 Basic concepts of organic chemistry
4.1.2 Alkanes
4.1.3 Alkenes
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ebi: 4.1 Basic concepts and hydrocarbons
This section is fundamental to the study of organic chemistry.
This section introduces the various types of structures used routinely in organic
chemistry, nomenclature, and the important concepts of homologous series,
functional groups, isomerism and reaction mechanisms using curly arrows.
The initial ideas are then developed within context of the hydrocarbons: alkanes and
alkenes.
4.1.1 Basic concepts of organic chemistry
Personalised Learning Outcomes (PLCs)
Candidates should be able to apply their knowledge and
understanding to:
Naming and representing the formulae of organic compounds
a) Application of IUPAC rules of nomenclature for systemically naming
organic compounds
@.g. CHsCH2CH(CHs)CHOH has the systematic name: 2-
methybutan-1-ol
eH
Interpretation and use of the terms:
(i) General formula (the simplest algebraic formula of a member
of a homologous series) e.g. for an alkane Cx H 2n2
(ii) Structural formula (the minimal detail that shows the
arrangement of atoms in a molecule) e.g. for butane:
CH3CH2CH2CHs or CHs(CHz)2CHs
(iii) Displayed formula (the relative positioning of atoms and the
bonds between them) e.g, for ethanol: |
H H
(iv) Skeletal formula (the simplified organic formula, shown by
removing hydrogen atoms from alkyl chains, leaving just a
carbon skeleton and associated functional groups) e.g. for
butan-2-ol
OH | Functional Groups
©) Interpretation and use of the terms:
() Homologous series (a series of organic compounds having the
same functional group but with each successive member
differing by CHz)
(ii) Functional group (a group of atoms responsible for the
characteristic reactions of a compound)
(ii) Alkyl group (Ef formula Cx Hon +1 )
(iv) Aliphatic (a compound containing carbon and hydrogen joined
in straight chains, branched chains of non-aromatic rings)
(v)_ Alicylic (an aliphatic compound arranged in non-aromatic rings
with or without side chains)
(vi) Aromatic (a compound containing a benzene ring)
(vil) Saturated (single carbon-carbon bonds only) and unsaturated
(the presence of multiple carbon-carbon bonds, including C=C,
C=C and aromatic rings)
4d) Use of the general formula of a homologous series to predict the
formula of any member of the series
Isomerism
©) Explanation of the term structural isomers (compounds with the same |
molecular formula but different structural formulae) and determination
of possible structural forrnulae of an organic molecule, given its
molecular formula.
Reaction mechamisms
1) The different types of covalent bond fission:
(i) Homolytic fission (in terms of each bonding atom receiving one
electron from the bonded pair, forming two radicals)
(ii) Heterolytic fission (in terms of one bonding atom receiving
both electrons from the bonded pair)
@) The term radical (a species with an unpaired electron) and use of
‘dots’ to represent species that are radicals in mechanisms
‘A ‘curly arrow’ described as the movement of an electron pair,
showing either heterolytic fission of formation of a covient bond
Reaction mechanisms, using diagrams, to show clearly the
movement of an electron pair with ‘curly arrows’ and relevant dipoles. 4.1.2 Alkanes
Personalised Learning Outcomes (PLCs)
Candidates should be able to apply their knowledge and
understanding to:
Properties of alkanes
a)
Alkanes as saturated hydrocarbons containing single C-C and
C-H bonds (overlap of orbitals directly between the bonding
atoms); free rotation of the o- bond
b)
Explanation of the tetrahedral shape and bond angle around
each carbon atom in alkanes in terms of electron pair
repulsion
Explanation of the variations in boiling points of alkanes with
different carbon-chain length and branching, in terms of
induced dipole-dipole interactions (London forces)
Reactions of alkanes
The low reactivity of alkanes with many reagents in terms of
the high bond enthalpy and very low polarity of the o-bonds
present
e)
Complete combustion of alkanes, as used in fuels, and the
incomplete combustion of alkane fuels in the limited ‘supply of
‘oxygen with the resulting potential dangers from CO
The reaction of alkanes with chlorine and bromine by radical
substitution using ultraviolet radiation, including a mechanism
involving homolytic fission and radical reactions in terms of
initiation, propagation and termination
9)
‘The limitations of radical substitution in synthesis by the
formation of a mixture of organic products, in terms of further
substitution and reactions at different positions in a carbon
chain. 4.1.3 Alkenes
Personalised Learning Outcomes (PLCs)
Candidates should be able to apply their knowledge and
understanding to:
Properties of alkenes
a) Alkenes as unsaturated hydrocarbons containing a C=C
bond comprising a T-bond (sideways overlap of adjacent
p-orbitals above and below the bonding C atoms) and a o-
bond (overlap of orbitals directly between the bonding
atoms); restricted rotation of the -bond
b) Explanation of the trigonal planar shape and bond angle
around each carbon in the C=C of alkenes in terms of
electron pair repulsion.
Stereoisomerism in alkenes
©) {) explanation of the terms:
* Stereoisomers (compounds with the same structural formula but
with a different arrangement in space)
* E/Z isomerism ( an example of stereoisomerism, in terms of
restricted totation about a double bond and the requirement for
two different groups to be attached to each carbon of the C=C
gewP) HyC HgC_CHs
po=cl de=ct
H CHs H H
(E)-2-butene (Z-2-butene
+ Cis-trans isomerism (a special case of E/Z isomerism in which
two of the substituent groups attached to each carbon atom of
the C=C group are the same)
(ji) use of the Cahn-Ingold-Prelog (CIP) priority rules to
identity the E and Z stereoisomers
d) Determination of possible E/Z or cis-trans stereoisomers of
an organic molecule, given its structural formula
Addition reactions of alkenes
@) the reactivity of alkenes in terms of the relatively low bond
enthalpy of the m- bond
4) Addition reactions of alkenes with:
() Hydrogen in the prescence of a suitable catalyst
e.g. Ni, to form alkanes
(i) Halogens to form dihaloalkanes, including the use
of bromine to detect the presence of a double C=C.
bond as a test for unsaturation in a carbon chain
(i) Hydrogen halides to form haloalkanes
(iv) Steam in the presence of an acid catalyst, e.g.
HPO, to form alcohols
9) Definition and use of the term electrophile (an electron
pair acceptor)
h) The mechanism of electrophilic addition in alkenes by
heterolytic fission Use of the Markownikof’s rule to predict formation of a
major organic product in addition reactions of H-X to
unsymmetrical alkenes, e.g. H-Br to propene, in terms of
the relative stabilities of carbocation intermediates in the
mechanism
Polymers from alkenes
dD
Addition polymerisation of alkenes and substituted
alkenes, including:
(i) The repeat unit of an addition polymer deduced
from a given monomer
(i) Identification of the monomer that would produce a
given section of an addition polymer
‘Waste polymers and alternatives
K) The benefits for sustainability of processing waste
polymers by:
(i) Combustion for energy production
(i) Use as an organic feedstock for the production of
plastics and other organic chemicals
(iii) Removal of the toxic waste products, e.g. removal
of HCl formed during disposal by combustion of
halogenated plastics (e.g. PVC)
1) The benefits to the environment of development of
biodegradable and photodegradable polymers 10
4 Atom economy and percentage yield are important factors in deciding the sustainability of a
manufacturing process.
(a) Complete the expression below for atom economy.
sum of
atom economy = = x 100%
sum of ... ty
{b) The following five reactions all represent important industrial processes.
Process1 _ CH,CH,CH,CH,CH,CH,CH,CH, —> (CH,),CHCH,CH,CH(CH,),
Process 2 CH,CH,OH + CH;COOH —> CH,COOCH,CH, + H,0
Process3 CH,CH, + H,O —> CH,CH,OH
Process 4 NHj + HNO, —> NH,NOg
Process — CgHyg > CH, + Cty ©
(i) Which process is an example of cracking?
[1]
(li) Which process makes a structural isomer of the reactant?
(ii) Which process does not have an atom economy of 100%?
Explain your answer,
[2]
eocnant 12
5 This question is about the following organic compounds.
CH,CH = CHCH, CH,CH =CH,
S H
You will have to refer to these compounds throughout the question.
(@)_ Explain why compound A is a hydrocarbon.
(b) Which compound is a saturated hydrocarbon?
m1
{c) What is the molecular formula for compound E?
a
(qd) Which compounds are structural isomers of one another?
{1}
e0cn 13
{e) In compound G, there are different shapes around different carbon atoms.
(i) State and explain the shape around carbon atom number 1 in compound G.
(1
(ji) State the shape around carbon atom number 2 in compound G.
1)
() (Which compound shows E/Z isomerism?
1
(li) Explain why some molecules show E/Zisomerism.
2
TURN OVER FOR PART (g)
eae Turn over 2
Answer all the questions.
1 Crude oil is a source of many hydrocarbons.
The skeletal formulae of some of these hydrocarbons are shown below.
G H I
(a) Explain why compound A is both saturated and a hydrocarbon.
(2)
QO
(b) What is the empirical formuta for compound A?
1
{c) Give the letters, A, B, C, D, E, F, G, H or J, of two hydrocarbons that are structural isomers of
each other.
and 1)
s0ce 3
(a) The petroleum industry processes straight chain alkanes into cyclic hydrocarbons such as A,
Bande.
(i) Explain why the petroleum industry processes straight chain alkanes into cyclic
hydrocarbons.
1
(il) Hydrocarbon C can be processed into the cyclic hydrocarbon B.
Construct an equation for this reaction.
a1
(e)_ Explain why hydrocarbon D has a higher boiling point than hydrocarbon C.
() Hydrocarbons G and H are stereoisomers of each other.
Explain what is meant by the term stereoisomerism.
121
(g) Construct the equation for the complete combustion of hydrocarbon C.
[2]
con s012 an 4
(h) A hydrocarbon molecule, CgHy4, is cracked to form an octane molecule and two molecules
of but-2-ene.
Construct the equation for this reaction.
(2) Compound Lis 3-methylheptane. It does not contain a functional group.
i
I
() What is meant by the term functional group?
{1
(ii) Compound I reacts with chlorine in the presence of ultraviolet radiation to give several
structural isomers of C,H,,Cl.
How many structural isomers could be formed in this reaction?
u1
(Ili) The mechanism of the reaction involves radicals.
What is meant by the term radical?
iu]
[Total: 16]
e0ce 2
Answer all the questions.
1 Crude oil is a source of hydrocarbons which can be used as fuels or for processing into
petrochemicals.
Octane, CyHyq, is one of the alkanes present in petrol.
Carbon dioxide is formed during the complete combustion of octane.
ChHig + 12%, —> 8CO, + 9H,O
(@) What is the general formula for an alkane?
{b) Carbon monoxide, CO, is formed during the incomplete combustion of octane.
(2) Write an equation for the incomplete combustion of octane, forming carbon monoxide
and water.
4 a)
(ii) Why does incomplete combustion sometimes take place?
1]
() In cars fitted with a catalytic converter, two toxic gases, CO and NO, react together to form
‘two non-toxic gases.
(i) Write an equation for the reaction between CO and NO in a catalytic converter.
Oi)
(ii) Outline the stages that take place in a catalytic converter to allow CO to react with NO,
a BI 1
Ker
@)
(b)
2
Answer all the questions.
rosene is used as a fuel for aeroplane engines.
Kerosene is obtained from crude oil.
Name the process used to obtain kerosene from crude oll and explain why the process
works.
‘Some of the hydrocarbons in kerosene have the formula CjHyp-
(i) What is the name of the straight chain hydrocarbon with the formula CygHyo?
M1
(ii) Draw the skeletal formula of one branched chain isomer with the formula CjgHo.
f]
(iil) Explain why the straight chain isomer of C,H,» has a highér boiling point than any of its
branched chain structural isomers.
(iv) Explain why the straight chain isomer of C,gH,2 is converted by the petroleum industry
into its branched chain isomers.
MY 3
() When kerosene burns in an aeroplane engine very little carbon monoxide, CO, is formed but
a significant amount of nitrogen monoxide, NO, is formed.
(i) Construct the equation to show the complete combustion of C,¢
2]
(ii) Suggest, with the aid of an equation, how NO is formed within an aeroplane engine.
sessersnenes
(a) NO is 4 radical and contributes towards ozone depletion in the stratosphere.
@ What is a radical?
AT
(il) One of the processes leading to the breakdown of ozone in the stratosphere can be
represented by the following two equations.
NO(g) + On(2) —> NOQ(g) + O2(9)
NO,(g) + O(g) > NO(g) + O,(9)
What is the role of the NO in this process?
[1]
(ii) Ozone in the stratosphere is broken down to make O, and O.
Describe and explain how the concentration of ozone in the stratosphere is maintained.
(iv) Why is it important to life on the Earth's surface that the concentration of ozone in the
stratosphere is maintained?
a
[Total: 15]
ocr Turn over 2
Answer all the questions.
1 The alkanes are an homologous series of hydrocarbons.
The table shows information about some straight chain alkanes.
alkane molecular formula | boiling point/*C |
methane cH, 164
ethane CoHg
propane CoHe
butane CiHt “1
(@) (What is meant by an homologous series?
{a
(li) Explain why the boiling points increase down the alkane homologous series.
‘eocn 3
{b) Alkynes are another homologous series of hydrocarbons.
The table gives the molecular formulae of the first five straight chain alkynes.
@
(ii)
ii)
(iv)
0c
alkyne molecular formula
ethyne C,H
propyne CoH,
but-t-yne C,He
OsHy
hex-t-yne CoHio
Suggest the name of a straight chain alkyne with the molecular formula Cg.
Deduee the general formula for an alkyne.
See ty
The alkynes contain the C=C funetional group.
‘Suggest the displayed formula for propyne.
1)
Hex-1-yne has many cyelic structural isomers.
Draw the skeletal structure of one of these cyclic structural isomers.
m1
Tum over 3
Answer all the questions.
Crude oil is a source of alkanes.
{a) Fractional distillation is used to separate useful hydrocarbons found in crude oil.
Explain, in terms of intermolecular forces, how fractional distillation works.
[21
(b) Tho petroloum industry processes straight-chained alkanes into cycloalkenes such as
cyclopentane and cyclohexane.
Che Ce
2
Heo “Phe Hew “ole
H,C—CH, HO. _CHe
ch,
cyclopentane cyclohexane
()) Deduce the general formula of a eyeloalkane.
1
(ii) Construct the equation to show the formation of cyclohexane from hexane.
M1
(iit) Suggest why the petroleum industry processes hexane into cyclohexane.
e00r Tum over 2
Answer all the questions.
1 Crude oil is a source of many important petrochemicals.
The flow chart shows some of the petrochemicals that can be made and the processes used to
make them.
‘crude oil
fractional distillation
bitumen liquid fuels naphtha} gaseous fuels
2.9. petrol e.g. methane
and diesel and butane
cracking
petrochemicals
‘ihene eg. polymers and
pharmaceuticals
bromoethane ethanol 1,2-dibromoethane
(a) Explain why crude oil can be separated into different fractions.
(b)
e008
1)
Many scientists believe that we should use more fuels such as biodiesel or bio-ethanol rather
than petrol and diesel
Suggest one reason why these scientists take this view.
suseee [1] 2
Answer all the questions.
Crude oil contains many hydrocarbons.
‘The table shows information about some of these hydrocarbons.
(@)
(b)
()
(a)
eoce
Hydrocarbon Molecular formula Boiling point/°C
Hexane Coy 69
3-Methylpentane CoH 63.
2,2-Dimethylbutane Coty 50
What is the empirical formula of hexane?
Explain why hexane is both saturated and a hydrocarbon.
saturated
hydrocarbon
Draw the skeletal formula for 2,2-dimethylbutane.
ny
Describe and explain the trend shown by the bolling points of the hydrocarbons in the table.
(3) 3
(€) Decane, CjgHyp, can be cracked to form hexane and one other product.
Write an equation for this reaction.
(8) In the presence of ultraviolet radiation, butane, C,H,q, reacts with chlorine to form a large
number of organic products.
Several of these products are structural isomers of C,HsClp.
() Write an equation, using molecular formulae, for the formation of C,H,Cl, from butane.
wee [1]
(i) Complete the table below about two of the structural isomers of C,H,Cl,.
isomer 1 Isomer 2
Name 1,4-Dichlorobutane
Displayed formula
[2]
(9) The reaction between butane and chiorine is an example of radical substitution.
Initially, chlorobutane, C,HgCl, is formed, which then reacts with more chlorine to form
C4H,Clp-
(i) The first step of the reaction of C,H_CZ with chlorine is the. homolytic fission of a chlorine
molecule.
What is meant by the term homolytic fission?
(il) Complete the missing species in the propagation steps below.
Cl + OfCl
> OH Cl,
2]
cer Turn over 4
(h)_ Butane, C,H,9, undergoes incomplete combustion when there is @ shortage of exygen.
Write an equation for the incomplete combustion of butane.
1
[Total: 16]
oon 14
7 Inthis question, you are asked to suggest structures for several organic compounds.
{a) Compounds F, G and H are unbranched alkenes that are isomers, each with a relative
molecular mass of 70.0.
‘Compounds F and G are E/Z stereoisomers.
Compound H is a structural isomer of compounds F and G.
+. Explain what is meant by the terms structural isomer and stereoisomer.
+ Explain why some alkenes have E/Zisomerism,
+ Analyse this information to suggest possible structures for compounds F, @ and H.
@ In your answer you should make clear how each structure fits with the information given
above.
1
eee 6
3 Alkenes are unsaturated hydrocarbons used in the industria) production of many organic
compounds.
(@) Complete the flowchart below to show the organic product formed in each addition reaction of
methylpropene.
Bre
mixture of isomers
{4
(b) Curly arrows are used in reaction mechanisms to show the moverent of electron pairs during
chemical reactions.
Use curly arrows to outline the mechanism for the addition reaction of methylpropene with
bromine. The structure of methylpropene has been drawn for you.
Include relevant dipoles in your answer.
H CHs
\
C=C.
AEE
H CHs
00 7
(©) Alkenes can be prepared by the dehydration of alcohols with an acid catalyst.
Cyclohexene can be prepared by the dehydration of cyclohexanol, shown below.
OH
oe + HO
A student reacted 7.65 g of cyclohexanol, CgH,.O, and obtained 0.0268 mol of cyclohexene.
(i) What is the molecular formula of cyclohexene?
eeeereeereal |
(ii) Calculate the percentage yield of cyclohexene,
answer = % (3)
(d) Percentage yield has been used for many years to measure the ‘success’ of a reaction.
200
Recently, chemists have turned their thoughts also to the atom economy of a reaction.
(i) Explain the term atom economy.
11
(il) Cyolohexene can also be prepared by the reaction below.
1-3-0
Explain why the atom economy of this cyclohexene preparation is higher than that from
cyclohexanol in (c).
ssseeaee [2]
[Total: 15)
Turn over 13
(2) Fluoroalkenes are used to make polymers, For example, PVE (CH, i ,CHF),, is used to make
non-flammable interiors of aircraft.
(i) Draw two repeat units of the polymer PVF showing all bonds.
ay
(ii) Draw the structure of the monomer of PVF.
m
(e) Once polymers have been used, they become waste.
Outline two ways that waste polymers are processed usefully, rather than just dumped in
landfill sites.
2)
[otal: 12}
a Turn over 13
(c) Alkenes are used to make addition polymers.
The repeat unit for an addition polymer is shown below.
pu
lL
c
|
CH;
What is the name of the monomer used to make this polymer?
(d) Poly(chloroethene) has the repeat unit below.
H GL
||
‘This repeat unit can be written as —CH,CHCI— .
One way to dispose of poly(chloroethene) is to react it with oxygen at high temperature. This
is called incineration.
(i) Complete the following equation that shows the reaction taking place during
incineration.
—CH,CHCI— + oo 9 CO, +. HO $v HOD [1]
(il) Research chemists have reduced the environmental impact of incineration by removing
the HCI formed from the waste gases.
Suggest a type of reactant that could be used to remove the HCL.
a)
{e) The disposal of polymers causes environmental damage.
Research chemists are developing polymers that will reduce this environmental damage and
increase sustainability.
Describe two ways in which chemists can reduce this environmental damage.
(2
[Total: 14]
eon Turn over 18
5 Alkenes B, C, D, E and F are shown below.
CH,CH, H CH, H. H
a7 ~ Cc. \, of
aN Pon ain
H H H.C H H H
B Cc D
HC. HC. H
c= c= f
H HC H
- F
You will have to refer to these alkenes throughout the question.
(a) Describe, using the orbital overlap model, how the x-bond in alkene D is formed.
[2]
{b) Many alkenes show E/Zisomerism.
(I) Explain why £/Zisomerism is shown in some alkenes.
[2]
(i) Which two alkenes are a pair of E/Zisomers?
Choose from B, C, D, E and F.
and .
i
(c) What is the main organic product of the reaction between alkene D and steam in the presence
of a phosphoric acid catalyst?
off
ocr x 19
(d) Describe and explain the reaction of hydrogen bromide, HBr, with alkene B and with alkene D,
Include in your answer
+ equations and structures of the products,
+ why one of these alkenes gives just one product but the other gives more than one
product,
+ the reaction mechanism for the reaction with alkene D using the curly arrow model
showing any relevant dipoles.
Your answer needs to be clear and well organised using appropriate examples from the
chemistry of alkenes B and D.
[9]
suas Tum over 20
(e) Alkenes are a major source of polymers.
Alkene B can be polymerised.
H. CligCHy
(Draw a section of the resultant polymer showing two repeat units.
(ii) Give the name of this polymer.
M1)
(®) Poly(ethenol) is a very unusual polymer because it can dissolve in water under certain
conditions.
OH H OH H
[2]
(ii) Waste poly(ethenol) does not cause many environmental problems.
Other polymers such as poly(ethene), PVC or PTFE cause significant environmental
problems.
Outline two ways in which waste polymers can be processed to reduce their environmental
impact.
2)
[Total: 21] 4
(©) The flowchart below shows some of the organic compounds that could be made starting from
cyclohexane.
Ch/UV
: “oI
chlorocyciohexane
KOH(aq) /warm
compound a S2%20r(e9) HgPO,/heat
H,80,(a9) Z
OH
cyclohexanol cyclohexene
HBr
Bry
compound B
Br
Br
Explain why cyclohexen is described as unsaturated and as a: hydrocarbon.
[2]
The reaction between chiorine and cyclohexane is an example of radical substitution.
(i)
State one problem of using this reaction to prepare a sample of chlorocyclohexane. The formation of cyclohexanol from chlorocyciohexane involves the reaction of a
nucleophile, the hydroxide ion.
Suggest what feature of the hydroxide fon makes il able to act as a nucleophile.
7
(iv) Using the flowchart, draw the structures of compound A and compound B.
compound A | compound B
[2]
(v) Describe, using the ‘curly arrow model’, the mechanism for the reaction between Br, and
cyclohexene.
Show relevant dipoles and charges.
H,C—CH,
He Phe —_—
c=
ft
H ‘t
Br
Br
4]
(Total: 15]
Turn over
e0cn 7
{c) Poly(tetrafluoroethene), PTFE, and poly(chloroethene), PVC, are halogenated plastics.
(i) Write an equation, using displayed formulae, for the reaction to form PTFE from its
monomer.
(3)
(ii). The Combustion of waste polymers can be used for energy production.
What problem is caused by disposing of PTFE and PVC in this way?
Turn over
‘eoce 22
(d) Unsaturated compounds in plant oils can also be used to make margarine.
Describe how.
[2]
(€) Part of the structure of an unsaturated compound in plant oils is shown below:
~CH,CH,CH=CHCH,CH,—
(1) Draw the displayed formula of the Zisomer of this part of the structure.
La)
(ii) Explain why this part of the structure can have an E and a Zisomer.
2)
[Total: 14]
END OF QUESTION PAPER
oc 16
{h) Compound A is 1-methylcyclohex-1-ene.
A
‘Compound A reacis with H, to give one product and with HBr to give two products.
Draw the structures of the products of these reactions.
ee eee
product of reaction of H, with A
two products of reaction of HBr with A
[3]
[Total: 23]
eon 18
Plastics contain polymer molecules. The disposal of waste plastics is causing many environmental
problems. In the middle of the Pacific Ocean, there is a huge area of sea water contaminated with
very small pieces of plastic waste, In some parts of the Pacific Ocean, there are as many as one
third of a milion of small pieces of plastic waste per square kilometre of ocean,
(a) A short section of one of the polymers found in the Pacific Ocean is shown below.
CoHs
(i) Name and draw the structure of the monomer used to produce this polymer.
name of monomer: ..
structure:
(2)
(ii) The short section of poly(ethenol) is shown below.
4
#
Large quantities of poly(ethene) and poly(ethenol) are disposed of each year.
Poly(ethene) is found as a waste plastic in the Pacific Ocean but poly(ethenol) is not
because it slowly dissolves in water.
Suggest why poly(ethenol) dissolves in water.
[2] 20
8 — Cyclopentene is a cyclic alkene,
(a) The flowchart shows some reactions involving cyclopentene and cyclopentanol.
Complete the partial structures in the boxes to show compounds P, @ and R, the main organic
products of the reactions.
A
AY c
Ot —_
wY\ /™ K,Cr,0,(aq) / HeSO,(aq) (4 Cc
pean eee
ae os ‘OH reflux Vd
cyclopentanol
compound P
i: cnet i :
ee Ye with Ni catalyst c Ne
eee
c= cue
/ \,
4 H
compound @
c—c
cyclopentene
Brg
|
|
{EEE
‘compound R
(b) What would be the colour change in the reaction between cyclopentene and bromine?
‘eon:
[3]
Mi} 24 .
{c) Cyclopentene can be polymerised to give poly(cyclopentene).
Draw a section of poly(cyclopentene) to show two repeat units.
a
(a) Cyclopentene reacts with HCLby-electrophilic addition.
Use the curly arrow model to complete the mechanism for this reaction.
In your answer include any relevant dipoles, the intermediate and the product.
—
i
cl
intermediate
product
[5]
TURN OVER FOR QUESTION 8(e)
Turn over
2008 22
(e) Chlorocyclopentane can be hydrolysed by heating with aqueous sodium hydroxide,
CH Cle
Ho SCH, Ho oe
+ NaOH ——» NEE + NaCl
H,C—CHCt H,C—¢HOH
Use the curly arrow model to complete the mechanism for this hydrolysis reaction,
Include in your answer, relevant dipoles, the name of the mechanism and the type of bond
fission.
A. In your answer you should use the correct technical terms, spelled correctly.
Cle Ho
ne “cH, rc ce
NGEEEE/ a .
Ho G—0 H,C—CHOH
H
HO- products
name of mechanism
[5]
[Total: 15]
type of bond fission ...
END OF QUESTION PAPER 4
(d)_ Ethene can be converted into petrochemicals.
+ Describe how ethene can be converted into 1,2-dibromoethane, bromosthane and
ethanol.
+ Name and describe the mechanism for the conversion of ethene into 1,2-dibromoethane
using the ‘curly arrow’ model.
include any relevant dipoles. 5
(e) Draw and explain the shape of an ethene molecule.
State the H-C-H bond angle in ethene.
a pea eeeseenee [BY
() Addition polymers are made by the polymerisation of alkenes.
E-Pent-2-ene can be made into an addition polymer.
(i) Draw the structure of E-pent-2-ene.
tt]
Draw the structure of poly(pent:2-ene).
Include two repeat units.
t)
[otal: 21)
Turn over
‘e0cn 13
(©) Chioroethene is used to make poly(chloroethene), PVC.
Write an equation, using displayed formulae, for the reaction to form poly(chlorosthene)
from its monomer.
[3]
(d) Waste polymers are often disposed of by combustion. The heat released can be used to
generate electricity.
of PVC.
() Hydrogen chloride, HCI, is a toxic waste product formed by combu:
Suggest how the HCI can be removed from the gases produced during the combustion
of PVC.
{1
(ii) Some waste polymers are put into landifll sites. This uses up a valuable resource,
State two ways, other than landfill and combustion, of processing waste polymers.
2}
Chemists are trying to minimise the environmental damage caused by the disposal of
waste polymers by developing new types of polymers.
Give an example of @ type of polymer being developed to minimise environmental
damage,
(1
(Total: 13)
ocr Turn over 16
7 Compound D reacts by nucleophilic substitution and electrophilic addition.
H H
Nad 4
|
‘cH,—-C—cl
4
compound D
Compound D reacts with KOH(aq) and with HBr(g).
The reaction with KOH(aq) is an example of a nucleophilic substitution and the reaction with
HBr(g) is an example of electrophilic addition.
Describe these two reactions. For each reaction, include:
+ an equation
+ the structure of each organic product
+ the mechanism, using the curly arrow model, showing any relevant dipole
‘+ the type of bond fission that ocours. ‘ANSZNES AHL
© 3NSUALSK0d =
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*HOPHO
oe ay ree e eS
9.0%,
Reaction pathways 119
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Tonal Ta — SPOR OOS NIRV UNS aes srancrouln acces NINA
104N ‘STMULIN THN "ON
SBN suaisa ! No*HOFHO oesueust
Suo*0000%HO svn} Noo
‘SaNIHY <5, —— SaNITIVONOOWH Bemis Taig
HOFHOHO, Sa 7
neet| a r ‘BOUIN BSATS tor Roar
Connor |
agen 20 "avr — | arbor Sacha WH oy
ooo yogmy oes oe ew eaten ARVIN omy = SNOT
TODS POSTEO" | OHOHHD "OSH IPFOHO No ONORHE ji ey Bane
SaNOLY a EMME nooo auwanoo3s
ron Aron ‘Ost wrOHOM wooo ns0240.006
100840 a FWPodH
1 Z
says’ eurepphysuoyconury'z ° revoro rr
=NOOO"HO
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to — 340
hoe" LZ. INSHLATOS
‘BlvildiOSUd JONVEO ore
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: sAemuyed uoloeey
© O
a sren tte iS es 26 This question looks at alkanes
(@)
@00R 2015
Ethane reacts with chiorine by radical substitution.
Describe fully, with equations, the mechanism for this reaction.
(5)
032001 12
SECTION B
Answer all the questions.
21 This question looks at organic halogen compounds.
(a) A section of a halogenated polymer is shown,
CH;H CH;H CH; H
Bee eee Cee aeeeeCeCCE
C=C
ee eeE Seed
H
ca oH clu Cl
Draw the structure of the monomer that could be used to make this polymer.
1]
(ii) Combustion of this polymer produces HCl, which is a toxic gas.
Describe how HCLis removed from the waste gases produced.
1
Polymers made from natural foods such as com starch are replacing
halogenated polymers,
‘An advantage of this is that these polymers do not produce toxic gases on
combustion.
State one other advantage of using polymers made from natural foods.
sessnaseee OY
©00R 2015 032101
pine cel by wande at Uinnan-2618 100929 @) prinar i-Laocleb 600 14
(b) Alkenes can be used to make polymers.
() Phenylethene, CcHsCHCHz, undergoes addition polymerisation.
Write a balanced equation for the addition polymerisation of phenylethene.
‘You should show the structures of the monomer and polymer clearly.
(2)
(ii) Waste polymers are often put into landiil sites.
State one way of processing waste polymers usefully, other than landfill and
recycling.
©.OCR 2016 PRACTICE PAPER hesze2
Printed by nscarle a
On 2018 12:11:36 on printer staffroom-mtd-neree FOL 6 8
SECTION B
Answer all the questions.
16 This question is about unsaturated hydrocarbons.
{a) Compound A and compound B are isomers.
oe a
compound A compound B
Compound A has a lower melting point than compound B.
Suggest why.
ra
{b) Compound C, CH,CH,CH=CHCH,CH,OH, exists as cis and trans stereoisomers.
(i) Name compound C.
ft]
{ii) Define the term stereoisomers.
1
Printed by noearle at 26-Jin-2018 11:65:53 on princar etaltoonalS-uase FOL 6 9
(iii) Draw the structures of the cis and trans stereoisomers of compound C.
cis trans
[2]
(c) The C=C group in an alkene contains a n-bond.
Complete the diagram below to show how p-orbitals are involved in the formation of a a-bond.
Mg, qi! No, eo
a)
ocr 2017 ‘Turn over
Printed by necarle at 29-Jun-2010 21:95:53 en printer staffecen-nfd-varex PCL 6 5
2 Alarge proportion of the world’s output of organic chemicals is used to make addition polymers. These
polymers have a variety of uses.
(a) Poly(propene) is used to make packaging, textiles and rope
‘A repeat unit for poly(propene) is shown below.
(ii) State the bond angle around each carbon.atom in poly(propenc).
(ii) After polymers have been used for packaging, the waste polymers need to be processed to save
resources, for example, by reeyeling
Describe two other ways in which waste poly(propene) can be processed in a sustainable way.
© ocR 2016 o3202 ‘Turn over 2 This question is about alkenes.
(a) Propene, drawn below, contains both o- and n-bonds, The C-H and C-C single bonds are
o-bonds. The C=C double bond is made up of a -bond and a x-bond.
HH
H \f H
NaH
c=c
yes
H H
(i) Describe how a o-bond forms.
seneeneenee 1}
(li) State the bond angle and shape around each carbon atom of the C=C double bond
in propene.
bond angle: ...
shape Heat
ty
(b) Propene reacts with bromine, Bra. in this reaction, bromine acts as an electrophile.
(i) Outline the mechanism of this reaction.
Include curly arrows, relevant dipoles and the structures of the intermediate and final
product(s).
4]
@.00R 2015 os202 5
What does a curly arrow represent in a reaction mechanism?
{c) Pent-1-ene, CHsCH»CH:CH=CH,, is an alkene with molecular formula CsHyo.
(i) Pent-1-ene does not show stereoisomerism.
Explain why.
(ii) A siructural isomer of pent-t-ene shows cis-trans stereoisomerism.
Draw structures for the cis and trans isomers of this structural isomer of pent-1-ene.
eo
‘eis isomer, trans isomer 2
(d) The following molecule shows E/Z isomerism.
FE CH
Nv
c=c
7.
CHC ‘CH,OH
Use the Cahn-Ingold-Prelog priority rules to identify whether this alkene is an E or Z
sterecisomer. Explain how you came to your decision.
. ti)
@ OCR 2015 Hos2/02 Turn over 3
‘Compound A is an alkene.
CHy
f
\
H CH,
compound A
{a) The C=C bond in a molecule of compound A has restricted rotation because it comprises a
bond and am bond.
(i) Describe one difference between the o bond and the x bond.
t
(li) Explain why compound A does not have E/Zisomers.
A structural isomer of compound A has E/Z isomers.
Draw the structure of the Zisomer and then name this isomer.
structure of Zisomer
2]
eocnane
see 690 7
(b) Compound A can be made from alcohol B by heating with an acid catalyst.
‘Suggest two possible structures for alcohol B.
[2]
cnt Turn over 8
(6)* Compound A reacts with hydrogen bromide to form a mixture of two diferent organic products.
HC, CH,
He
/
H CH
compound A
Give the structures of the two possible organic products of the reaction.
Outline the mechanism, using the ‘curly arrow’ model, for the formation of one of the organic
products from compound A.
Explain which of the two organic products is more likely to be formed
coca aie
peony cel Loe moist a. e208 1900259 cp punta MELeaesot 600 16
17 Hydrocarbon D is a structural isomer of CysHz4 used in aviation fuel,
hydrocarbon D
(a) Name hydrocarbon D.
(1)
(b)_ When used in a jet engine, hydrocarbon D undergoes complete combustion as shown in
the equation below:
CrHe + 1702 —> 1100, + 12H,0
hydrocarbon D
(1) During a typical flight in the upper atmosphere:
‘the aircraft burns 80.4 tonnes of hydrocarbon D
+ the temperature outside the aircraft is ~55 °C
+ the pressure is 26.5 kPa
Calculate the volume, in m®, of CO; released during a typical aircraft fight.
Give your answer in standard form and to three significant figures.
volume of COp =...
OCR 2018 PRACTICE PAPER HaszI02
Feinted ky ngosele at 19-An-2018 12:41:16 on printer seatfscon-afdsexc FOL 6 7
(ii) Exhaust gases from an aircraft engine contain nitrogen monoxide.
Write an equation for the formation of nitrogen monoxide in an aircraft engine.
(c)* The hydrocarbon propane can be reacted with chlorine to prepare 2-chloropropane,
CH
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