(CSEC Chemistry) Section B Notes and ESQs

CSEC CHEMISTRY / SECTION B – ORGANIC CHEMISTRY
1. Sources of Hydrocarbon Compounds

Typical Exam Question / 2017 CSEC Chemistry Paper 01 Typical Exam Question / 2012 CSEC Chemistry Paper 02
Which of the following is a natural source of hydrocarbons? a) Hydrocarbons are compounds that contain the
elements hydrogen and carbon. Name TWO
(A) Carbon
natural sources of hydrocarbons. (2 mks)
(B) Methane
b) Fractional distillation of crude oil produces several
(C) Hydrogen
fractions, containing a range of compounds with
(D) Petroleum
varying numbers of carbon atoms. Three of these
Typical Exam Question / 2003 CSEC Chemistry Paper 01 fractions are shown in Table 3.
The process by which large molecules of hydrocarbon are

broken up into smaller molecules is called
(A) saponification
(B) cracking (i) State the name of Fraction 1 OR Fraction 3.
(C) polymerization (1 mk)
(D) condensation (ii) State ONE use of Fraction 2. (1 mk)
See answers in the ‘Exam-style questions’ section

Candidates should be able to:
• identify natural gas and petroleum as natural sources of hydrocarbons;

• list the main uses of at least three fractions obtained from the fractional distillation of petroleum;
o Uses should include fuels, petrochemicals, lubricants.
o Refer to SO A2.5.
• describe cracking of petroleum fractions.
o Thermal and catalytic cracking of alkanes.

HYDROCARBONS
hydrocarbons
A hydrocarbon is any member of a class of organic chemical compounds composed only of the elements
carbon and hydrogen. They serve as fuels and lubricants as well as raw materials for the production of
plastics, fibres, rubbers, solvents, explosives, and industrial chemicals. Naturally occurring hydrocarbons are
extracted from deep under the Earth’s surface where they exist in both the gaseous form (natural gas) and
liquid form (petroleum/crude oil).
Natural gas
Natural gas is a mixture of mainly methane CH4 along with small amounts of ethane C2H6, propane C3H8, and
butane C4H10. Before it is sold commercially, propane and butane are removed and liquefied to produced
liquefied petroleum gas (LPG or bottled gas). The mixture that remains consists of methane and ethane.
Components of natural gas
Petroleum
Petroleum/crude oil is an oily, smelly mixture of hundreds of different organic compounds, mainly alkanes
and ringed hydrocarbons. It is formed from the remains of dead organisms that fell to the ocean floor and
were buried under thick sediment. High pressures slowly converted them to petroleum over millions of
years.
Petroleum is an important source of fuels (such as petrol, diesel, and kerosene), lubricants, as well as
feedstock (= raw materials used to provide reactants for an industrial reaction) for the petrochemical
industry (for example, ethene is produced from petroleum and used as feedstock to make polyethene).
To be useful, petroleum must be separated into its different components called fractions. This is done by
fractional distillation at an oil refinery.

Fractional distillation of petroleum
Fractional distillation is used to separate petroleum into simpler, more useful mixtures. This method can be
used because different hydrocarbons have different boiling points. Refer to A2. Mixtures and Separations.
When it is first removed from under the ground, impurities are removed from the petroleum and it is heated
to about 400℃. The liquid and vapour produced are piped into the lower part of a fractionating tower. The
vapours rise up the tower and the viscous
liquid fraction, known as bitumen or asphalt,
sinks to the bottom of the tower and is
tapped off.
The vapours rising up the tower pass

through a series of bubble caps and trays
where they may condense. The temperature
of the tower decreases upwards, so the
vapours of the larger hydrocarbons with the
higher boiling points condense on the bubble
caps in the lower part of the tower, whereas
smaller hydrocarbons with lower boiling
points rise further and condense at higher
levels. The liquids produced are tapped off
from the trays at the different levels in the
tower. Gases that do not condense at the
temperatures within the tower are removed
at the top of the tower as refinery gas.
Each fraction in this process is a mixture of

hydrocarbons of similar molecular size and
boiling points within a specific range.
Fraction Boiling point (℃) Number of carbon atoms

Refinery gas below 25 1-4
Petrol (Gasoline) 25-170 5-10
Kerosene oil (paraffin oil) 170-250 10-14
Diesel oil 250-350 14-20
Fuel oil, lubricating oil, and waxes 350-400 18-30
Bitumen Above 400 more than 30

Cracking
Cracking is the process by which long chain hydrocarbon molecules are broken down into shorter chain
hydrocarbon molecules by breaking carbon-carbon bonds.
Cracking is important because after fractional distillation of petroleum, (1) short-chain hydrocarbon
molecules such as petrol are in greater demand than longer ones such as diesel oil and (2) most
hydrocarbons obtained from petroleum only have carbon-carbon single bonds and are fairly unreactive –
they must be converted into more reactive compounds which have carbon-carbon double bonds to be used
in the petrochemical industry to manufacture everyday organic compounds.
It can be carried out in one of two ways: thermal cracking or catalytic cracking.
Thermal cracking
During thermal cracking, larger alkanes are broken into smaller ones with temperatures above 700℃ and
pressures up to 70 atmospheres. Under these conditions, long-chain alkane molecules vibrate strongly
enough to brake, forming a shorter-chain alkane and at least one alkene.
The molecules are broken in a fairly random way, so a variety of products can be formed. For example,
octane C8H18 can be cracked in a variety of ways:
Catalytic cracking
During catalytic cracking, long-chain alkanes are heated to temperatures of about 500℃ at fairly low
pressures in the presence of a catalyst (normally synthetic mixtures of aluminium oxide and silicon dioxide,
known as zeolites). This method is the most important source of petrol and raw materials for the
petrochemical industry.

EXAM-STYLE QUESTIONS
exam-style questions
OF A
Which of the following is a natural source of hydrocarbons? (i) Hydrocarbons are compounds that contain the
elements hydrogen and carbon. Name TWO
(A) Carbon
natural sources of hydrocarbons. (2 mks)
(B) Methane
(ii) Fractional distillation of crude oil produces several
(C) Hydrogen
fractions, containing a range of compounds with
(D) Petroleum
varying numbers of carbon atoms. Three of these
The answer is (D) Petroleum. fractions are shown in Table 3.
Typical Exam Question / 2003 CSEC Chemistry Paper 01
The process by which large molecules of hydrocarbon are

broken up into smaller molecules is called
a) State the name of Fraction 1 OR Fraction 3.
(A) saponification (1 mk)
(B) cracking b) State ONE use of Fraction 2. (1 mk)
(C) polymerization
i/Petroleum/crude oil and natural gas (+ peat, coal)
(D) condensation
ii/a/Fraction 1: refinery gas; Fraction 3: bitumen/asphalt
The answer is (B) cracking.
b/ fuel for jets, cooking, lighting
2007 CSEC Chemistry Paper 01
Which hydrocarbon is the major constituent of natural gas?
The first stage in the process of refining crude oil to
(A) Methane
produce more value-added products is fractional
(B) Ethane
distillation.
(C) Propane
(D) Butane (i) Name the property of compounds upon which
fractional distillation is based. (1 mk)
The answer is (A) Methane.
(ii) Name the lightest and heaviest fractions that
are usually obtained from the fractional
distillation of crude oil. (2 mks)
(iii) State ONE use of EACH of the fractions named
in (ii) above. (2 mks)
i/boiling points
ii/lightest: natural gas; heaviest: bitumen
iii/resp.: cooking gas; paving roads, roofing material


2014 CSEC Chemistry Paper 01 2016 CSEC Chemistry Paper 02
These items refer to the following options. Heavy oil fractions with a high carbon content can be
subjected to breakdown through either catalytic or
(A) Bitumen
thermal cracking.
(B) Paraffin oil
(C) Methane (i) Define the term ‘cracking’. (1 mk)
(D) Propene (ii) How does catalytic cracking differ from thermal
cracking?
The residue in the fractional distillation of petroleum
i/the process by which large molecules of hydrocarbon
The answer is (A) Bitumen.
are broken up into smaller molecules by breaking
Is a MAJOR constituent of natural gas carbon-carbon bonds
The answer is (C) Methane. ii/thermal cracking involves heating alkanes to

temperatures above 700degC and pressures up to 70
atm so they vibrate and break; catalytic cracking involves
heating alkanes to temperatures of about 500degC at
fairly low pressures in the presence of a catalyst
(normally a zeolite)
2. Organic Chemistry – An Introduction

Which of the following is the fully displayed structural The fully displayed structures for two hydrocarbons,
formula of 2-bromobutane? Compound A and Compound B, are shown below.
(A)
(B)
(i) Name the homologous series to which Compounds
A and B belong.
(C) (ii) State the name of EACH compound.
(iii) Define ‘structural isomerism’.
(iv) Draw the FULLY DISPLAYED structure of ONE
(D) structural isomer for EACH of Compounds A and B.

• illustrate that carbon atoms can form single and double bonds, branched and unbranched chains,
and ring compounds;
o Carbon atoms form four bonds.
• write formulae to represent simple organic compounds;
o Structures to be represented by the condensed formulae
CH3CH2CH2CH3 and fully displayed (structural) formulae:
• list the general characteristics of a homologous series;
• write general and molecular formulae for members of a given homologous series;
o Alkanes, alkenes, alcohols, and alkanoic (carboxylic) acid.
• deduce the homologous series given the fully displayed and condensed formulae of compounds;
• write fully displayed structures and names of branched and unbranched alkanes and unbranched
alkenes, alcohols, and alkanoic acids;
o IUPAC notation structure limited to compounds of up to 6 carbon atoms.
• define structural isomerism;
• write the fully displayed structures of isomers given their molecular formulae.
o Limit to structural isomerism for alkanes and alkenes up to 6 carbon atoms.

ORGANIC
organicCOMPOUNDS
compounds
Organic chemistry is the study of compounds which contain carbon, generally known as organic compounds
(with the exceptions of carbides, carbonates, cyanides, and carbon oxides).
Most organic compounds also contain hydrogen, many contain oxygen, and some contain other elements
such as nitrogen, sulphur, and phosphorus. Organic compounds which contain only carbon and hydrogen are
hydrocarbons.
The formulae of organic compounds can be written in a variety of ways. Among the most common methods
are:
• the molecular formula, which shows the total number of atoms of each element in one molecule of
the compound.
• the fully displayed structural formula, which shows in two-dimensional diagrammatic form how the
atoms are arranged in one molecule of the compound. However, the fully displayed formula is a
two-dimensional drawing of a three-dimensional molecule; the ball-and-stick model represents the
actual molecule in three dimensions.
• the condensed structural formula, which shows the sequence and arrangement of atoms in one
molecule of the compound in such a way that the nature and position of attachment of the
functional group is shown without drawing the molecule. Each carbon atom is written separately and
in sequence, followed by the other atoms that are bonded to it. This may be shortened further by
showing the total number of carbon atoms and the total number of hydrogen atoms in the
hydrocarbon part of the molecule.
For example, for butanoic acid (with functional group -COOH):
• its molecular formula is C4H8O2

• its fully displayed structural formula is • its ball-and-stick model is
• its condensed structural formula is CH3CH2CH2COOH, which can be condensed further to C3H7COOH

The atomic number of carbon is 6. A carbon atom therefore has six electrons and has an
electronic configuration of (2,4) or 1s22s22p2. A carbon atom has four valence electrons and can
therefore form four covalent bonds with other carbon atoms or atoms of other elements,
including hydrogen, oxygen, nitrogen, and the halogens.
For example, in the methane CH4 molecule, the four hydrogen atoms are
arranged in a tetrahedron around the central carbon atom. The angle
between covalent bonds is 109.5°.
Because carbon has four electrons, they can bond with other carbon
atoms in many ways:
• Single bonds can form in which a carbon atom shares one pair of electrons with another carbon
atom. This leaves three other electrons per carbon atom available for bonding with other atoms. For
example, ethane C2H6 has a single bond between the two carbon atoms.
• Double bonds can form in which a carbon atom shares two pairs of electrons with another carbon
atom. This leaves two other electrons per carbon atom available for bonding with other atoms. For
example, ethene C2H4 has a double bond between two carbon atoms.
Organic compounds containing only single bonds between adjacent carbon atoms are known as saturated
compounds, whereas those containing one or more double bonds between adjacent carbon atoms are
unsaturated compounds.
• Unbranched chains of carbon atoms of different lengths can form. For example, butane C4H10 is an
unbranched chain of four carbon atoms with single bonds between adjacent atoms.

• Branched chains of carbon atoms of different lengths can form. For example, methylpropane C 4H10
is a chain of three carbon atoms with the fourth carbon atom branching off from the middle atom of
the chain.
• Rings of carbon atoms can form. For example, cyclohexane C 6H12 is a ring of six carbon atoms.
The ability of carbon atoms to bond covalently with other carbon atoms to form chains and rings of carbon
atoms is known as catenation.
The simplest organic molecules can be thought of as being composed of two Name of Structure of
parts: functional functional group
group
• the hydrocarbon part, composed of only carbon and hydrogen atoms. carbon-carbon
• the functional group(s), composed of a particular atom, group of atoms, single bond
or bond between adjacent carbon atoms such as -OH or -COOH. The
chemical properties of a compound are determined by the reactions of carbon-carbon
double bond
the functional group(s) present.
hydroxyl group
Organic compounds are classified into groups known as homologous series
based on the functional group that they contain. carboxyl group
ester group

HOMOLOGOUS
homologous series SERIES
A homologous series is a group of organic compounds which all possess the same functional group and can
be represented by the same general formula.
For example, the general formula of the alkane series is CnH2n+2.
Each homologous series has the following characteristics:
• All members of the series have the same functional group.

• All members of the series can be represented by the same general formula.
• Each member of the series differs from the preceding or succeeding member by a – CH2 – group
and by relative molecular mass of 14 (since M(CH2) = 14).
• All members of a series possess similar chemical properties. Reactivity decreases as molar mass
increases (i.e., as the number of carbon atoms per molecule increases).
• All members of a series show a gradual change in their physical properties as their molar mass
increases. In general, as molar mass increases, melting point, boiling point, and density increase.
• All members of the series can be prepared by the same general method.
The names of straight chain members of a homologous series consist of two parts.
• The first part is the prefix related to the total number of carbon atoms present in one molecule.
• The second part is based on the homologous series to which the compound belongs and relates to
the functional group present.
number of carbon prefix 5 pent-

atoms 6 hex-
1 meth- 7 hept-
2 eth- 8 oct-
3 prop- 9 non-
4 but- 10 dec-
The four main homologous series are alkanes, alkenes, alcohols/alkanols, and alkanoic/carboxylic acids.

Name of General Functional group Naming Example Fully displayed structural
homologous formula present members of formula and condensed
series the series structural formula
Alkane CnH2n+2 carbon-carbon prefix + ane ethane
single bond
CH3CH3 or C2H6
Alkene CnH2n carbon-carbon prefix + ene ethene

double bond
CH2 = CH2 or C2H4
Alcohol/ CnH2n+1OH hydroxyl group prefix + anol ethanol

alkanol
CH3CH2OH or C2H5OH
Alkanoic CnH2n+1COOH carboxyl group prefix + ethanoic acid

acid/ anoic acid
carboxylic
acid
CH3COOH

Structural isomerism
Many organic compounds have the same molecular formula (i.e., their molecules contain the same number
of atoms of each element) but different structural formulae because their atoms are bonded differently.
These compounds are called structural isomers and this phenomenon is called structural isomerism.
Structural isomerism is a phenomenon in which two or more organic compounds have the same molecular
formula but different structural formulae.
Each different structural isomer has a different name, and, if they contain the same functional group, they
belong to the same homologous series. They have very similar chemical properties, but, because their
atoms are bonded differently, they have different physical properties. If they contain different functional
groups, they belong to different homologous series and have different chemical and physical properties.
Structural isomers of straight chain molecules can be formed in two ways:
• by the chain of carbon atoms becoming branched

Carbon chains can have side branches of one or more carbon atoms.
e.g., pentane C5H12 has three isomers, one of which is the straight chain isomer and two of which are
formed by branching of the carbon chain as shown below:
• by the position of the functional group changing position

The functional group is usually situated at the right-hand end of the molecule. However, the position
of the functional group can change.
e.g., butene C4H8 has two isomers because the position of the carbon-carbon double bond can change
as shown below:

Naming branched chain isomers
The side chains which branch off from the longest chain of carbon atoms are called alkyl groups. These
groups have the general formula CnH2n+1. They are named by adding the suffix ‘-yl’ to the prefix.
The name of a branched chain molecule is made up of three parts:
• the first part indicates the number of the carbon atom to which the side chain is attached
• the second part is the name of the side chain (i.e., the alkyl group)
• the third part is derived from the homologous series to which the compound belongs and the
longest continuous chain of carbon atoms.
Worked examples
> Determine the name of the following branched chain isomer of C5H12.
Find the longest continuous chain of carbon atoms in the structure and number the carbon atoms from the
end closest to the side chain. The side chain is attached to carbon atom number 2. It is an alkyl group with
one carbon atom, and therefore, the methyl group.
The compound has only carbon-carbon single bonds, and therefore belongs to the alkane series. The
longest continuous carbon chain has four carbon atoms in it, and therefore is named butane.
The name of the compound is 2-methylbutane.
> Determine the name of the following branched chain isomer of C6H14.
Side chains are attached to the second and third carbon atoms. The alkyl group is the methyl group – of
which there are two (di). The compound is an alkane with four carbon atoms in its longest continuous carbon
chain.
This compound is 2,3-dimethylbutane.


OF A
Which of the following is the fully displayed structural The fully displayed structures for two hydrocarbons,
formula of 2-bromobutane? Compound A and Compound B, are shown below.
(A)
(B) (i) Name the homologous series to which Compounds

A and B belong.
(C) (ii) State the name of EACH compound.

(iii) Define ‘structural isomerism’.
(iv) Draw the FULLY DISPLAYED structure of ONE
structural isomer for EACH of Compounds A and B.
(D)
The answer is (C). i/A to the alkanes, B to the alkenes
2020 CSEC Chemistry Paper 01 ii/A is 2-methylbutane and B is 2-butene (or but-2-ene)
Note: ‘butene’ alone is insufficient.
Which of the following about ethane is correct?
iii/Structural isomerism is the existence of organic
compounds with the same molecular formula but
(A) Structural formula different structural formulae
(B) Molecular formula – C2H4
iv/
(C) Empirical formula – CH2
(D) General formula – CnH2n+2 A:
The answer is (D) General formula – CnH2n+2. All other

options describe ethene.

2,2-dimethylpropane pentane
Compounds in a homologous series
B:
(A) exist in the same state
(B) possess the same molecular formula
(C) differ successively by a −CH2 group
(D) possess only carbon in straight chains
The answer is (C).


2020 CSEC Chemistry Paper 01 2010 CSEC Chemistry Paper 02
This item refers to the fully displayed structural formulae of The structures of four hydrocarbons, a, b, c, and d are
compounds Q, R, and S shown below. shown below.
Which of the following correctly identifies the homologous

series to which each compound belongs?
Q R S
(A) Ester Acid Alcohol
(B) Acid Alcohol Ester (i) Give the name for structure a. (1 mk)
(C) Alcohol Ester Acid (ii) State which of these hydrocarbons are isomers.
(D) Acid Ester Alcohol (2 mks)
(iii) Which TWO hydrocarbons belong to the same
The answer is (D).
homologous series? Give ONE reason for your answer.
2004 CSEC Chemistry Paper 01 (2 mks)
(iv) Write the general formula of the isomers identified in
A compound was found to have a molecular formula C 4H6.
(iii) above. (1 mk)
Which of the following is NOT an isomer of this compound?
i/2-methylprop-1-ene
ii/a, b, and c
(A) iii/a and b (alkenes) – both have a carbon-carbon double

bond present
(B)
iv/CnH2n
(C)
(D)
The answer is (C). The molecular formula of compounds (A),
(B), and (D) are C4H6, whereas that of (C) is C4H8.
3. Reactions of Carbon Compounds

The following diagram shows how apparatus and materials Ethanol reacts with different reagents to form products
are used to identify the products formed when ethanol with the functional groups shown in the table below.
burns. Complete the table by identifying the reagents or
reaction conditions and drawing the fully displayed
structures of the products.
Which of the following BEST describes what will be observed

in the U-tube and the test tube at the end of the
investigation?
U-tube Test-tube
(A) Colourless liquid Carbon dioxide
(B) Water White precipitate Typical Exam Question / 2011 CSEC Chemistry Paper 02
(C) Colourless liquid White precipitate
Compound A (C3H6) and Compound B (C3H8) are
(D) Water Carbon dioxide
hydrocarbons.
Typical Exam Question / 2018 CSEC Chemistry Paper 01 One of these compounds reacts with bromine dissolved
If the ice were removed, which of the following would
in trichloroethane.
The fermentation
represent of sugars,
the equation using
for the glucose as the substrate,
reaction?
can be represented by the equation (i) State the observation for this reaction. (1 mk)
(A)
(ii) Write a chemical equation for this reaction.
(A)
(B) C6H12O6 + 6O2 → 6CO2 + 6H2O
(1 mk)
(B)
(C) C6H12O6 + C6H12O6 → C12H22O11 + H2O
(iii) Draw the FULLY displayed structure of the
(C)
(D) C6H12O6 → 2C2H5OH + 2CO2
product in the equation in Part ii) above and state
(D) 6CO2 + 6H2O → C6H12O6 + 6O2
the name of this product. (2 mks)
• describe the reactions of alkanes and alkenes;

o The chemical reactions considered should be: burning and halogenation of alkanes and
alkenes; hydration and hydrogenation for alkenes. Equations and conditions for equations
are required.

• relate the characteristic reactions of alkanes and alkenes to their structures;
o Emphasis should be placed on the dominance of substitution in alkanes and addition in
alkenes.
• distinguish between alkanes and alkenes;
o Carbon-Carbon double bond (C=C) associated with unsaturation.
• relate the properties of hydrocarbons to their uses;
o Alkanes as fuels and solvents and alkenes as the starting material for a wide range of
polymers (for example, plastics), biogas production from decomposition of manure.
o Refer to SO B4.2.
• identify alcohols, acids, and esters by their functional groups;
o Alcohol: R−OH, Acid: R−COOH, Ester: COO−R where R represents an alkyl group.
• relate the properties of alcohols, acids, and esters to their functional groups;
o The presence of hydroxyl (−OH) groups linked to solubility and volatility.
• describe the reactions of ethanol;
o Combustion, reaction with sodium, dehydration. Oxidation by reaction with potassium
dichromate (VI), KMnO4. Reaction with organic acids to form esters. Equations and conditions
for reactions are required. Equations for the conversion to acid are not required.
o Refer to SO A8.5.
• describe the fermentation process by which ethanol is produced from carbohydrates;
o Fermentation of a suitable carbohydrate, for example, glucose. Equation is required.
Reference to wine-making and rum manufacture.
o Draw line diagrams of the distillation process in the laboratory.
o Refer to SOA2.5.
• describe the reactions of ethanoic acid;
o Condensation reactions with alcohols (ester formation). Reactions with metals, oxides,
hydroxides, and carbonates. Equations and conditions of reactions are required.
• explain hydrolysis of esters including saponification;
o Equation for hydrolysis of an ester.
o Include saponification of fats and oils.
• compare soapy and soapless detergents;
o Compare effect on hard and soft water, environmental impact.
o Refer to SO C5.5, C5.6, C5.7.

ORGANICorganic
CHEMISTRY
chemistry reactions REACTIONS
Alkanes
Alkanes are a group of colourless, saturated hydrocarbons (containing only carbon-carbon single bonds)
which are generally unreactive. However, alkanes do undergo combustion reactions, can react with halogens
in the presence of light, and can be cracked into smaller molecules (see B1. Sources of Hydrocarbons).
Combustion
Alkanes burn very easily in air or oxygen. The complete combustion of an alkane (when the oxygen supply is
plentiful) produces carbon dioxide and steam, whereas the products of the incomplete combustion are
carbon monoxide and steam.
The complete combustion of methane is:
CH4(g) + 2O2(g) → CO2(g) + 2H2O(g)
Alkanes burn with clear, blue, non-smoky flames because they have a low ratio of carbon to hydrogen
atoms in their molecules – all carbon is converted to carbon dioxide or carbon monoxide.
The combustion of methane
The incomplete combustion of methane is:
2CH4(g) + 3O2(g) → 2CO(g) + 4H2O(g)
In this incomplete combustion, some carbon may remain unreacted. The flame produced can be yellow and
smoky as unreacted carbon remains in the flames..
This combustion reaction is exothermic and produces large amounts of heat energy, making alkanes useful
fuels.

Halogenation
Alkanes undergo a substitution reaction (= reaction in which one atom or group of atoms is swapped with
another) with halogens in the presence of light (ultraviolet light works best but sunlight is often sufficient),
forming halogenoalkanes/haloalkanes/alkyl halides.
A substitution reaction takes place in stages, and its speed depends on light intensity (the brighter the light,
the faster the reaction) and the reactivity of both the halogen and the alkane (fluorine has the most rapid
reaction whereas iodine does not react with alkanes at all; methane has the most rapid reaction because it is
the smallest alkane molecule).
For example, methane reacts with chlorine in the presence of light to form chloromethane (a
halogenoalkane) and hydrogen chloride. In bright light, the reaction is rapid, whereas in dim light, a slow
substitution reaction occurs in stages, with one hydrogen atom being replaced by one chlorine atom at a
time.
i.e.,
CH4(g) + Cl2(g)→CH3Cl(g) + HCl(g)
As the reaction continues, the hydrogen atoms are replaced one by one until tetrachloromethane is
produced:
CH3Cl(g) + Cl2(g)→CH2Cl2(l) + HCl(g)
CH2Cl2(l) + Cl2(g)→CHCl3(l) + HCl(g)
CHCl3(g) + Cl2(g)→CCl4(l) + HCl(g)
The overall reaction can be summarised by:

𝑈𝑉 𝑙𝑖𝑔ℎ𝑡
CH4(g) + 4Cl2(g) → CCl4(l) + 4HCl(g)
Methane has a similar reaction with bromine vapour or bromine solution, but slower (since bromine is less
reactive than chlorine). During the reaction between bromine and an alkane, the colour of bromine slowly
fades from red-brown to colourless.

Alkanes are used mainly as fuels and solvents.
Use as fuels Use as solvents

Alkanes burn easily when ignited, releasing a Alkanes are non-polar molecules and so
large amount of energy (exothermic reaction). dissolve a variety of other non-polar solutes. For
They also burn with a clear, blue flame with a example, hexane and heptane are used as
very low soot content (i.e., they are clean solvents in manufacturing fast-drying glues and
burning fuels), and they are stored easily as extracting oils from seeds. Petroleum jelly is oil
liquids in containers, making them to store, dissolved in paraffin wax (a solid alkane).
transport and distribute.
Biogas production
Biogas, a renewable energy source, is produced by naturally occurring anaerobic bacteria breaking down
organic matter (e.g., manure, food waste) in the absence of oxygen in a sealed anaerobic digester.
It is a mixture of about 60% methane, 40% carbon dioxide, and traces of contaminant gases such as
hydrogen sulphide.
Biogas can be used directly as a fuel for cooking, heating, and electricity generation, or other gases removed
from it, and it being upgraded to almost pure methane, known as biomethane. This biomethane can be
piped to homes with natural gas or liquefied under pressure to produced liquefied natural gas (LNG) for use
in certain vehicles.
The leftover indigestible material and dead organisms (called digestate) can then be used as a fertiliser.
Biogas production reduces demand on fossil fuels, recycles soil nutrients, and reduces waste going to
landfills.

Alkenes
Alkenes are a group of unsaturated hydrocarbons (containing carbon-carbon double bonds). Because of
these double bonds, alkenes are much more reactive than alkanes – the double bond means they can
make more bonds with other atoms by opening up the C = C bond and allowing incoming atoms to form
another single bond with each carbon atom of the functional group.
Alkenes undergo a variety of reactions, two of which are combustion and addition reactions.
Combustion
Similar to alkanes, alkenes burn very easily in air or oxygen. Further, the complete combustion of an alkene
also produces carbon dioxide and steam. However, alkanes require more oxygen for complete combustion
than the corresponding alkane with the same number of carbon since alkenes have a higher ratio of carbon
atoms to hydrogen atoms. Because of this high ratio, alkenes do not burn with clean flames – they release
unreacted carbon as soot. They also burn with a smoky flame.
The complete combustion of ethene is:
C2H4(g) + 3O2(g) → 2CO2(g) + 2H2O(g)
Addition
Alkenes undergo addition reactions with other small molecules. In these

reactions, the alkene and the other molecule react to form a single molecule. One
bond in the double bond is broken, and the compound formed is saturated.
It is important to know some specific addition reactions that alkenes undergo.
Hydrogenation
Alkenes undergo addition reactions with hydrogen gas to produce an alkane. This reaction is called
hydrogenation. The single bond between the hydrogen atoms in the hydrogen molecule breaks, and one
atom is bonded to each carbon atom at either side of the original double bond. For the reaction to take
place, a pressure of about 5 atm, and a temperature of about 150degC, and a nickel catalyst are required.
For example, ethene reacts with hydrogen to form ethane under these conditions.
i.e.,

Halogenation
As with alkanes, alkenes undergo halogenation reactions. However, alkanes undergo substitution reactions,
whereas alkenes undergo addition reactions. Alkenes do not require light energy to take place, and the
reaction is very rapid. During halogenation an alkene undergoes, the single bond between the halogen
atoms in the molecule breaks, and one atom is bonded to each carbon atom at either side of the original
double bond. A halogenoalkane is produced from this reaction.
For example, propene reacts with bromine (vapour or solution) to form 1,2-dibromopropane.
i.e.,
C3H6(g) + Br2(g) → C3H6Br2(l)
The red-brown bromine is rapidly decolourised.
Alkenes also undergo addition reactions with hydrogen halides such as HCl and HBr at room temperature to
form halogenoalkanes.
For example, ethene reacts with hydrogen chloride to form monochloroethane:
i.e.,
C2H4(g) + HCl(g) → C2H5Cl(l)


Hydration
Alkenes undergo addition reactions with steam to produce an alcohol. This reaction is called hydration. One
of the bonds between a hydrogen atom and the oxygen atom in the water molecule breaks, and the
hydrogen atom is bonded to the carbon atom at one side of the original double bond, and the remaining OH
group is bonded to the carbon atom at the other side. For the reaction to take place, a pressure of 60-70
atm, a temperature of about 300degC, and a catalyst of phosphoric acid in sand (silica) are required.
For example, ethene reacts with steam to form ethanol.
i.e.,
𝐻3 𝑃𝑂4 𝑐𝑎𝑡𝑎𝑙𝑦𝑠𝑡, 70 𝑎𝑡𝑚, 300℃

C2H4(g) + H2O(g) → C2H5OH(l)
Ethanol is produced industrially by this reaction. The yield is very low, so the unreacted ethene is recycled
back into the reaction vessel to increase the yield.
Addition reaction with acidified potassium manganate(VII)
Alkenes undergo addition reactions with acidified potassium manganate(VII) solution to form a diol (= an
alcohol with two −OH groups).
For example, ethene reacts with acidified potassium manganate(VII) to form ethane-1,2-diol.
i.e.,
C2H4(g) + H2O(l) → C2H4(OH)2(l)
The purple acidified potassium manganate(VII) is rapidly changes from purple to colourless as the alkene
reduces the purple MnO4- ion to the colourless Mn2+ ion (i.e., the alkene acts as a reducing agent).

Uses of alkenes
Alkenes are important starting materials for the manufacture of many chemicals because of their ability to
undergo addition reactions (since they are unsaturated). For example, they are used to manufacture ethanol
and other alcohols in halogenation reactions as well as antifreezes (such as ethane-1,2-diol) and synthetic
rubbers. Alkenes can also undergo addition reactions with themselves, where they are used to make
polymers or plastics (see B4. Polymers).
Distinguishing between an alkane and an alkene
The reaction when an alkane and an alkene react with bromine solution or acidified potassium
manganate(VII) solution is very different, and used to distinguish between the two. These reactions test to
see if the compound is unsaturated (i.e., it contains a carbon-carbon double bond).
Observation and explanation

Test
Alkane Alkene
The solution remains red-brown. The solution rapidly changes
colour from red-brown to
No reaction occurs (under colourless.
Add bromine solution (bromine
standard laboratory conditions).
dissolved in water or in
A rapid addition reaction occurs,
tetrachloromethane) under
In UV light, the solution will which forms a colourless
standard laboratory conditions
slowly change from red-brown haloalkane.
to colourless due to the slow
substitution reaction occurring.
The solution remains purple. The solution rapidly changes
colour from purple to colourless.
No reaction occurs.
Add acidified potassium
A rapid addition reaction occurs,
manganate(VII) solution
during which the alkene reduces
the H+/KMnO4.

Alcohols
Alcohols or alkanols have the hydroxyl group and follow the general formula CnH2n+1OH (or R−OH, R
representing an alkyl group).
2-hexanol, an alcohol
Alcohol molecules are polar (have regions of positive and negative charge, see A5. Structure and Bonding)
because they have the polar −OH group. Because they are polar:
• they are less volatile than their corresponding alkanes with the same number of carbon atoms (i.e.,
their boiling point is higher than the alkane). The polar −OH groups cause the forces of attraction
between the alcohol molecules to be stronger than between the non-polar molecules. For example,
the boiling point of ethanol is 78degC whereas that of ethane is −89degC. Further, all alcohols are
liquid or solid at room temperature. Note that as the number of carbon atoms in an alcohol
increases, the intermolecular forces between the molecules increases, making the boiling point
increase.
• they are soluble in water, as polar solutes dissolve inn polar solvents (of which water is one). Small
alcohols such as methanol, ethanol, and propanol are completely soluble in water, however,
solubility decreases as the number of carbon atoms in the alcohol increases.
Alcohols undergo various reactions due to the presence of the hydroxyl group. The reactions described
below are of ethanol, however, the other alcohols undergo similar reactions. Note that the strength of the
reactions decreases as the number of carbon atoms in the alcohol increases.
Combustion
Ethanol burns very easily in air or oxygen, producing carbon dioxide and steam.
C2H5OH(l) + 3O2(g) → 2CO2(g) + 3H2O(g)
Similar to an alkane, ethanol burns with a clear blue flame due to the low ratio of carbon atoms to hydrogen
atoms – no unreacted carbon remains to produce soot.

Reaction with sodium
Ethanol reacts with sodium, producing a colourless solution of sodium ethoxide C2H5ONa
in alcohol (called an alcohol solution –alc sol) and hydrogen.
i.e.,
Fully displayed structure of
2C2H5OH(l) + 2Na(s) → 2C2H5ONa(alc sol) + H2(g) sodium ethoxide
Dehydration
Ethanol can be dehydrated (= removing a water molecule (i.e., the hydroxide group and a hydrogen atom
removed)) to ethene in two ways:
• mixing it with excess concentrated sulphuric acid (catalyst) and heating the mixture to 170degC
𝑐𝑜𝑛𝑐𝑒𝑛𝑡𝑟𝑎𝑡𝑒𝑑 𝐻2 𝑆𝑂4 , 170℃

C2H5OH(l) → C2H4(g) + H2O(l)
• passing ethanol vapour over aluminium oxide at 350degC (catalyst)
𝐴𝑙2 𝑂3 , 450℃
C2H5OH(g) → C2H4(g) + H2O(l)
Oxidation
Ethanol is oxidised to ethanoic acid when heated with a powerful oxidising agent such as acidified potassium
manganate(VII) solution or acidified potassium dichromate(VI) solution.
C2H5OH(l) + 2[O] → CH3COOH(aq) + H2(g)
Ethanol acts as a reducing agent, reducing the purple MnO4- ion to the colourless Mn2+ ion or reducing the
orange Cr2O72- ion to the green Cr3+ ion.
This principle is used in the breathalyser test, testing the alcohol content of a driver’s breath. The driver
blows over a sample of orange acidified potassium dichromate(VI) crystals, which will turn green if the
driver’s breath contains ethanol vapour.
Reaction with carboxylic acid
Ethanol reacts with a carboxylic acid to form an ester and water. This is explained later.

Production of ethanol by fermentation
Ethanol is the type of alcohol found in alcoholic drinks such as wine and beer, making it commercially
important. Ethanol can be produced by fermentation – the chemical reaction by which starch is converted
into ethanol by yeast (a unicellular fungus) under anaerobic conditions. Yeast produces enzymes in order to
break down complex carbohydrates into simple sugars (mainly glucose), then produces zymase that converts
the simple sugars into ethanol and carbon dioxide.
i.e.,
𝑧𝑦𝑚𝑎𝑠𝑒 𝑖𝑛 𝑦𝑒𝑎𝑠𝑡
C6H12O6(aq) → 2C2H5OH(aq) + 2CO2 ∆𝐻 − 𝑣𝑒
This reaction is exothermic and provides energy to yeast cells. For it to occur, the temperature must be
between about 15degC and 35degC for the enzymes to function. Further, the reaction mixture must have a
pH value near 7, water must be present, and oxygen must be absent.
Production of ethanol by fermentation
When the concentration of ethanol in the fermentation mixture reaches about 14%, it becomes to destroy the
zymase and fermentation stops. The ethanol is then separated from the mixture by fractional distillation (see
A2. Mixtures and Separations) – the product is collected at 78degC and is about 96% pure.
Separation of ethanol by fractional distillation


Winemaking
Wine is mainly made from grapes in a winery. The grapes are crushed, forming a mixture of pulp, skins, and
juice known as must. A vintner (winemaker) then adds yeast to the must in fermentation tanks and they
ferment the sugars present. When fermentation process is complete, the skins are removed and the wine is
clarified by filtration. The win is then aged in tanks or barrels before bottling.
The exposure to air during the winemaking process must be minimised so that aerobic bacteria do not oxidise
the ethanol to ethanoic acid, making the wine sour and undrinkable.
i.e.,
𝑎𝑒𝑟𝑜𝑏𝑖𝑐 𝑏𝑎𝑐𝑡𝑒𝑟𝑖𝑎
C2H5OH(aq) + O2(g) → CH3COOH(aq) + H2O(l)
Rum manufacture
The extraction of sugar from sugar cane (see A2. Mixtures and Separation) produces a black treacle-like
substance known as molasses, from which rum is made. The molasses is diluted with water and yeast is
added to the mixture. The yeast ferments the molasses to ethanol and carbon dioxide. After 48 hours of
fermentation, the liquid is distilled (simply or fractionally). The distillate from fractional distillation contains
96% ethanol, which is diluted with water in put in oak barrels to age – a process which can take twenty years
or more.
Making ethanol for industrial use by fermentation has some advantages and disadvantages compared with
making ethanol by hydration of ethene.
• Fermentation requires distillation and the ethanol produced still contains some water, whereas
ethanol produced by hydration is relatively pure.
• The rate of reaction for fermentation is slow but fast for hydration.
• Ethanol by fermentation can only be made in batches, whereas hydration enables continuous
production.
• Fermentation is simple and uses renewable resources, whereas hydration is complex, expensive, and
uses non-renewable resources.

Carboxylic acids
Carboxylic or alkanoic acids have the carboxyl group and follow the general formula CnH2n+1COOH (or R−COOH).
Butanoic acid, a carboxylic acid
Like alcohols, carboxylic acid molecules are polar because the polar −OH is present in the carboxyl group. The
properties of carboxylic acids are related to their polar nature:
• they are less volatile than their corresponding alkanes with the same number of carbon atoms (i.e.,
their boiling point is higher than the alkane). The forces of attraction between the polar carboxylic acid
molecules are stronger than that between the non-polar molecules. For example, the boiling point of
ethanoic acid is 112degC whereas that of ethane is -89degC. Further, all carboxylic acids are liquid or
solid at room temperature. Note that as the number of carbon atoms in a carboxylic acid increases,
the intermolecular forces between the molecules increases, making the boiling point increase.
• they are soluble in water, as polar solutes dissolve inn polar solvents (of which water is one). Small
carboxylic acids such as methanoic acid, ethanoic acid, and propanoic acid are completely soluble in
water, however, solubility decreases as the number of carbon atoms in the carboxylic acid increases.
When carboxylic acids dissolve in water, the ionise to a very small degree to form hydrogen ions,
making them weak acids. When ethanoic acid dissolves in water, only 1% of the ethanoic acid
molecules ionise. (leaving 99% ethanoic acid molecules).
i.e.,
CH3COOH(aq) ⇌ H+(aq) + CH3COO-(aq)
Aqueous solutions of carboxylic acids react similarly to inorganic acids when reacted with reactive metals,
metal oxides, metal hydroxides, and metal carbonates. However, the reactions are slower because carboxylic
acids are weak acids.
Carboxylic acids undergo various reactions due to the presence of the carboxyl group. The reactions described
hereinafter are of ethanoic acid, however, the other carboxylic undergo similar reactions. Note that the
strength of the reactions decreases as the number of carbon atoms in the carboxylic acid increases.

Reaction with reactive metals
When ethanoic acid is reacted with a reactive metal, a salt (an ethanoate) and hydrogen gas are produced.
e.g.,
Mg(s) + 2CH3COOH(aq) → (CH3COO)2Mg(aq) + H2(g)
Reaction with metal oxides
When ethanoic acid is reacted with a metal oxide, a neutralisation occurs (as metal oxides are basic). An
ethanoate and water are produced.
e.g.,
Fe2O3(s) + 6CH3COOH(aq) → 2(CH3COO)3Fe(aq) + 3H2O(l)
Reaction with metal carbonates
When ethanoic acid is reacted with a metal carbonate, an ethanoate, carbon dioxide, and water are produced.
e.g.,
CaCO3(s) + 2CH3COOH(aq) → (CH3COO)2Ca(aq) + CO2(g) + H2O(l)
Esterification
Esterification is the process of combining an organic acid (RCOOH) with an alcohol (ROH) to form an ester
(RCOOR) and water. This reaction is reversible and requires heat and concentration sulphuric acid as a catalyst
to occur. During the reaction, a water molecule is lost between the reactants. This means that esterification is
a condensation reaction. Note that for esterification to occur, the carboxylic acid and alcohol must be in pure
liquid form, not in aqueous solution.
For example, ethanoic acid and propanol react (in the presence of the concentrated H 2SO4 catalyst and heat)
to form propyl ethanoate (an ester) and water.
i.e.,
Concentrated sulphuric acid is needed as a catalyst to speed up the reaction. It is also a powerful dehydrating
agent, which removes the water produced during the reaction (which favours the forward reaction) and
increases the yield.

Esters
Esters have the ester group −COO− and follow the general formula CnH2n+1COOCxH2x+1 (or
R−COO−R’). (n and x may be the same or different numbers; R and R’ may be the same or
different alkyl groups.)
The ester group
Esters are made by a condensation reaction known as esterification as previously described.
𝑐𝑜𝑛𝑐. 𝐻2 𝑆𝑂4
carboxylic acid + alcohol ⇌ ester + water
ℎ𝑒𝑎𝑡
In naming esters, the alcohol forms the first part (ending with -yl), and the acid part forms the second part
(ending with -anoate).
In the reaction between ethanoic acid and ethanol:
In naming esters, the alcohol forms the first part (ending with -yl), and the acid part forms the second part
(ending with -anoate). For example, butanoic acid and methanol react to form methyl butanoate.
Hydrolysis
In a hydrolysis reaction, molecules are broken down into smaller ones by reacting with water. Esters can be
hydrolysed by heating with a dilute acid or an aqueous alkali.
• Acid hydrolysis
When an ester is heated with an acid catalyst, a carboxylic acid and an alcohol are produced.

• Alkaline hydrolysis
When an ester is heated with sodium or potassium hydroxide solution, the sodium or potassium salt
of a carboxylic acid and an alcohol are produced. The reaction occurs in two stages: the formation of
the carboxylic acid and the alcohol, then the neutralisation of the acid by the alkali.
For example, in the alkaline hydrolysis of ethyl ethanoate by reacting it with sodium hydroxide
solution:
Stage 1: The ethyl ethanoate reacts with water in the presence of OH- ions to form ethanoic acid and
ethanol.
Stage 2: The ethanoic acid is neutralised by the sodium hydroxide solution to form sodium ethanoate.
The overall reaction is:

CH3COOC2H5(l) + NaOH(aq) → CH3COONa(aq) + C2H5OH(aq)
Saponification
Saponification refers to the process that produces soap – large ester molecules found in animal fats and
vegetable oils undergo alkaline hydrolysis by being boiled with concentrated potassium or sodium hydroxide
solution. The soap produced in the reaction is the potassium or sodium salt of a long chain carboxylic acid
(known as fatty acids) as well as glycerol C3H5(OH)3. Glycerol is a triol – it has three hydroxyl functional
groups.
ℎ𝑒𝑎𝑡
fat or oil + NaOH → sodium salt of a long-chain carboxylic acid + glycerol

For example, glyceryl octadecanoate (C17H35COO)3C3H5 is an ester of the fatty acid known as octadecanoic acid
and glycerol. When glyceryl octadecanoate is hydrolysed by boiling with concentrated sodium hydroxide
solution, sodium octadecanoate C17H35COONa (a form of soap) and glycerol are produced.
i.e.,
A soap molecule
When the soap has been produced, the mixture is added to saturated sodium chloride solution to precipitate
out and solidify the soap.
Suction filtration is used to separate soap from the reaction mixture


Detergent
Detergents are chemicals added to water to remove dirt (from skin, clothes, surfaces, etc.). Detergent
molecules are composed of long molecules with two ends: an ionic head (ionic, and readily dissolves in water
making it hydrophilic) and a hydrocarbon tail (covalent, and readily dissolves in organic substances such as oil
and grease making it hydrophobic).
Detergent molecule
Dirt often consists of oily or greasy substances that do not dissolve in water, making them difficult to remove.
Detergents lower the surface tension of the water, loosening the dirt molecules and dispersing them in the
water (they help to make the greasy dirt mix with the water).
When a detergent is added to oily or greasy dirt, the hydrophobic tail dissolves in the greasy dirt and the
hydrophilic head sticks out – the head dissolves in water and the dirt is lifted from fabric or skin and is
washed away.

There are two types of detergents:
• Soapy detergents (or simply soaps) are made by boiling animal vats or vegetable oils with
concentrated potassium or sodium hydroxide solution, for example, sodium octadecanoate. These do
not lather easily in hard water (which contains dissolved calcium and magnesium salts; see C5. Non-
metals) – the calcium and magnesium ions displace the sodium ions in the soap forming an insoluble
precipitate of calcium or magnesium octadecanoate known as scum.
Scum removes the soap from the solution, preventing it from removing greasy dirt. It is only when all
the calcium and magnesium ions have been precipitated out that any remaining soap molecules will
form a lather and remove the dirt.
• Soapless or synthetic detergents (or simply detergents) are formed from petroleum, for example,
sodium dodecyl sulphate C12H25OSO3Na. They lather much more easily with hard water than soapy
detergents because their calcium and magnesium salts are soluble (therefore, they do not form
scum).
Soapy detergents Soapless detergents

Manufactured from fats and oils (renewable) Manufactured from petroleum (non-renewable)
Do not lather easily in hard water and form scum Lather in hard water because their calcium and
which wastes soaps, discolours clothes, and magnesium salts are soluble
forms an unpleasant greasy layer around sinks
and baths
Are biodegradable (= can be broken down by Some are non-biodegradable, causing foam to
bacteria in the environment) so do not cause build up in sewage system which kills aquatic
foaming in sewage systems or on waterways organisms (oxygen can no longer dissolve in the
water) and makes sewage treatment difficult.
Most modern ones are biodegradable.
Do not contain phosphates so do not cause Some contain phosphates (added to improve
eutrophication of aquatic environments cleaning ability) which cause eutrophication (=
nutrient enrichment stimulating the rapid growth
of green algae)

OF A
The following diagram shows how apparatus and materials Ethanol reacts with different reagents to form products
are used to identify the products formed when ethanol with the functional groups shown in the table below.
burns. Complete the table by identifying the reagents or
reaction conditions and drawing the fully displayed
structures of the products.
Conc. H2SO4
170degC
Which of the following BEST describes what will be observed

in the U-tube and the test tube at the end of the H+/KMnO4
or H+/K2Cr2O7
investigation?
U-tube Test-tube
Carboxylic acid
(e.g., CH3COOH)
Conc. H2SO4
(A) Colourless liquid Carbon dioxide
(B) Water White precipitate
(C) Colourless liquid White precipitate Typical Exam Question / 2011 CSEC Chemistry Paper 02
(D) Water Carbon dioxide
Compound A (C3H6) and Compound B (C3H8) are
hydrocarbons.
The answer is (C). The combustion of ethanol produces
water (a colourless liquid) and carbon dioxide (which forms a One of these compounds reacts with bromine dissolved
white precipitate when fixed with aqueous Ca(OH)2). in trichloroethane.
If the ice were removed, which of the following would (i) State the observation for this reaction. (1 mk)
represent the equation for the reaction? (ii) Write a chemical equation for this reaction. (1 mk)
(iii) Draw the FULLY displayed structure of the product
(A) 2C2H5OH(aq) + 7O2(g) → 4CO2(g) + 6H2O(l) in the equation in Part ii) above and state the
(B) 2C2H5OH(l) + 7O2(g) → 4CO2(g) + 6H2O(g) name of this product. (2 mks)
(C) 2C2H5OH(aq) + 7O2(g) → 4CO2(g) + 6H2O(aq)
(D) 2C2H5OH(aq) + 7O2(g) → 4CO2(g) + 6H2O(g) i/The colour of the solution changes from brown to
colourless
The answer is (B).
ii/ C3H6(g) + Br2(aq) → C3G6Br2(l)
iii/
1,2-dibromopropane

Typical Exam Question / 2018 CSEC Chemistry Paper 01 2017 CSEC Chemistry Paper 02
The fermentation of sugars, using glucose as the substrate, Compound Q has the condensed molecular formula
can be represented by the equation CH3CH2COOH.
(A) C6H12O6 + 6O2 → 6CO2 + 6H2O (i) Explain why Compound Q is soluble in water. (2 mks)
(B) C6H12O6 + C6H12O6 → C12H22O11 + H2O (ii) Is the solution of Compound Q acidic or basic? State a
(C) C6H12O6 → 2C2H5OH + 2CO2 reason for your answer. (2 mks)
(D) 6CO2 + 6H2O → C6H12O6 + 6O2
i/The −OH group in Compound Q makes it polar. Since
The answer is (C) C6H12O6 → 2C2H5OH + 2CO2. water is a polar solvent and like dissolves like, Compound
Q is soluble in water.
ii/The solution of Compound Q is acidic. When Compound
Which of the following structures represents a compound
Q dissolves in water, a low amount of hydrogen ions H+ per
that can react with an alcohol to produce a sweet smelling
unit volume. Since it releases hydrogen ions in solution, it
liquid?
is an acid.

(A)
State the conditions required for the dehydration of
ethanol. (2 mks)
(B)
Either (i) a temperature of 170degC with concentrated
H2SO4/H3PO4 as a catalyst or (ii) activated alumina Al2O3
(C)
and 450degC.

(D)
The figure below shows Compound A and B which are from
The answer is (C). Carboxylic acids react with alcohols to
different homologous series.
produce ester, which are sweet-smelling.
Which reaction involves the boiling of a fat or oil with

aqueous sodium hydroxide (caustic soda)?
(A) Hydrolysis State whether Compound A will undergo a condensation

(B) Dehydration reaction or addition polymerisation reaction with alcohols.
(C) Saponification (1 mk)
(D) Esterification Compound A is a carboxylic acid, and so will undergo a
The answer is (C) Saponification. condensation reaction with alcohols (to produce an ester).
4. Polymers
Nylon is a macromolecule which is held together by the The molecule shown below can be used to produce
same linkage as a protein molecule. What is the name given polymers which are very useful in industry.
to this type of linkage?
(A) Amide bond

(B) Double bond
(C) Ester linkage A partial structure of the polymer is shown below.
(D) Ether linkage
Glucose is converted to starch or cellulose by (i) Name the functional group (link) present in the
polymer. (1 mk)
(A) condensation polymerisation
(ii) Name the type of polymerisation reaction that
(B) addition polymerisation
has taken place, and state ONE possible use of
(C) oxidation and reduction
these types of polymers. (2 mks)
(D) dehydrogenation
(iii) Name the by-product that is formed in this
polymerisation reaction. (1 mk)
• define polymers;
o Polymers as macromolecules produced from 50 or more monomers.
• distinguish between addition and condensation as reactions in the formation of polymers;
o Addition – polyalkenes; condensation – polyamines, polyesters, polysaccharides. The
mechanism of polymerisation is NOT required.
o Refer to SO B3.4.
• state at least one use of each of the following types of polymers.
o Polyalkene, polyamide, polyester, polysaccharide. A named example is required in each case,
for example, polyvinyl chloride (PVC) used in pipe fittings.
o Refer to SO C5.5.
4. Polymers
POLYMERS
polymers
Polymers are macromolecules built by linking 50 or more smaller molecules called monomers. Each repeat
unit in a polymer is connected to the adjacent units via covalent bonds.
Some polymers contain just one type of unit such as poly(ethene) and poly(chloroethene), whereas others
contain two or more different types of monomer units (copolymers) such as nylon and biological proteins.
The reaction by which a polymer is formed from a monomer is known as polymerisation. There are two
types of polymerisation: addition and condensation.
Addition polymerisation
Addition polymerisation occurs when unsaturated monomers (that contain C=C bonds) such as alkenes are
linked together, forming a saturated polymer (the only product) known as an addition polymer. For addition
polymerisation to occur, one of the bonds in the C=C double bond of each monomer breaks and forms a
single covalent bond with an adjacent monomer. The monomers which make the polymer must all be the
same, and the empirical formula of the polymer is the same as the monomer that formed it.
Addition polymers are synthetic, i.e., they are man-made. The conditions required to make most addition
polymers are high pressure, heat, and a catalyst.
Polyalkenes
Addition polymers produced from alkenes by addition polymerisation are polyalkenes. They are saturated
compounds because they only have single bonds between carbon atoms. The carbon-carbon single bond
linking each monomer unit together is known as an alkane linkage.
Poly(ethene)
When ethene C2H4 is placed in a pressurised container and heated it with a catalyst, poly(ethene) is formed.
one of the bonds in the double bond of each molecule breaks and poly(ethene) is formed.
4. Polymers
Poly(propene)
When propene C3H6 is placed in a pressurised container and heated with a catalyst, poly(propene) is formed.
If the monomer in addition polymerisation contains other atoms, the groups of atoms or functional groups
can be represented as follows:
Uses of addition polymers
Name of Chemical name of Structure of Common Uses

monomer polymer polymer name of
polymer
ethene poly(ethene) polythene Manufacture of plastic bags,
plastic bottles, sandwich bags,
cling wrap, packaging materials,
and moisture barriers
propene poly(propene) polypropene Manufacture of ropes, plastic
toys, carpets, and plastic food
containers
chloroethene poly(chloroethene) polyvinyl Manufacture of pipe fittings,
chloride guttering, plastic windows, and
(PVC) insulation for cables
tetra- poly(tetrafluoroethene) Teflon® As a non-stick coating on kitchen

fluoroethene and garden utensils;
manufacture of low-friction
bearings
phenylethane/ poly(phenylethene) polystyrene Manufacture of fast-food
styrene containers and vending cups for
drinks; protective packing
material; insulation material in
walls and roofs
4. Polymers
Condensation polymerisation
Condensation polymerisation occurs when monomers (which may be different) are linked together with the
removal of a small molecule (usually, but not always, water). Hence, in addition to the condensation
polymer, the small molecule is also formed as a product per linkage (two products are always formed). The
monomers have two functional groups present – one on each end. These functional groups react, creating
long chains of alternating monomers. The empirical formula of the polymer is different from the monomer
since atoms are lost during the formation of the polymer.
When the small molecule is water, one hydrogen atom comes from one monomer unit and an oxygen and a
hydrogen atom come from the adjacent monomer, forming H2O.
Polyesters
Polyesters are synthetic condensation polymers formed from the condensation reaction
between a diacid and a diol (each reactant has two functional groups in the molecule). Since
the number of carbon atom in each reactant can vary, the carbon chain to which the
functional groups are attached is represented by X or Y.
When the molecules react, a water molecule is eliminated from between them, and an ester
functional group (−COO−) is formed, linking the monomers together.
When thousands of these monomers are linked together alternately in chains with an ester group between
adjacent ones, a polyester forms.
An example of a polyester is polyethylene terephthalate (PET), also known by brand names such as
Terylene or Dacron, used to make clothing, bed sheets, towels, boat sails, carpets, and PET bottles for soft
drinks
4. Polymers
Polyamides
Polyamides are synthetic or natural condensation polymers containing the amide functional group
(−CONH−).
Synthetic polyamides
These are made from a diacid and a diamine (which has two amino −NH2
functional groups).
When these two molecules react with each other, a water molecule is eliminated from between them and an
amide functional group forms, linking the two together (amide linkage).
Nylon is a synthetic polyamide used to make fishing lines, seatbelts, carpets, and clothes.
Natural polyamides
Proteins are natural polyamides formed by linking amino acid monomers together. Amino
acids have an amino group and a carboxyl group. The variable hydrocarbon group in an
amino acid molecule is represented by R, which may contain other atoms such as carbon,
hydrogen, nitrogen, oxygen, and sulphur. There are 20 different groups, making 20
different amino acids. An amino acid molecule
The amide linkage is also known as the peptide linkage.
Examples of proteins include keratin (found in hair and nails) and collagen (found in connective tissues in the
body). Other chemicals such as haemoglobin, enzymes, antibodies, and many hormones are also made of
protein.
4. Polymers
Polysaccharides
Polysaccharides are natural condensation polymers containing the ether functional group
(−O−). They are formed when monosaccharides such as glucose, fructose, and galactose are
linked together.
When glucose undergoes condensation polymerisation, starch is formed.

A glucose molecule
n C6H12O6 → (C5H10O5)n + n H2O
Starch is used to produce energy during respiration in living organisms after being digested to glucose.
Cellulose, another polysaccharide, is used to build cell walls of plant cells.
The environmental impact of synthetic polymers
Plastics are made from a non-renewable resources (petroleum), so their manufacture contributes to the
depletion of petroleum worldwide. During their manufacture, various toxic chemicals are released into the
environment.
Most plastic are non-biodegradable, so plastic waste builds up in the environment which causes land and
water pollution. This can harm aquatic organisms by causing death by ingestion or suffocation. The World
Wildlife Fund (WWF) found that 70% of deep-sea fish have eaten plastic.
Plastic produces dense smoke and poisonous gases when burnt, which can lead to air pollution and health
issues (e.g., asthma, immune system damage, cancer).
Many plastics are flammable, and so pose fire hazards.

4. Polymers
OF A
Nylon is a macromolecule which is held together by the The molecule shown below can be used to produce
same linkage as a protein molecule. What is the name given polymers which are very useful in industry.
to this type of linkage?
(A) Amide bond

(B) Double bond
(C) Ester linkage A partial structure of the polymer is shown below.
(D) Ether linkage
The answer is (A) Amide bond.
Typical Exam Question / 2017 CSEC Chemistry Paper 01 (i) Name the functional group (link) present in the
polymer. (1 mk)
Glucose is converted to starch or cellulose by
(ii) Name the type of polymerisation reaction that
(A) condensation polymerisation has taken place, and state ONE possible use of
(B) addition polymerisation these types of polymers. (2 mks)
(C) oxidation and reduction (iii) Name the by-product that is formed in this
(D) dehydrogenation polymerisation reaction. (1 mk)
The answer is (A) condensation polymerisation. i/ester group
ii/Condensation polymerisation; perfumes

iii/Water
A polymer has the structure
−CHX−CH2−CHX−CH2−CHX−CH2−CHX−CH2
The formula of the monomer is
(A) XCH2−CH2X
(B) CH3=CHX
(C) CH3−CH2X
(D) CH2=CHX
The answer is (D) CH2=CHX.

(CSEC Chemistry) Section B Notes and ESQs

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CSEC CHEMISTRY / SECTION B – ORGANIC CHEMISTRY

1. Sources of Hydrocarbon Compounds

The process by which large molecules of hydrocarbon are

(C) polymerization (1 mk)

(D) condensation (ii) State ONE use of Fraction 2. (1 mk)

See answers in the ‘Exam-style questions’ section

• identify natural gas and petroleum as natural sources of hydrocarbons;

1. Sources of Hydrocarbon Compounds

Components of natural gas

1. Sources of Hydrocarbon Compounds

The vapours rising up the tower pass

Each fraction in this process is a mixture of

Fraction Boiling point (℃) Number of carbon atoms

1. Sources of Hydrocarbon Compounds

1. Sources of Hydrocarbon Compounds

Typical Exam Question / 2003 CSEC Chemistry Paper 01

The process by which large molecules of hydrocarbon are

ii/lightest: natural gas; heaviest: bitumen

iii/resp.: cooking gas; paving roads, roofing material

1. Sources of Hydrocarbon Compounds

The answer is (C) Methane. ii/thermal cracking involves heating alkanes to

2. Organic Chemistry – An Introduction

See answers in the ‘Exam-style questions’ section

2. Organic Chemistry – An Introduction

For example, for butanoic acid (with functional group -COOH):

• its molecular formula is C4H8O2

2. Organic Chemistry – An Introduction

2. Organic Chemistry – An Introduction

2. Organic Chemistry – An Introduction

For example, the general formula of the alkane series is CnH2n+2.

Each homologous series has the following characteristics:

• All members of the series have the same functional group.

number of carbon prefix 5 pent-

2. Organic Chemistry – An Introduction

Alkene CnH2n carbon-carbon prefix + ene ethene

CH2 = CH2 or C2H4

Alcohol/ CnH2n+1OH hydroxyl group prefix + anol ethanol

Alkanoic CnH2n+1COOH carboxyl group prefix + ethanoic acid

2. Organic Chemistry – An Introduction

Structural isomers of straight chain molecules can be formed in two ways:

• by the chain of carbon atoms becoming branched

• by the position of the functional group changing position

2. Organic Chemistry – An Introduction

The name of a branched chain molecule is made up of three parts:

The name of the compound is 2-methylbutane.

This compound is 2,3-dimethylbutane.

2. Organic Chemistry – An Introduction

(B) (i) Name the homologous series to which Compounds

(C) (ii) State the name of EACH compound.

The answer is (D) General formula – CnH2n+2. All other

2017 CSEC Chemistry Paper 01

The answer is (C).

2. Organic Chemistry – An Introduction

Which of the following correctly identifies the homologous

(A) iii/a and b (alkenes) – both have a carbon-carbon double

3. Reactions of Carbon Compounds

Which of the following BEST describes what will be observed

See answers in the ‘Exam-style questions’ section

Candidates should be able to:

• describe the reactions of alkanes and alkenes;

3. Reactions of Carbon Compounds

3. Reactions of Carbon Compounds

The complete combustion of methane is: