ORGANIC CHEMISTRY I

Organic chemistry is the study of compounds of carbon excluding oxides,

carbonates and hydrogen carbonates.
Carbon can form very large number/types of compounds because of its ability to:
i) Use all its valence(outermost) electrons to form four covalent bonds with other
carbon atoms and with atoms of other elements
ii) Form single, double and triple bonds with other carbon atoms and atoms of other
elements
iii) Join each other, via covalent bonds, to form very long chains(catenation)

Hydrocarbons are compounds which are made up of carbon and hydrogen only.
Hydrocarbons are classified in three groups depending on the type of bond between
individual carbon atoms in the molecule. The groups are called homologous series
and they include; alkanes, alkenes and alkynes.

Alkanes
Alkanes form a group of hydrocarbons whose carbon atoms in the molecule are
linked by single covalent bonds. Hydrocarbons in which only single covalent bonds
are present in their structure are said to be saturated. Therefore alkanes are
saturated.

Sources of alkanes
Alkanes occur naturally in crude oil, natural gas and in biogas. Crude oil is mined
from oilfields and is a complex mixture of hydrocarbons. The alkanes in crude oil
have to be separated into various useful components through refining. Natural gas
occurs with crude oil and as gas deposits separately. Biogas can be generated from
domestic refuse using biomass digesters.
 Natural gas mainly contains methane(80%), ethane, propane and butane
 Crude oil contains all alkanes
 Biogas contains between 60-75% methane

Refining of crude oil

 Since crude oil is a mixture of hydrocarbons with different but close boiling
points, the components can be separated by fractional distillation
 After removing solid and gaseous impurities, crude oil is heated to about 500 oC
and the now hot oil is fed into the fractionating column (tower) at the bottom
 Heavier components(fractions) that are solids e.g. asphalt and tar, remain at the
bottom as liquids are removed
 The liquids vapourize and rise up the tower passing a series of bubble caps in
trays where they condense.
 Fractions with lower boiling points e.g. kerosene and gasoline condense into
liquids near the top and are removed. Gaseous fractions are removed at the top
of the tower.
 Fractions with higher boiling points e.g. lubricating oil and diesel oil condense
into liquids mid-tower
 Each fraction is however not pure but a mixture of alkanes with close boiling
points.

Organic Chemistry I 2018 1

 The different fractions of crude oil have different uses as listed in the table
below;

Name of No. of Boiling Uses

fraction carbon point
atoms (oC)
Natural gas 1-4 below 40 Domestic fuel, chemical synthesis of
solvents
Gasoline 4-12 40-200 Fuel for light engines
Kerosene 7-14 200-250 Domestic fuel, jet fuel
Diesel 15-25 300-350 Fuel for heavy engines
Oils 20-70 350-500 Lubricating moving parts
Bitumen Above 70 above Road paving, water-proofing roofs
500

Cracking of hydrocarbons
 Short chain alkanes (up to C12) are in more demand than the long chain alkanes.
Therefore the long chain alkanes must be converted to short chains through a
process called cracking.
 The process can be done through heating alone (thermal cracking) or through
heating in the presence of a catalyst (catalytic cracking). The catalyst is usually
a powdered mixture of silica and alumina. Cracking can be represented by the
equation below:

Long chain alkane 400oC-700oC Short chain alkane + Alkene(s) +

Hydrogen

 Cracking of alkanes in crude oil is a major source of hydrogen for industrial use
e.g. Haber process, manufacture of hydrochloric acid, fuel cells etc.

2CH3CH2CH3 600-700oC CH4 + CH2=CH2 + CH3CH=CH2 + H2

Organic Chemistry I 2018 2

 SiO 2/Al2O3

Nomenclature
 Nomenclature is a systematic naming of compounds. Alkanes have names that
end with a suffix –ane. Their names have a prefix that denotes the number of
carbon atoms in the chain; meth-(1), eth-(2), prop-(3), but-(4), pent-(5), hex-
(6), hept-(7), oct-(8), non-(9) and dec-(10)
 Molecular formula shows the number of atoms present in a molecule
 Structural formula shows the number of atoms and how they are bonded to
one another in a molecule

Table 3.2 List of the first ten alkanes (KLB pg 91)

 Consecutive members of the alkane series differ by a –CH2 unit and conform to a
general formula CnH2n+2, where n=1,2,3,4…..
 Homologous series is a group of compounds with similar chemical properties,
chemical formulae and show gradual change in physical properties. Alkanes,
alkenes and alkynes are examples of homologous series.
 The homologous series of alkanes has the following characteristics;
a) Have a general formula of CnH2n+2 where n is the number of carbon atoms
b) All members show similar chemical properties
c) The physical properties of the members gradually change
d) General method is applied in preparing any member of the series

Branched alkanes and isomerism

 Alkanes can exist as single continuous chain of carbon atoms called straight
chain alkanes. However in other alkanes, carbon atoms branch off the main
chain to form branched alkane
 As a result, alkanes with more than three carbon atoms have the ability to
form molecules with the same molecular formula but different structures
 Isomers are compounds with the same molecular formula but different
structural formula.
 Isomerism is the existence of compounds with the same molecular formula
but different structural formula
 Isomers differ in physical properties e.g. melting and boiling points and
density, but have similar chemical properties.
 If any hydrogen attached to alkane chain is removed, a radical is formed. The
suffix -ane in the alkane is replaced by –yl. Examples;

Alkane Alkyl group/radical

Methane CH4 Methyl- CH3-
Ethane CH3CH3 Ethyl- CH 3CH2-
Propane CH3CH2CH3 Propyl- CH3CH2CH2-

 If any hydrogen atom attached to a middle carbon atom in a chain is replaced

by an alkyl group, a branched alkane is formed.
Naming branched alkanes is based on the following rules;
1. The longest continuous carbon chain is identified to determine the “parent
alkane”

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 2. The carbon atoms in the longest continuous chain are numbered such that
the carbon atom(s) to which the branches are attached take the lowest
number possible
3. Identify the branches. In case there are two or more similar substituents in
the chain, their position are indicated using the prefixes; di-, tri-, tetra-, etc.
Commas(,) are used to separate numbers while hyphens(-) are used to
separate numbers from words
4. When substituents are halogen(s) and alkyl group(s) the halogen is placed
before the alkyl group. The prefixes used for halogens are; fluoro-(fluorine),
chloro-(chlorine), bromo-(chlorine) and iodo-(iodine).

Examples
Name the following compounds;
a) H CH3 H H
| | | |
H-C-C-C-C-H
| | | |
H H H H

b) H CH3 H H
| | | |
H-C-C-C-C-H
| | | |
H H CH3 H

c) H CH3 H
| | |
H-C-C-C-H
| | |
H CH3 H

d) H CH3 H H H
| | | | |
H-C-C-C-C-C-H
| | | | |
H H H H H

e) H CH3 H H
| | | |
H-C-C-C-C-H
| | | |
H H Cl H

f) H Br H H
| | | |
H-C-C-C-C-H
| | | |
H H Br H

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 Give the structural formula of the following compounds;
a) 2-methylheptane
b) 2,2,4-trimethylpentane
c) 3-ethylhexane
d) 2,2,3-trimethylhexane

Laboratory preparation of alkanes

 Alkanes are prepared in the laboratory by the reaction of sodium alkanoate
and soda lime (mixture of sodium hydroxide and calcium oxide). An
alkanoate is a salt of organic acid

DIAGRAM

CH3COONa(s) + NaOH(s) heat CH 4(g) + Na2CO3(s)

(sodium ethanoate) (from soda lime) (methane)

CH3CH2COONa(s) + NaOH(s) heat CH 3CH3(g) +

Na2CO3(s)
(sodium propanoate) (from soda lime) (ethane)

 Generally; Sodium alkanoate + NaOH Alkane + Na 2CO3

Physical properties
 Methane is non-poisonous, colourless gas (C 1-C4-gases, C5-C10-liquids)
 It is slightly soluble in water – collected over water
 Alkenes are highly soluble in organic solvents e.g. tetrachloromethane,
methylbenzene
 Generally, solubility of alkanes decreases with increase in molecular mass.
This is because as the molecular size increases, the intermolecular forces of
attraction become stronger
 Melting and boiling points increase with increase in molecular mass. As the
number of carbon atoms in the molecular increase, the intermolecular forces
of attraction become stronger.

Chemical properties
 Methane burns in excess air with a pale blue flame(non-luminous) to form
carbon (IV) oxide and water

CH4(g) + 2O2(g) CO 2(g) + 2H2O(l)

 In limited supply of air, the flame is luminous (yellow and sooty) due to
incomplete combustion. The products are carbon (II) oxide and water.

CH4(g) + O2(g) CO(g) + 2H 2O(l)

 All alkanes behave in a similar manner.
 Alkanes react with halogens only in the presence of sunlight. The sunlight
provides the energy necessary for splitting the halogen molecule into free

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 atoms. The free atoms are very reactive and replace hydrogen atoms in the
alkane molecule.
 A reaction in which one atom or group of atoms in a molecule is replaced by
another is called a substitution reaction.
 Chlorine reacts with methane in the presence of sunlight (U.V. rays). It
replaces the hydrogen atoms in methane repeatedly as shown below;

U.V. light
CH4(g) + Cl2(g) CH3Cl(g) + HCl(g) chloromethane

U.V. light
CH3Cl(g) + Cl2(g) CH2Cl2(g) + HCl(g) dichloromethane

U.V. light
CH2Cl2(g) + Cl2(g) CHCl3(g) + HCl(g) trichloromethane

U.V. light
CHCl3(g) + Cl2(g) CCl4(g) + HCl(g) tetrachloromethane

 A similar reaction takes place between methane and bromine though slower.
Bromine is decolourised when left in the sunlight with methane as
bromomethane is formed.

U.V. light
CH4(g) + Br2(g) CH3Br(g) + HBr(g)

Uses of alkanes
1. Methane, ethane, propane and butane are used as domestic fuel in form of LPG.
2. Liquid alkanes are constituents of petrol, kerosene diesel and lubricating oils
used in running engines.
3. Alkanes are used to manufacture carbon black – a component of printing ink and
paint.
4. Alkenes are used to manufacture industrial solvents such as methanol,
methanal, chloromethane etc.
5. Alkanes are a major source of hydrogen via cracking.

Alkenes
Alkenes are hydrocarbons that contain at least one carbon-carbon double bond in a
molecule. Because of the presence of the double bond in the carbon chain, alkenes
are said to be unsaturated. The first member of the alkene series is ethene, C 2H4
because at least two carbon atoms are necessary for a double bond to be formed.

Table 3.5 (KLB pg 100) first six alkenes

 Alkenes conform to the general formula C nH2n where n=2,3,4.... The carbon-
carbon double bond in alkenes determines their chemical properties thus it is
their functional group.
 A functional group is an atom/group of atoms which is/are responsible for the
characteristic reactions of a group of compounds.

Nomenclature
Alkenes are named in a similar way as alkanes but the longest straight carbon chain
must contain the carbon-carbon double bond. The prefix indicating the number of

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carbon atoms in the chain is followed by the suffix –ene. Alkenes are named by the
following rules;
1. The parent name of the alkene is determined by identifying the longest
continuous carbon chain containing the carbon-carbon double bond
2. The carbon atoms in the chain are numbered such that the carbon atom with the
double bond takes the least number possible
3. The position(s) of the substituent groups are indicated by position of the carbon
atoms to which they are attached
4. If the double bonds are more than one, the prefixes di-, tri-, tetra-, etc are used
after the positions and before the suffix –ene

Isomerism in alkenes
Isomerism is the existence of compounds with the same molecular formula but
different structural formula. Alkenes show two types of isomerism namely;
branching isomerism and positional isomerism.

Branching isomerism occurs when a substituent group(branch) is attached to one

of the carbon atoms in the chain containing the double bond. Example:

H CH3 H
| | |
H-C=C-C–H 2-methylprop-1-ene (branching isomer of butene)
| |
H H

Positional isomerism occurs when the position of the carbon-carbon double bond
in the alkene chain changes. Example:
But-1-ene and but-2-ene (positional isomers of butene)

H H H H H H H H
| | | | | | | |
H – C =C - C - C – H and H - C - C= C -C-H
| | | | | |
H H H H H H
Questions
Give the systematic names of the following compounds;

a) H H H | | |
| | | H-C=C- C–H
H-C=C-C–H | |
| | H H
H H
d) H H CH3 H
b) H H H H | | | |
| | | | H – C =C - C-C–H
H – C =C - C-C–H | | |
| | | H H H
H H H
e) H Cl CH3 H
c) H CH3 H | | | |

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 H – C =C - C - C – H | | | | |
| | | H-C=C-C-C-C-H
H H H | | | |
H CH3 H H
f) H CH3 H H H

Draw the structural formula of the following compounds;

a) 2,3-dibromobut-2-ene
b) 2-chloro-3-methylpent-2-ene
c) 2,3,3-trimethylhex-1-ene
d) 1,2-dichloroethene

Laboratory preparation of ethene

 Ethanol decomposes between 160-180oC to form ethene and water as shown

below;

C2H5OH(l) conc. H2SO4 CH2CH2(g) + H2O(l)

Heat
 Dehydration is a process where water (or atoms that make up water) are
removed from a substance by a dehydrating agent.
 Concentrated sulphuric (VI) acid acts as a dehydrating agent in this process.
Aluminium oxide may be used as both a dehydrating agent and a catalyst in
a similar reaction.
 Sodium hydroxide solution is used to remove traces of sulphur (IV)
oxide(from decomposition of sulphuric (VI) acid) and carbon (IV) oxide(from
decomposition of ethanol)
 Broken porcelain/sand is used to absorb excess heat produced and reduce
bumping which may crack the flask.

Physical properties of alkenes

 Ethene is a colourless gas, slightly soluble in water, less dense than water
 Alkenes are highly soluble in organic solvents e.g. methylbenzene,
tetrachloromethane etc.
 Solubility of alkenes decreases with increase in molecular mass.

Organic Chemistry I 2018 8

  The melting and boiling points of alkenes generally increase with increase in
the number of carbon atoms in the molecule.

Name of Molecular Melting point Boiling Density

(o
alkene formula C) point (g/cm3)
(oC)
Ethene C2H4 -169 -104 0.5013
Propene C3H6 -185 -48 0.5193
But-1-ene C4H8 -185 -6 0.5951
Pent-1-ene C5H10 -138 30 0.6405
Hex-1-ene C6H12 -98 64 0.6731

Chemical properties of alkenes

Combustion
 All alkenes burn in air with a yellow and sooty flame. This is because they are
unsaturated thus have a high carbon content(e.g. 85.7% by mass for ethene)

C2H4(g) + 3O2(g) 2CO2(g) + 2H2O(l)

Addition Reactions
 Addition reactions are those reactions in which one molecule/atom adds
onto another to form a single product (usually saturated)
 New atoms can be added to alkene molecules by breaking the double carbon-
carbon bond and saturating the carbon atoms through four single bonds
 Examples of addition reactions for alkenes include: halogenations,
hydrohalogenation, hydrogenation, self-addition, reaction with oxidising
agents, reaction with concentrated sulphuric (VI) acid and hydration.

a) Halogenation – Addition of halogen atoms across a double bond.

i) Chlorine and bromine are decolourised immediately when ethene is
added.
H H Br Br
| | | |
C = C + Br2 H – C – C – H 1,2-dibromoethane
(C2H4Br2)
| | | |
H H H H

H H Cl Cl
| | | |
C=C + Cl2 H–C–C–H 1,2-dichloroethane
(C2H4Cl2)
| | | |
H H H H

ii) Bromine water (mainly HOBr) is decolourised when ethene is bubbled

through.

Organic Chemistry I 2018 9

 H H Br OH
| | | |
C = C + HOBr H–C–C–H 2-bromoethanol
(CH2BrCH2OH)
| | | |
H H H H
This reaction serves as a test for alkenes.

b) Hydrohalogenation – Addition of hydrogen halides i.e. HCl, HF, HBr, HI.

Example;

H H Br Br
| | | |
C=C + HBr H–C–C–H 1,2-dichloroethane
(C2H4Br2)
| | | |
H H H H

c) Hydrogenation – Addition of hydrogen to alkenes at 150-250 oC in the presence

of nickel catalyst to form alkanes.

H H H H
| | Nickel | |
C=C + H2 H– C – C – H ethane (C2H6)
| | 150-250oC | |
H H H H
Hydrogenation is applied in the conversion of liquid oil to solid oil/fat such as in
the manufacture of margarine.

d) Self-addition
 Alkene molecules have the ability to react with each other to form a large
molecule with a larger molecular mass. The double bonds are broken down
and a continuous chain of single carbon-carbon bonds is formed
 Each small molecule is called a monomer and the large molecule formed is
called a polymer. Polymerisation is the process where several monomers
combine to form a large molecule (polymer)
 When ethene is polymerised, the larger molecule formed is called polyethene
(polythene)

H H H H H H H H
| | | | | | | |
C=C + C=C C C C C
| | | | | | | |
H H H H H H H H
Ethene Ethene (Polyethene)
(monomer) (monomer) (polymer)

 Generally, polymerization of alkenes can be represented as shown below;

Organic Chemistry I 2018 10

 H H H H
| | | |
n C= C C C where
n=2,3,4,5,6…..∞
| | | | n
H H H H

e) Reaction with oxidising agents

i) If purple acidified potassium manganate (VII) solution is shaken with ethene,
it becomes decolourised. The manganate (VII) ions add oxygen to the double
bond because it is an oxidising agent.

H H OH OH
| | | |
C= C H+/KmnO4 H–C–C–H (ethan-1,2-diol)
| | | |
H H H H

It changes colour from purple to colourless. This reaction also serves as

at test for alkenes.

ii) Orange acidified potassium dichromate (VI) turns green on reacting with
ethene.

H H OH OH
| | | |
C= C H+/K2Cr2O7 H–C–C–H (ethan-1,2-diol)
| | | |
H H H H

f) Reaction with concentrated sulphuric (VI) acid

Ethene reacts with concentrated sulphuric (VI) acid at room temperature to form
ethylhydrogen sulphate.

H H H HSO 4
| | | |
C= C + H2SO4 H–C–C–H ethylhydrogen sulphate
| | | |
H H H H

 When warmed with water, ethylhydrogen sulphate forms ethanol and the
sulphuric (VI) acid is recovered. The reaction is called an hydrolysis

H HSO4 H OH
| | | |
C= C H2O H–C–C–H + H2SO4
| | | |
H H H H

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  Hydrolysis is the reaction of a compound with water such that the
hydroxyl group(OH) of the water is remains intact.(one or both H and OH
are added to substance during hydrolysis)

g) Hydration
A mixture of ethene and steam react when heated to 300 oC, at high pressure
and in the presence of phosphoric (V) acid catalyst to form ethanol. This reaction
involves addition of water to ethene and is called hydration.

H H H OH
| | | |
C= C + H2O phosphoric (V) acid H–C–C –H
| | 300oC | |
H H H H

Test for alkenes

i) Ethene decolourises bromine water(changes colour of bromine water from
orange to colourless)
ii) It also decolourises acidified potassium manganate(VII) solution(changes
colour from purple to colourless)

Uses of alkenes
1. Ethene is used to manufacture polythene and other plastics
2. Ethene is used to manufacture ethanol
3. Ethene is used for ripening fruits
4. Alkenes are used t manufacture soapless detergents
5. Manufacturing ethan-1,2-diol (glycol) used as a coolant in car engines.

Alkynes
Alkynes form a homologous series that contains a carbon-carbon triple bond in their
molecules

Table 3.8(KLB pg 109) first 9 alkynes

 Alkynes conform to the general formula C nH2n-2 where n=2, 3, 4, 5….. The first
alkyne member has n=2 because at least two carbon atoms are required to have
a triple carbon-carbon bond.
 The presence of the triple bond results in unsaturation of alkynes. The -C≡C- is
the functional group of alkynes.

Nomenclature
Alkynes are named in a similar way as alkenes. Alkynes though have names ending
in –yne. The prefix indicating the number of carbon atoms in the chain is followed
by the suffix –yne.
1. The longest continuous carbon chain with the triple bond provides the “parent
name”
2. The carbon atoms are numbered such that the triple carbon-carbon bond takes
the least number possible

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3. The position of the triple bond is indicated in the name before the suffix. Also the
position of a substituent, if any, is included in the name.

Isomerism in alkynes
Alkynes show two types of isomerism i.e. branching isomerism and positional
isomerism
 Branching isomerism occurs when a substituent group (branch) is attached to
a straight chain alkyne. Example;
H H H H H
| | | | |
H-C≡C-C-C-H and H - C≡ C - C -C - C – H (branching isomers
of pentyne)
| | | | |
CH3 H H H H
(3-methylbut-1-yne) (pent-1-yne)

 Positional isomerism occurs when the position of the triple bond in the longest
carbon chain changes. Example;

H H H H
| | | |
H–C≡C–C–C–H and H – C - C ≡ C – C – H (positional isomers
of butyne)
| | | |
H H H H
(but-1-yne) (but-2-yne)

Questions
Give the systematic names of the following compounds
a) H H H c) H Br H
| | | | | |
H - C≡ C - C -C - C – H H - C≡ C - C -C - C – H
| | | | | |
CH3 H H H Br H

b) CH3 H H d) CH3 H
| | | | |
H - C≡ C - C -C - C – H H - C≡ C - C -C - H
| | | | |
CH3 H H CH3 H

Draw the structural formula of the compounds below;

a) 3-chloro-3-methylpent-1-yne
b) 3-methylpent-1-yne
c) Isomers of pentyne
d) Isomers of hexyne

Laboratory preparation of ethyne

Calcium carbide reacts with water at room temperature to form calcium hydroxide
solution and ethyne.

Organic Chemistry I 2018 13

 CaC2(s) + H2O(l) C2H2(g) + Ca(OH)2(aq)

The set-up is shown below.

DIAGRAM

The reaction is exothermic. To avoid the flask from cracking, some sand is added to
absorb excess heat. At the beginning of the experiment the flask should be
completely dried to avoid the formation of the gas before completing the set-up.

Physical properties of alkynes

Alkyne Molecular Melting Boiling Physical Density

formula point(oC) point(oC) state at (g/cm3)
r.t.p.
Ethyne C2H2 -82 -84 Gas 0.62
Propyne C3H4 -103 -23 Gas 0.67
But-1-yne C4H6 -122 8 Gas 0.69
Pent-1-yne C5H8 -90 39 Liquid 0.72
Hex-1-yne C6H10 -132 71 Liquid 0.71
Hept-1-yne C7H12 -80 100 Liquid 0.73

 Ethyne is a colourless gas with a pleasant smell when pure. It is slightly soluble
in water(collected over water)
 Alkynes however, dissolve better in non-polar solvents.
 Alkynes with lower molecular masses are gases at room temperature

Chemical properties of alkynes

Combustion
 Like other hydrocarbons, alkynes burn in air forming an oxide of carbon with
water and produce a lot of heat. However their flames are very smoky due to
higher carbon content (92.3% in ethyne) in their molecules.
 The products of combustion depend on the supply of air. In excess air, ethyne
burns in air to give carbon (IV) oxide and water;

2C2H2(g) + 5O2(g) excess air 4CO2(g) + 2H2O(l)

 In limited air, it forms carbon (II) oxide, carbon and water, making the flame very
sooty;

C2H2(g) + O2(g) limited air CO(g) + C(s) + H 2O(l)

Addition Reactions
Alkynes are more unsaturated than alkenes because of the triple carbon-carbon
bond in their molecules. Therefore, more atoms may be added across the triple
bond to form saturated compounds. As such, addition reactions in alkynes are more
rapid than in alkenes.

i) Reaction with hydrogen (hydrogenation)

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In the presence of nickel catalyst, ethyne reacts with hydrogen to form ethene first,
then ethane.

H H
Nickel | |
H-C≡C-H + H2 C=C ethene
(C2H4)
200oC | |
H H

H H H H
| | Nickel | |
C=C + H2 H–C–C–H ethane
(C2H6)
| | 200oC | |
H H H H

ii) Reaction with halogens (halogenation)

 Red-brown bromine vapour is decolourised when reacted with ethyne. This
reaction takes place in two steps as shown below;

Br Br
| |
Step I H-C≡C-H + Br2 C=C 1,2-dibromoethene
(C2H4Br2)
| |
H H

Br Br Br Br
| | | |
Step II C=C + Br2 H–C–C–H 1,1,2,2-
tetrabromoethane
| | | |
H H Br Br
 Chlorine is explosive with ethyne. It is diluted with an inert gas to have a
moderate reaction that takes place in two steps as shown below;
Cl Cl
| |
Step I H-C≡C-H + Cl2 C=C 1,2-dichloroethene
(C2H4Cl2)
| |
H H

Cl Cl Cl Cl
| | | |
Step II C=C + Cl2 H–C–C–H 1,1,2,2-
tetrachloroethane
| | | |

Organic Chemistry I 2018 15

 H H Cl Cl

iii) Reaction with hydrogen halides (hydrohalogenation)

Ethyne does not readily react with hydrogen halides. Hydrogen iodide reacts
with ethyne at room temperature while hydrogen bromide and hydrogen
chloride require warming. However the reaction with hydrogen chloride is very
slow.

I H
| |
a) H-C≡C-H + 2HI H-C–C-H 1,1-
diiodoethane
| |
I H

Br H
| |
b) H-C≡C-H + 2HBr H-C–C-H 1,1-
dibromoethane
| |
Br H

Cl H
| |
c) H-C≡C-H + 2HCl H-C–C-H 1,1-
dichloroethane
| |
Cl H

Test for alkynes

 The tests for alkynes are similar to those of alkenes in which bromine water and
acidified potassium manganate (VII) are decolourised.
 However the decolourisation is faster in alkynes than in alkenes.

Uses of alkynes
1. Ethyne with oxygen burns with a very hot flame(oxy-acetylene flame) which is
used to weld and cut metals
2. Used as starting materials in the manufacture of important chemical reagents
and solvents
3. In the industrial manufacture of compounds such as adhesives and plastics
4. Manufacture of synthetic fibres such as rayon

Organic Chemistry I 2018 16