HYDROCARBONS

The binary compounds of carbon and hydrogen are called hydrocarbon.

or
Compound which contains only carbon and hydrogen are called hydrocarbons.
The simplest class of organic compounds is hydrocarbons (compounds consisting of
only carbon and hydrogen elements). Carbon is the only element capable of forming stable,
extended chains of atoms bonded through single, double, or triple bonds. Hydrocarbons
are divided into four general classes, depending upon the nature of bonds present in their
molecules. These are alkanes, alkenes, alkynes and aromatics. Each carbon atom of a
hydrocarbon has four bonds.
They are gases or volatile liquids and their volatility decreases with the increase of
molecular mass. That is the reason low molecular mass hydrocarbons are gases at room
temperature, such as: CH4 and C2H6. Moderate molecular mass hydrocarbons are liquids,
such as, C6H14; while higher molecular mass hydrocarbons are solids.
Fossil fuels are hydrocarbons. Hydrocarbons are the starting materials for the synthesis of
organic chemicals of commercial importance. These chemicals are essential for making
plastics, synthetic rubbers, synthetic fibres and fertilizers, etc.
Classification of hydrocarbons:
Hydrocarbons are of different types. They can be classified into two main type
depending upon the structure of hydrocarbon
1. Open chain hydrocarbons (acyclic)
2. Closed chain hydrocarbons (cyclic)
1. Open chain hydrocarbons :-( acyclic)
Open chain hydrocarbons are those in which the end carbon atoms are not joined with
each other, in this way they form a long chain of carbon atoms.
The hydrocarbons present in open structure in which both ends are not interconnected
with each other. These are also called aliphatic hydrocarbons. (Greek alephs mean fat) many
animals and plants fat contain these hydrocarbons.
These chains may be either straight or branched.
Straight chain compounds are those in which carbon atoms link with
each other through a single, double or triple bond forming a straight chain.
H2 H2
C C
C C C C C H3C C CH3
H2
n-Pentane

Branched chain compounds are those in which there is a branch along a

straight.
CH3

CH CH3
C C C C C H3C C
H2
C Iso-Pentane
 Open chain hydrocarbons are further divided into two types.
a) Saturated hydrocarbon
b) Unsaturated hydrocarbon.
a. Saturated hydrocarbon: -
Those open chain or aliphatic hydrocarbons in which all carbon atoms are linked
through single covalent bond are called saturated hydrocarbons or alkanes or paraffin’s.
CH3CH3 ethane.
Alkanes or paraffins (Latin : parum little; affinis, affinity).
Hydrocarbons in which all the carbon atoms are linked to one another by only single
bonds are called alkanes or saturated hydrocarbons.
The alkanes are the simplest class of organic molecules because they contain no
functional groups. alkanes are the simplest class of organic compounds. They are made
of carbon and hydrogen atoms only and contain two types of bonds, carbon-hydrogen
(C—H) and carbon-carbon (C—C) single covalent bonds.
H2 H2 H2 H2 H2 H2
H3 C C C CH3 H3C C C C C CH3
n-Butane n-Hexane

b. Unsaturated hydrocarbon: -
Those open chain or aliphatic hydrocarbons in which at least two carbon atoms
are linked through multiple bond. i.e. (double or triple bond) are called unsaturated
hydrocarbons.
The unsaturated hydrocarbons are further classified into two types.
i) Alkenes or olefins
ii) Alkynes or acetylenes.
i. Alkenes or olefins: -
Unsaturated open chain hydrocarbons that contain a carbon-carbon double bond or
bonds are known as alkenes or olefins (olefins are a Latin word (oil forming or making)
e.g. CH2 = CH2 ethene
ii. Alkynes or acetylenes: -
Unsaturated open chain hydrocarbons that contain a carbon-carbon triple bond or
bonds are known as alkynes or acetylenes e.g. CH  CH ethyne or acetylenes.
2. Closed chain or cyclic hydrocarbons: -
3. Closed chain or cyclic hydrocarbons are those in which the carbon atoms at the end of
the chain are not free. They are linked to form a ring.
The hydrocarbons in which carbons atoms are joined or linked through covalent bonds
in such way to form ring are called closed chain or cyclic hydrocarbons.

Benzene Cyclohexane
The closed chain or cyclic hydrocarbons are further classified into two types.
a) Alicycle hydrocarbons.
b) Aromatic hydrocarbons.
i. Alicyclic hydrocarbons: -
Cyclic hydrocarbons which consist only carbon atoms are called alicyclic.
 hydrocarbons may be
i) Cycloalkanes

Cyclobutane Cyclopropane
ii) Cycloalkenes

Cyclohexene Cyclopentene
iii) Polycyclic

Bicyclo[1,1,0]butane

ii. Aromatic hydrocarbons: -

The hydrocarbons which consist of benzene and all compounds that have
structures and chemical properties like benzene are called aromatic hydrocarbons aroma
(Greek means) odour
Aromatic hydrocarbons may
i) Monocyclic aromatic hydrocarbons
CH3

Cl
Benzene 3-Chlorotoluene
ii) Polycyclic aromatic hydrocarbons

Naphthalene Anthracene
 Alkanes or Saturated Hydrocarbons: -
Hydrocarbons in which all the carbon atoms are linked to one another by only single
bonds are called alkanes or saturated hydrocarbons.
In IUPAC system saturated acyclic hydrocarbons are called alkanes.
General Formula of Alkanes CnH2n+2
Where n= 1, 2, 3, --------------
The simplest hydrocarbons are alkanes. In these compounds, all the bonds of carbon
atoms are single that means valences of carbon atoms are saturated. Therefore, they are
least reactive. That is the reason, alkanes are called paraffins (para means less, and
affins means affinity or reactivity).
Types of Carbon and Hydrogen atoms in Alkanes: -
The carbon atoms in an alkane molecule may be classified into four types.
i. Primary Carbon (1o) atom.
ii. Secondary Carbon (2o) atom.
iii. Tertiary Carbon (3o) atom.
iv. Quaternary Carbon (4o) atom.
1. Primary Carbon Atom: -
A carbon atom attached to one other (or no other) carbon atom is called a primary
carbon atom and denoted as 1o carbon.
2. Secondary Carbon Atom: -
A carbon atom attached to two other carbon atoms is called a secondary carbon atom
and denoted as 2o carbon.
3. Tertiary Carbon Atom: -
 A carbon atom attached to three other carbon atoms is called a tertiary carbon atom
and denoted as 3o carbon.
4. Quaternary Carbon Atom: -
A carbon atom attached to four other carbon atoms is called a quaternary carbon atom
and denoted 4o carbon.
The hydrogen atoms attached to 1o, 2o and 3o carbon atoms are called primary (1o),
secondary (2o) and tertiary (3o) hydrogen atoms. There is no quaternary hydrogen atom.
Since quaternary carbon does not carry any hydrogen atom.

Types of Alkanes
Alkane can be classified as given below.
a. Straight Chain Alkanes.
b. Branched Chain Alkanes.
c. Cyclo alkanes.
a. Straight Chain Alkanes: -
The alkanes containing straight chain or alkanes in which no carbon atom is
linked to more than two other carbon atoms are called straight chain alkanes.
H2 H2 H2 H2 H2 H2
H3 C C C CH3 H3C C C C C CH3
n-Butane n-Hexane
b. Branched Chain Alkanes: -
The alkanes in which a straight chain is not present or alkanes in which at least
one carbon is attached to more than two carbon atoms are called branched chain
alkanes.
CH3
H H2
H H3C C C CH3
H3C C CH3 H3C C CH3

CH3 CH3 CH3

2-Methylpropane 2-2, Dimethylpropane 2-methylbutane

c. Cycloalkanes (closed chain alicyclic): -

Cycloalkanes or cyclo paraffins are saturated hydrocarbons in which the carbon
atoms are joined by single covalent bonds to form a ring. They are also called
 alicyclic compound prefix ali from aliphatic compound is added as cycloalkanes are
resemble in many respects to alkanes.
The first member is cyclopropane C3H6 some common cycloalkanes are.

Cyclo propane Cyclo butane Cyclo pentane Cyclo hexane

IUPAC Nomenclature Rules for Chains Alkanes: -

The following rules are used for naming branched chain alkanes.
i. Longest Chain Rules: -
Select the longest continuous chain of carbon atoms. This is called the parent chain
while all other carbon atoms which are not included in the parent chain are called branch
chains or side chain or substituent. The longest chain may be or may not be look straight must
be continuous.
C C C

C
C C C C C

C C C C C C
C C C
Hexane Octane
ii. Rule for Larger number of Side Chains: -
If two chains of equal lengths are possible one with the larger number of side chains is
selected.
C C C C C C C C C C C C

C C C C C C
Correct 2 side chains Hexane Wrong 1 side chain
iii. Lowest Number Rule or Lowest Sum Rule: -
The number that indicates the position of the substituent on the parent chain is called
the Locant or positional number. If there are two or more substituents, the numbering of
parent chain is done in such a way that the sum of the Locants is the lowest known as lowest
sum rate.
2 1 6 7
C C C C
4 4
C C C C C C C C C C
3 5

C C C C C C
5 6 7 3 2 1
sum of locants = 3 + 4 = 7 sum of locants = 4 + 5 = 9
Correct wrong
 C C C C
1 2 3 4 5 5 4 3 2 1

C C C C C C C C C C

C C C C
sum of locants =2 + 2 + 3 + 4 = 11 sum of locants =2 + 3 + 4+ 4 = 13
Correct wrong
iv. Name of the Branched Chain Alkane: -
Prefix the name of the substituent alkyl group) to the name of the parent alkane and
indicate its positions on the parent chain by writing before it the number of the carbon atom
carrying the substituent. The name of the substituent is separated from its Locates by a
hyphen (-). The final name of the alkane is always written as one word.
Numerical Prefix + Prefix + word Root + Suffix
v. Alphabetical order of the side chains: -
Each alkyl group prefixed by its positional number is arranged in alphabetical order
irrespective of its positional number before the name of the parent alkane.
2 1
Numerical prefixes = 3 , 4
C C
Prefixes = Ethyl , Methyl
C C C C C Word root = Hept
3 4

C C C Suffix = ane

5 6 7 4 - Ethyl - 3 - methylheptane

Numerical prefixes = 2, 3
1 2 3 4 5 6
Prefixes = Ethyl , Methyl
C C C C C C
Word root = Hex
C C C Suffix = ane

3 - Ethyl - 2 - methylhexane
vi. Numbering of Different alkyl group at equivalent position: -
If two different alkyl groups are present at equivalent positions the number of the parent
chain is done in such a way that the alkyl group which comes first in the alphabetical order
(written first in the name) gets the lower number
C
Correct 1 2 3 4 5 6

C C C C C C
6 5 4 3 2 1 Wrong
C C
vii. Naming Some Alkyl Group at Different Positions: -
When same alkyl group occurs more than once on the parent chain at different
positions. The positional number or Locant of each alkyl group is repeated by commas and
suitable prefixes as di (2), tri (3) and
tetra 4) etc. is attached to the name of the alkyl group. C
5 4 3 2 1
However, the prefixes di, tri, tetra etc. are not
considered while deciding the alphabetical order of the C C C C C
alkyl group.
C C
2,3,4-Trimethylpentane
viii. Numbering the Complex Substituents: -
When the substituent on the parent chain is further branched. It is named as a
substituted alkyl group by numbering the carbon atoms of this group attached to the parent
chain as 1. The name of such a substituent may be enclosed in brackets to avoid confusion
with the numbers of the parent chain.
C C
1 2 3 4 5 6 1 3
2
C C C C C C C C C

C C C C C C
7 8 9 10

2,3,4-Trimethyl-6-(-2-methylpropyl)decane

1 2 3 4 5 6 7 8 9 10
C C C C C C C C C C

1
C C

2
C C

3
C

5-(1,2-Dimethylpropyl)decane

Sources of Alkanes:
1. The main sources of alkanes are petroleum and natural gas.
2. Methane forms about 85% of natural gas.
3. All the alkanes are obtained commercially by the fractional distillation of crude
petroleum.
4. Marsh gas is formed by the bacterial decay of vegetable matter contains mostly
methane.
5. Fuel gases obtained from coal gas contain alkanes in small amounts.
6. Methane occurs in gobar gas, sewage gas and biogas which are formed by the
decomposition of cattle dung, excreta and plant wastes.
Preparation of alkanes:
The alkanes are generally purified from the petroleum or natural gas sources,
although there are various methods available for the preparation of the alkanes,
two important methods are given below.
1. Hydrogenation of Alkenes and Alkynes:
Hydrogenation means addition of molecular hydrogen in alkenes and
alkynes.
Alkenes and alkynes are unsaturated compounds, so they have the capacity to add up
atoms in them. This reaction is carried out in the presence of nickel catalyst at 250 °C
to 300 °C. However, in the presence of catalyst platinum or palladium, the reaction
takes place at room temperature.
Ni
CH2 CH2 + H2 CH3 CH3
200-300 oC
 Similarly, alkynes first convert into alkenes then to alkanes.

Ni
HC CH + H2 CH2 CH2
200-300 oC

Ni
CH2 CH2 + H2 CH3 CH3
200-300 oC
2. Reduction of Alkyl Halides:
Reduction means addition of nascent hydrogen.
it is a replacement of a halogen atom with a hydrogen atom. This reaction takes
place in the presence of Zn metal and HCl.
Zn/dil.HCl
CH3Br + 2[H] CH4 + HBr
Zn/dil.HCl + HBr
CH3CH2Br + 2[H] CH3CH3
Physical properties of alkanes:
1. Alkanes form a homologous series of compounds. First four members of the series are
gases. The alkanes consisting of C5 to C10 are liquids while higher members of the
series are solids.
2. They are nonpolar; therefore, they are insoluble in water but soluble in organic
solvents.
3. The density of alkanes increases gradually with the increase of molecular size.
4. The melting and boiling points of alkanes increase regularly with the increase of
molecular sizes. This is because of increase of attractive forces between the molecules
of alkanes.
5. The alkanes become more viscous as their molecular sizes increase.
6. Alkanes become less flammable, i.e. more difficult to burn with the increase of
molecular sizes.
7. Liquids cycloalkanes are soluble in one another.
Chemical properties:
Alkanes are relatively stable. Branched chain alkanes are more stable straight chain.
on the other hand, cycloalkanes are stable except cyclopropane and cyclobutane.
The inertness of alkanes is due to the following reasons.
1. The carbon -hydrogen bond is the least polar.
2. The carbon-carbon bond is completely non-polar.
3. There is no unshared pair of electrons.
4. There is no unsaturation point.
Some of the chemical reactions are given below.
1. Halogenation:
A reaction in which one or more hydrogen atoms of a saturated compound are replaced
with some other atoms (like halogen) is called a substitution reaction.
Alkanes give only substitution reactions. These reactions are a characteristic property of
alkanes. Alkanes react fairly with halogens in diffused sunlight only. In dark there is no
reaction. In direct sunlight, reaction is explosive, and carbon is deposited.
CH + 2Cl Sun light C + 4HCl
4 2
In diffused sunlight, a series of reactions take place and at each step one hydrogen atom is
substituted by halogen atoms, so that all the hydrogen atoms are substituted one by one by
halogen atoms.
+ Cl2 Sun light +
CH4 CH3Cl HCl
Chloromethane
+ Cl2 Sun light
CH3Cl CH2Cl2 + HCl
Dichloromethane
CH2Cl2 + Cl2 Sun light +
CHCl3 HCl
Trichloromethane
CHCl3 Cl2 Sun light
+ CCl4 + HCl
Tetrachloromethane
(Carbon tetrachloride)
2. Combustion:
Alkanes burn in the presence of excess of air or oxygen to produce a lot of heat;
carbon dioxide and water is called combustion.
This reaction takes place in automobile combustion engines, domestic heaters and cooking
appliances. It is highly exothermic reaction and because of it, alkanes are used as fuel.
CH4 + 2O2 CO2 + 2H2O + Heat
In the limited supply of oxygen, there is incomplete combustion. As a result, carbon
monoxide is produced that creates suffocation and causes death.
CH4 + 2O2 CO + 2H2O + Heat

Alkenes or olefins:
Hydrocarbons containing a carbon-carbon double bond are called alkenes. They are
also called olefins.
Or
The unsaturated hydrocarbons that contain one or more carbon-carbon double bonds
(C=C) are called alkenes or olefins.
The simplest alkene is ethene having formula C2H4. The unsaturated hydrocarbons that
contain one or more carbon-carbon double bonds (C=C) are called alkenes or olefins. (
French word olefiant means oil forming because the lower members of alkenes give oily
product on treatment with Chlorine or bromine.
The alkenes are important in the sense that they are more reactive compounds than
the alkanes and are therefore used as the starting material for the preparation of many
important organic compounds.
General Formula CnH2n where n= 2, 3, 4, ……
Common Names: -
Alkane – ane + ylene = Alkylene
IUPAC Names: -
Alk – ane + ene = Alkene
The position of the double bonds is indicated by Greek Letters α, β, …… etc. in the
common system while Arabic numerals i.e. 1, 2, 3, 4, …… etc. are used in IUPAC system.
 Formula Common Name IUPAC
Name
CH2 = CH2 Ethylene Ethene
CH2CH = CH2 Propylene Propene
CH3CH2βCH = αCH
2 α –Butylene But-1-ene
CH3CH = βCHαCH3 β –Butylene But-2-ene
CH3CH2CH2βCH = αCH2 α-Pentylene Pent-1-ene
βCHαCH
CH3CH2CH = 3 β –Pentylene Pent-2-ene
CH3CH2CH2CH2βCH = α -Hexylene Hex-1-ene
αCH
2

Occurrence of alkenes:
1. Alkenes being more reactive than alkanes, seldom occur free in nature.
2. Lower alkenes occur in coal gas in minute quantities.
3. Ethylene is present in natural gas sometimes to the extent of 20%.
4. Alkenes are produced in large amounts by cracking of petroleum.
Preparations of Alkenes or olefins:
Alkenes are prepared by the removal of small atoms (H,OH,X) from the adjacent carbon atoms
of the saturated compounds, to create a double bond between carbon atoms.
1. Dehydration of Alcohols:
Dehydration is removal of water.
Ethene is prepared by heating a mixture of ethanol and excess of concentrated sulphuric acid
at 180°C. In first step, ethyl hydrogen sulphate is formed which decomposes on heating to
produce ethene, which is collected over water.
180 oC
CH3CH2OH + H2SO4 CH3CH2OSO3H + H2O
180 oC
CH3CH2OSO3H CH2 CH2 + H2SO4
2. Dehydrohalogenation of Alkyl Halides:
On heating, ethyl bromide with alcoholic KOH, ethene is formed. Removal of
hydrogen and halogen takes place from adjacent carbon atoms to create a double
bond.
CH3CH2Br + KOH(alcoholic) CH2 CH2 + H2SO4 + H2O
Physical Properties of Alkenes:
1. The first member of the alkenes is ethene. It is a colourless gas with pleasant
odour.
2. Alkenes are nonpolar; therefore, they are insoluble in water but soluble in organic
solvents.
3. The first member of the series ethene is slightly less dense than air.
4. Alkenes are flammable hydrocarbons. On complete combustion, they form carbon
dioxide and water with release of energy. However, their flame is smokier than
alkanes having a similar number of carbon atoms.
 5. Their melting and boiling points gradually increase with the increase of molecular
sizes of the compounds in the series.
Chemical Reactions:
Alkenes are reactive compounds because the electrons of the double bond are easily available
for reaction. These compounds have the tendency to react readily by adding other atoms, to
become saturated compounds. As a result, the double bond is converted into a single bond
that is more stable. Thus, addition reactions are characteristic property of unsaturated
compounds
1. Hydrogenation of Alkenes:
Hydrogenation means addition of molecular hydrogen to an unsaturated hydrocarbon in the
presence of a catalyst (Ni, Pt) to form saturated compound.
CH2 CH2 + H2 Ni
CH3CH3
250-300 oC
On industrial scale, this reaction is used to convert vegetable oil into margarine (Banaspati
ghee).
Ni
Oil + H2 Margarine (Banaspati ghee)
2. Halogenation of Alkenes:
Halogenation means addition of halogen like chlorine or bromine.
Bromination of alkenes is very important reaction . When bromine water (a solution
of bromine in water having red-brown colour) is added to ethene in an inert solvent
like carbon tetrachloride, its colour is discharged at once.
CH2 CH2 + Br2 CH2BrCH2Br
This reaction is used to identify the unsaturation of an organic compound.
3. Hydrohalogenation of Alkenes:
Dry gaseous hydrogen halides (HI, HBr and HC1) react with alkenes to produce alkyl
halides.
CH2 CH2 + HX CH3CH2X
CH2 CH2 + HBr CH3CH2Br
The order of reactivity of hydrogen halides is HI > HBr > HCl
4. Oxidation of Alkenes with KMnO4:
Alkenes decolorize the pink colour of acidified dilute solution of potassium
permanganate because the double bond electrons react with MnO4 - ion, which further
goes on to form MnO2 and ethene glycol (1,2-ethanediol). Such as, there is addition
of two ‘hydroxyl groups’ at the double bond.
3 H2C CH2
3CH2 CH2 + 2KMnO4 + 4H2O + 2MnO2 + 2KOH
OH OH
This reaction is also used to test the unsaturation in an organic compound.
Applications of alkenes:
1. for artificial ripening of fruits;
2. as a general anesthetic;
3. for manufacture of polythene: Polythene is a plastic material used in packaging, toys,
bags, etc.;
 4. as a starting material for the manufacture of many compounds such as ethylene oxide,
ethyl alcohol, ethylene glycol, diethyl ether, etc.; ethylene oxide is used as a fumigant,
ethylene glycol is used as an anti-freeze, diethyl ether and ethyl alcohol are used
5. as solvents
6. for making poisonous mustard gas which is used in chemical warfare.
Alkynes or Acetylenes:
Hydrocarbons containing a carbon-carbon triple (− C  C −) Bond are alkyne. In
common system they are called acetylenes.
The simplest alkyne is acetylene, with molecular formula C2H2. Alkynes are also called
acetylenes because of the name of the first member of the series is acetylene.
General Formula is Cn H2n-2, Where n= 2, 3, 4, …… etc.
Common Names: -
Acetylene and its alkyl derivatives.
IUPAC Names: -
Alkane - ane + yne = Alkyne
The position of the triple bond on the parent chain is designated by lowest possible
Arabic numerals. Some examples are,
Formula Common Name IUPAC Name

CH ≡ CH Acetylene Ethyne

CH3C ≡ CH Methyl acetylene or Allylene Propyne

CH3CH2C ≡1CH Ethyl acetylene But-1-yne

CH3C ≡ 2C1CH
3 Dimethyl acetylene But-2-yne

CH3CH2CH2C ≡1CH3 n-propyl acetylene Pent-1-yne

CH3CH2C ≡2C1CH3 Ethyl methyl Acetylene Pent-2-yne

CH2CH2CH2CH2C ≡1CH n-Butyl acetylene Hex-1-yne

Occurrence:
Acetylene does not occur free in nature. Traces of acetylene are present in coal gas (about
0.06%).
Preparation of Alkynes:
Alkynes are prepared by the following methods.
1. Dehydrohalogenation of Vicinal Dihalides:
When a vicinal dihalide is heated with alcoholic KOH, two hydrogen atoms along with two
halogen atoms are removed from two adjacent carbon atoms with the formation of a triple
bond between the adjacent carbons:
Cl H
100 oC
H C C H + 2KOH(alcoholic) HC CH + 2KCl + 2H2O

H Cl
 2. Dehalogenation of Tetrahalides:
When alkyl tetrahalides are heated with Zinc dust, the elimination of halogen atoms takes
place to form ethyne.
Cl Cl

H + 2Zn(dust) Heat
H C C HC CH + 2ZnCl2

Cl Cl
Physical Properties:
1. Alkynes also form a series of compounds. Its first member is acetylene. It is a
colourless gas with faint garlic odour.
2. Acetylene is slightly soluble in water but soluble in organic solvents such a benzene,
alcohol, acetone, ether, etc.
3. Acetylene is slightly lighter than air.
4. Alkynes are also flammable. They produce smokier flames than those of alkanes and
alkenes.
Chemical Reactions of Alkynes:
Alkynes are reactive compounds because of presence of a triple bond. A triple bond
consists of two weak bonds and a strong bond. When alkynes react with other
substances, two weak bonds are readily broken one by one and addition takes place
easily. The addition reactions of alkynes resemble those of alkenes.
1. Addition of Halogen:
Chlorine and bromine add to acetylene to form tetrachloroethane and tetrabromoethane,
respectively. When bromine water is added to acetylene, red-brown colour of bromine
water is discharged rapidly due to formation of colourless tetrabromoethane.
Br Br

HC CH + 2Br2 H C C H

Br Br
Tetrabromoethane
This reaction is used to identify the unsaturation of alkynes.
2. Oxidation with KMnO4:
Ethyne is oxidized by alkaline KMnO4. And four hydroxyl groups add to the triple bond,
OH OH

HC CH + 2KMnO4 + 2H2O H C C H + 2MnO2 + 2KOH

OH OH
This intermediate product eliminates water molecules to form glyoxal, which is further
oxidized to form oxalic acid.
OH OH O O O O
- 2H2O 2[O]
H C C H H C C H HO C C OH
KMnO4
Oxalic acid
OH OH
Uses of alkynes (Acetylenes)
1. Acetylene produces oxy-acetylene flame with oxygen. It is a highly exothermic
reaction. Heat released is used for welding purposes.
2. Acetylene is used to prepare other chemicals, such as alcohols, acetaldehyde and
acids.
3. It is used for the ripening of fruits.
4. It is used for the manufacturing of polymer products like polyvinyl chloride,
polyvinyl acetate and synthetic rubber like neoprene.
5. It is polymerized to form benzene, which is used as raw material to form a variety
of organic compounds.
Rules of IUPAC Nomenclature of Unsaturated Hydrocarbons: -
While naming compounds containing multiple bonds, the following additional rules are
applied,
i. The parent chain must contain the multiple bonds whether it represents the longest
continuous chain of carbon atom or not.
6 5 4 3
5 4 3 2 1
C C C C C C C C C C
2 1
C C C C

Correct
wrong
ii. If both double and triple bonds are present, the numbering of the parent chain should
always be done from that end which is nearer to the double or triple bond i.e. the lowest
sum for the multiple bonds must be followed.
1 2 3 4 5 6 7 8
C C C C C C C C

Correct (Sum of Locants 2 + 5 = 7)

8 6 5 4 3 2 1
7
C C C C C C C C

Wrong (Sum of Locants = 3+6 = 9)

iii. If there is a choice in numbering the double bond is given preference over the triple bond.
Wrong 1 2 3 4 5
HC C C C C
5 4 3 2 1 Correct
iv. If the organic compound contains only one double or the triple bond. It’s Locants or the
positional number is always placed before its suffix in accordance with 1993
recommendations for IUPAC nomenclature of organic compounds.
H2
H3C 2
C C 4
C CH3
1 H 3H 5

Pent + 2-ene = Pent-2-ene

If both double and triple bond are present, their Locants are written before their
respective suffixes. The terminal “e” from the suffix “ene” is dropped while writing the
complete name of the organic compound. Thus, the organic compound is named as
derivative of alkyne rather than of an alkene.
5 4 3 2 1 6 5 4 3 2 1
H3C C C C CH HC C C C C CH2
H H H H H
Pent + 3 - en(e) + 1 - yne = Pent - 3 - en - 1 - yne Hexa-1,3-dien-5-yne

4 3 2 1 H2C CH3
H2C C C CH2
H 5 4 3 2 1
HC C C C CH
CH3 H

2-Methylbuta-1,3-diene 3-Ethylpenta-1,4-diyne