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Carbon and Its Compounds

Bonding in Carbon

Carbon, a non-metal with atomic number 6 and mass number 12, occurs in
free as well as in combined form. All living creatures are based on it. Its amount in
the earths crust and in the atmosphere is quite meagre. In earths crust, there is
only 0.02% carbon which is present as minerals and in the atmosphere 0.03%
carbon is present in the form of carbon dioxide. Carbon thus forms a large
number of compounds with itself and with the atoms of other elements; some of
which are studied in this chapter.

Bonding in Carbon Compounds :

The Covalent Bond

Atomic number of carbon is 6, so there are 4 electrons in its outermost shell


and it needs to gain or loss 4 electrons in order to attain a stable configuration,
i.e., noble gas configuration.
The octet can be completed by following two ways
4+
(i) It could lose 4 electrons and form C
cation. But a massive amount of
energy is required to remove 4 electrons leaving behind a carbon cation
with 6 protons in its nucleus holding on to just two electrons.
4
(ii) It could gain 4 electrons and can form C anion. But for a nucleus having
6 protons, it would be difficult to hold on to 10 electrons, i.e., 4 extra
electrons.

In order to overcome this problem, carbon shares its valence electrons with its
other atoms or atoms of other elements.
These shared electrons belong to the outer shells of both the atoms and in this
way, both atoms attain the noble gas configuration. This type of bonding is called
covalent bonding. Thus, the bonds which are formed by the sharing of an electron
pair between two same or different atoms are known as covalent bonds.

Compounds: The Covalent


Bond
Allotropes of Carbon
Versatile Nature of
Carbon
Organic Compounds
Hydrocarbons
Functional Groups
Nomenclature of Carbon
Compounds
Chemical Properties of
Carbon Compounds
Fuels and Flames
Some Important Carbon
Compounds
Soaps and Detergents

2
Shared electrons

The number of electrons shared show the covalency of that


atom. Other atoms also exhibit similar type of bonding.

Examples

O==O

Oxygen molecule

Oxygen atoms

(i) Formation of Hydrogen Molecule

Covalent bonding in O2 molecule

Atomic number of H = 1
It has 1 electron in its K shell and needs 1 more electron
to fill the K shell completely.
Thus, 2 H atoms share each of their electron to form a
molecule of H 2 and thus, each H atom attains the nearest
noble gas configuration of helium (having two electrons
in its K shell). Valence electrons are depicted by using
dots or crosses.

Here, a double bond between two oxygen atoms


forming an oxygen molecule represents the sharing of
4 electrons.

(iv) Formation of Nitrogen Molecule


Atomic number of N = 7
K L

Electronic configuration = 2 , 5
It needs 3 more electrons to attain noble gas
configuration. Thus, 2 nitrogen atoms share 3 each of
their electrons, forming a triple bond of nitrogen
molecule.

H
Hydrogen atoms
Shared electrons
H2 molecule

Shared electrons

The shared pair of electrons constitute a single bond


between the two H-atoms, which is represented by a
single line between the two atoms.

(v) Formation of Methane


Molecular formula CH4
In methane molecule formation, one carbon shares 4
electrons with four different hydrogen atoms (one each
of different hydrogen atoms).
It shows carbon is tetravalent because it possesses four
valence electrons and hydrogen is monovalent because it
has only one valence electron.

(ii) Formation of Chlorine Molecule


L M

Electronic configuration = 2 , 8, 7

It has 7 electrons in its outermost shell and thus requires


1 more electron to fulfill its outermost shell. This is
achieved by sharing of 1 electron with another Cl atom,
forming a chlorine molecule (Cl 2 ).

H
H

Shared electrons

H
H

HCH
H

H
Cl

Cl

Chlorine atoms

Cl

NN

Covalent bonding in N2 molecule

Single bond showing H2 molecule

Nitrogen molecule

Nitrogen atoms

or HH

Atomic number of Cl = 17

Cl

ClCl

Chlorine
molecule

Covalent bonding in Cl2 molecule

(iii) Formation of Oxygen Molecule


Atomic number of O = 8

Formation of methane (CH4 ) molecule

Methane is a carbon compound and also called marsh gas It is


used as a fuel and a major component of CNG (Compressed
Natural Gas) and biogas.

(vi) Formation of Ammonia and Water Molecule


Ammonia (NH3 )

K L

Electronic configuration = 2 , 6

It requires 2 electrons to fulfill its octet and attain noble


gas configuration. This is achieved by sharing of 2
electrons of an another oxygen atom.

NH

Ammonia (NH3 ) molecule

Water (H2O)
H

H
HOH

or O
H

Allotropes of Carbon

Water (H2O) molecule

(vii) Formation of Carbon Dioxide (CO2)

Some chemical elements can exist in two or more


different forms, which differ in arrangement of atoms and in
number of atoms but are chemically same. These are known
as allotropes and this phenomenon is known as allotropism.

Atomic number of C = 6
KL

Electronic configuration = 2 4

For example, Carbon exists in several allotropic forms like


diamond, graphite, buckminster fullerene, coal, charcoal,
etc. The former three are crystalline while others are
amorphous form.

Atomic number of O = 8
KL

Electronic configuration = 2 6
Thus, they complete their octet as

O == C ==O

or

(viii) Formation of Sulphur Molecule (S8)


Atomic number of sulphur = 16
K L M

Electronic configuration = 2 8 6
So, the valency of each S atom is 2.
S

S
S

are the bad conductors of electricity due to the absence


of free electrons or ions. However, graphite is an
exception of it, which is a good conductor of electricity.
These compounds are generally insoluble in water but
some which are capable to form H-bond are soluble in
water.

S
Crown shaped
S8 molecule

Properties of Covalent Compounds


Covalently bonded molecules are called covalent
compounds.
Their important properties are

Their constituents are molecules, not ions.

They have strong bonds within the molecule but


intermolecular forces are weak, which is responsible for
the low melting and boiling points of these compounds
(graphite and diamond are exceptions of this).

In these compounds, electrons are only shared and no


charged particle is formed, therefore, these compounds

Diamond
General Properties
General properties of diamond are

It is a colourless transparent substance with


extraordinary brilliance due to its high refractive index.

It is quite heavy.

It is extremely hard (hardest natural substance known).

It does not conduct electricity (because of the absence of


free electrons).

It has high thermal conductivity and high melting


point.

It burns on strong heating to form carbon dioxide.


Structure
It is a giant molecule of carbon atoms in which each
carbon atom is linked to four other carbon atoms by strong
covalent bonds forming a rigid three-dimensional network
structure, which is responsible for its hardness. Moreover, a
lot of energy is required to break the network of strong
covalent bonds in the diamond crystal, thus its melting
point is very high.

Diamond structure

Uses
Uses of diamond are

Due to its hardness it is used in knives for cutting marble,


granite and glass.

It is used for the purpose of ornaments studded as precious


stones.

It is used as an abrasive and for polishing hard surface.

Dies made from diamond are used for drawing wires from
the metals.

Diamond can be prepared artificially by subjecting pure carbon to


very high pressure and temperature. These synthetic diamonds are
small but are otherwise indistinguishable from natural diamonds.

Graphite
General Properties
General properties of graphite are

It is a greyish black opaque substance.

It is lighter than diamond, feels soft and slippery to touch.

It is a good conductor of electricity (due to the presence of


free electrons) but bad conductor of heat.

It burns on strong heating to form carbon dioxide.


Structure
A graphite crystal consists of layers of carbon atoms or
sheets of carbon atoms. Each carbon atom in a graphite layer is
joined to three other carbon atoms by strong covalent bonds to
form flat hexagonal rings. However, the fourth electron of each
carbon atom is free which makes it good conductor of
electricity. The various layers of carbon atoms in graphite are
held together by weak van der Waals forces so these can slide
over one another.

Fullerenes
These are recently prepared allotropic forms of carbon
and were prepared first time by HW Kroto, Smalley and
Robert Curt by the action of laser beam on the vapours of
graphite. Most commonly known fullerene contains 60 C
atoms (C60 ) with smaller proportion of C 70 and traces of
compounds containing even upto 370 carbon atoms.
C60 fullerene was named buckminsterfullerene after
the American architect Buckminster Fuller because its
structure resembled with the framework of domeshaped
halls designed by Fuller for the large international
exhibitions.
Properties
Properties of fullerenes are

These are dark solids at room temperature.

These are neither too hard nor too soft.

These are the purest allotrophic forms of carbon


because of the absence of free valencies or surface
bonds.

On burning, these produce only carbon dioxide gas.


Other properties of fullerene are still being
investigated.
Structure
C 60 is a football shaped spherical molecule in
which 60 C atoms are arranged in interlocking hexagonal
and pentagonal rings of carbon atoms. One C 60 molecule
contains 20 hexagons and 12 pentagons of carbon atoms.

Graphite Structure

Uses
Uses of graphite are

It is used as a powdered lubricant for the parts of


machinery.

It is used for making electrodes of cells.

It is used for making lead for pencils as it can mark paper


black. It is therefore called black lead or plumbago.

It can withstand high temperature so used for making


crucibles to melt substances with high melting points and
tiles on the nose cone of space shuttle.

Buckminster fullerene (C60 ) Structure

Uses
Uses of fullerene are

In pure form, these behave as insulators. However,


these can be converted into semiconductors under
suitable conditions.
C O, a molecule formed when C
60
60 traps O atoms, is
used in cancer as well as AIDS therapy.

In small amounts, these are used to catalyse the


photochemical refining in industry.

Check

oint

1. What is the covalency of nitrogen atom in nitrogen

gas?
2. Name the two properties of carbon which makes it
different from other elements.
3. Why are covalent compounds bad conductor of
electricity?
4. Graphite is a covalent molecule but a good
conductor of electricity. Explain why?
5. Why are fullerene so called?

Versatile Nature of Carbon


The estimate number of carbon compounds known
today is about three million. But now the question is, which
property or properties of carbon is/are responsible for the
formation of such a large number of carbon compounds.
Two characteristic properties of carbon are responsible
for this.
These properties are
(i) Catenation (ii) Tetravalency

(i) Catenation
Carbon atoms have a unique ability to form bonds
(single, double as well as triple) with other carbon atoms to
form large molecules. These can arrange themselves in
straight chain, in branched chains or in the form of rings.
This property of self linking of carbons atom through
covalent bonds to form straight chains or cyclic rings of
carbon atoms is called catenation.
Carbon exhibits the property of catenation to maximum
extent due to large C-C bond energy and hence, forms large
number of compounds.

(ii) Tetravalency
Due to the valency of four, carbon is capable of bonding
or pairing with four other carbon atoms or with the atoms of

some other monovalent elements. It also forms compounds


with oxygen, nitrogen, sulphur, hydrogen and many other
elements. This gives rise to compounds with specific
properties which depend on the element other than carbon
present in the molecule.
Bonds which carbon forms with other elements are very
strong thus, making these compounds very stable. The main
reason for such strong bond formation is the small size of
carbon. As a result, the shared pair of electrons are tightly
held by the nucleus.

The strength of bond decreases with increase in the size of


atoms.

Organic Compounds
The compounds of carbon except its oxides, carbonates
and hydrogen carbonate salts, are known as organic
compounds. These compounds were initially extracted from
natural substances and was believed that some vital force was
necessary for the synthesis of these compounds (vital force
theory).
In 1828, synthesis of urea, by German chemist Friedrich
Wohler accidently when he was trying to prepare
ammonium cyanate by heating ammonium sulphate and
potassium cyanate, gave death below to this theory.
(NH4 ) 2 SO4
Ammonium sulphate

2KCNO

Potassium cyanate

2NH4 CNO + K 2 SO 4
Ammonium
cyanate

Potassium
sulphate

NH4 CNO (Rearrangement) NH2CONH2


Ammonium
cyanate

Urea

Synthesis of acetic acid from its elements by Kolbe in


1845 also disproved the vital force theory.

Classification of Organic Compounds


Organic compounds are classified into following manner
Organic Compounds

(compounds of carbon
except oxides, carbonates
and bicarbonates)

Close Chain or Cyclic


Compounds (have carbon
atoms arranged in rings)

Open Chain Compounds


(have open chain of C-atom)

Hydrocarbon Derivatives
(compounds obtained by replacing
one or more H of hydrocarbons by
any other atom or groups of atoms)
e.g., CH3Cl (methyl chloride),
CH3OH (methanol), etc.)

Hydrocarbons
(compounds having
carbon and hydrogen only)

Saturated
(having only single bonds)
e.g., C2H6 (ethane)
H H
H

H, CH4 (methane)
H
H

Homocyclic
(have cycle of
only C atoms)

Alicyclic
(does not have
benzene ring)
e.g., CH
2

CH2
H2C
(Cyclopropane)

Heterocyclic
(have atleast one atom
other than carbon as a
part of the ring).

Aromatic
(have benzene ring)
e.g.,

C C H (furan)
O

(benzene)
CH3 (toluene)

H
Unsaturated
(having atleast one double or
triple bond alongwith single bonds)

Alkenes
(have atleast one
double bond)
e.g., ethene (C2H4)
H
H
C C
H
H

Alkynes
(have atleast
one triple bond)
e.g., ethyne (C2H2)
H C C H

Hydrocarbons
All the carbon compounds which contain only carbon
and hydrogen are called hydrocarbons. Their main sources
are petroleum (or crude oil) and natural gas.
On the basis of types of bond present (only single or
double or triple bond alongwith single bonds),
hydrocarbons are divided into two classes.

Saturated Hydrocarbons
The hydrocarbons in which all the carbon atoms are
connected by only single bonds are called saturated
hydrocarbons or alkanes or paraffins.

The general formula of these compounds is Cn H2n + 2 ,


where, n = number of carbon atoms in one molecule of a
hydrocarbon.
For example, if there is only one carbon atom then its
formula should be C1H2 1+2 = CH4 (methane).
Similarly, if there are two carbon atoms in the saturated
hydrocarbon (alkane), its formula must be C 2H2 2 + 2
= C 2H6 (ethane)
These compounds are chemically inert (i.e., less reactive)
and burn with blue flame due to their complete combustion.
These compounds generally show substitution reaction
(which are discussed later in this chapter).

Unsaturated Hydrocarbons
Those carbon compounds in which atleast one double or
triple bond (or multiple bond) is present alongwith single
bonds, are called unsaturated compounds.
These compounds generally burn with sooty flame due
to their incomplete combustion. These are highly reactive
and generally undergo addition reaction (which are
discussed later in the chapter).
Unsaturated compounds further divided into following two
classes
(i) Alkenes or Oleffins
Those carbon compounds which have atleast one double
bond alongwith single bonds are called alkenes. (A double
bond is formed by the sharing of two pairs of electrons
between the two carbon atoms).
General formula of these compounds is Cn H2n .
For example, if an alkene have two carbon atoms, its
formula is C 2H22 = C 2H4 (ethane).
(ii) Alkynes
Those unsaturated hydrocarbons which have one or
more triple bonds alongwith the single bonds are called
alkynes. (A triple bond is formed by the sharing of three
pairs of electrons between two carbon atoms).
General formula of these compounds is Cn H2n 2 .
For example, if an alkyne have two carbon atoms then its
formula is C 2H222 = C 2H2 (ethyne). If there are 3 carbon
atoms in the alkyne then its formula must be
C3 H23 2 = C3 H 4 .

The minimum number of carbon atoms present in an unsaturated


compound is 2 because formation of double or triple bonds is
possible only then.

How to Draw the Structure of Saturated


and Unsaturated Compounds?
To draw the structure of carbon compound, first
connect all the carbon atoms by a single bond.
Step 2 After that satisfy the tetravalency of carbon with
available hydrogen atom.
Step 3 If number of available H-atoms are less than that
required, satisfy the remaining valency by using
double or triple bond.
Step 1

(i) Structure of Ethane (C 2H6)


CC

[I step]

Here only one valency of carbon is satisfied and the three


remains unsatisfied.

Each of these unsatisfied valencies are satisfied by


hydrogen atoms.
H H

H C C H
[II step]

H H
Now, the tetravalency of carbon in ethane is satisfied.
Electron dot structure of ethane (C 2H 6 )

(ii) Structure of Propane (C3H8 )


Same rules are followed as in case of ethane.
CCC
[I step]
Carbon atoms linked together with a single bond.
H H H

[II step]
H C C C H

H H H
Two C-atoms are bonded to 3 hydrogen atoms and one
carbon atom is bonded to 2 hydrogen atoms.
Electron dot structure of propane

(iii) Structure of Ethene (C 2H4 )


CC
H
H

CC

[I step]
H
[II step]
H

But in this case, even after linking the hydrogen atoms


with carbon atoms, still one valency of each carbon remain
unsatisfied. To satisfy it, a double bond is used between the
two carbon atoms.
H
H
C==C
[III step]
H
H
Now, all the four valencies of carbon are satisfied.

Electron dot structure of ethene


H

Isomerism

H
C

(iii) Structure of Ethyne (C 2H2 )


CC
[Step I]
[Step
II
and III]
HC CH
In ethyne, the two carbon atoms share three pairs of
electrons among themselves to form a carbon-carbon triple
bond. Each carbon atom shares one electron with each
hydrogen atom to form two carbon-hydrogen single bonds.
Electron dot structure of ethyne

Carbon compounds or organic compounds with same


molecular formula can show different structures and hence,
different properties. This phenomenon is called isomerism
and compounds are called isomers.
For example, following two arrangements are possible
for butane, an alkane with four C atoms (C 4 H10 )
H H H H

H C C C C H

H H H H
Straight chain structure

H
H

H C

H H

How to Draw Structure of Cyclic


Compounds ?
Some carbon compounds also exist in cyclic or ring
structure.
To draw the structure of cyclic or ring compounds
Step 1 First connect the available carbon atoms by a single
bond in the cyclic form.
Step 2 Try to satisfy the tetravalancy of each carbon with
the available hydrogen atoms.
Step 3 Now check the valency of each carbon. If it is found
unsatisfied, use double or triple bond to satisfy it.

H H H H
CC

CC

or

HC
H

C
C

Such pair of isomers is called chain isomers and the


isomerism is called chain isomerism. Thus, chain isomers are
the compounds that have same molecular formula but differ
in the arrangement of carbon chains.
Further, if we draw the structure of an alkane with 4
carbon atoms, the following two arrangements are possible
H
H
H H
H
4

H C C C C

H and H C C C C

H H H

H H H

or

Chain and position isomerism is possible only when, atleast


4 carbon atoms are present in the hydrocarbons.

Functional Groups

Benzene (C 6H6 )

Branched chain structure

H
H

H H H H

The above two structures differ in the position of double


bond (functional group), so these are called position isomers
and the phenomenon is called position isomerism.

Examples
Cyclohexane (C 6H12 )

H
H

H
H
H

or

Carbon can also form bonds with other elements such


halogens, oxygen, nitrogen, sulphur, etc. These are called
hetero atoms. These atoms or the groups containing these,
replace one or more hydrogen atoms of the hydrocarbon and
are responsible for the chemical reactivity of the compound,
regardless of the length and nature of carbon chain. Hence,
these are called functional groups.

Some important functional groups are tabulated below


Representation of Different Functional Groups
Functional group
OH
H

C ==O
O

C
O

C ==OH

Representation
with alkyl group

Family
Alcohols
Aldehydes
Ketone

Carboxylic acids

ROH
O

R C H
O

R C R
O

R C OH

NH2
O

Amines
Ethers

RNH2
ROR

X
NO2

Halogen
Nitro group

RX
RNO2

Nomenclature of Carbon Compounds


In general, the names of organic compounds are based on
the name of basic carbon chain modified by a prefix (phrase
before) or suffix (phrase after) showing the name of the
functional group.
Following steps are used to write the name of an organic
compound
Step 1 Count the number of carbon atoms in the given
compound and write the root word for it (Root
word upto 10 carbon atoms are tabulated below.)
Root Words for Carbon Atoms
No. of
C atoms

Free valency or valencies of the functional group are shown by


the single line.

The formula of a particular family is made up of two


parts. These are alkyl group and functional group linked to
each other by covalent bond. For example,
OH
CH3
Methanol or methyl alcohol
14243 1442443
alkyl group

Step 2

functional group

Similarly,
CH3 C CH3 Propanone
14243
14243
Alkyl group

Alkyl group

or dimethyl ketone

Homologous Series
A series of compounds in which hydrogen in a carbon
chain is replaced by the same functional group, is called
homologous series.
Characteristics of a Homologous Series

All the members of a homologous series can


be
represented by the same general formulae.

Any two adjacent homologues differ by 1 carbon atom


and 2 hydrogen atoms in their molecular formulae.

All the compounds of a homologous series show similar


chemical properties.

With increase in the molecular mass the gradual change


in the physical properties occurs.

The 14 u is the difference in the molecular masses of any


two adjacent homologues.
For example,
CH4 , C 2H6 , C3 H 8 , C 4 H10 these all compounds
differ by a CH 2 unit.

Step 3

Root word

No. of
C atoms

Root
word

(C )

Meth

(C

(C )

Eth

(C )

Hept

(C3 )

Prop

(C8 )

Oct

(C4 )

But

(C9 )

Non

(C5 )

Pent

10 (C10 )

Dec

Hex

If the compound is saturated, add suffix ane to the


root word, but if is unsaturated, add suffix ene and
yne for double and triple bonds respectively.
For example, CH3 CH2CH3 contains three C atoms
so root word is prop and it contains only single
bonds, so suffix used is ane. Hence, the name of
this compound is propane.
Similarly, the compound CH3 CH == CH2 is
named as propene as here suffix ene is used for
double bond.
If functional group is present in the compound, it is
indicated by adding its suffix (which are given in
the table below).

Prefix and Suffix of Different Functional Groups


Functional
Group

Prefix/Suffix

Example

Alcohol

Suffix -ol

C3H7 OH Proanee+ol
Propanol

Aldehyde

Suffix -al

CH3CHO Ethanee+al=
Ethanal

Ketone

Suffix -one

CH3COCH3 - Propanee+one
Propanone

Carboxylic
acid

Suffix -oic acid

CH3COOH - Acetic acid/


Ethanoic acid

Halogen

Prefix -chloro,
bromo, etc.

CH3Cl - Chloromethane
C2H5Br - Bromoethane

10

Functional
Group

Prefix/Suffix

Double bond
(alkenes)

Triple bond

Suffix -ene

Example
H H

H
HC C==C

H
H
- Propene
H

Suffix -yne

(alkynes)

HC
CC H
H
- Propyne

Prefix iso and neorepresent the presence of one


or two carbon atoms respectively as side chain.
If the functional group is named as a suffix, the final
e of alkane (or alkene or alkyne) is substituted by
appropriate suffix.
If the functional group and subtituents are not
present at first carbon, then their location is
indicated by digits 1,2,3... .

Check

oint

1. Draw the electron dot structure of

Chemical Properties of Carbon Compounds


Combustion

All the carbon compounds burn in oxygen and yield carbon dioxide

and water vapour. Heat and light are also released during this process.
This reaction is called combustion.
CH4 + 2 O 2 CO2 + 2H2O + Heat + Light
Further, once carbon and its compounds ignite, they keep on burning
without the requirement of additional energy. Thats why these
compounds are used as fuels.
Saturated hydrocarbons give a clean flame due to their complete
combustion whereas, unsaturated hydrocarbons give a yellow flame with
lots of black smoke as they do not undergo complete combustion.

Oxidation
Oxidation is a process of intake of oxygen and removal of
hydrogen. Reagents used for this purpose are alkaline KMnO4 + heat or
acidified K 2Cr2O7 + heat.
For example,
O
Alkaline KMnO4
+ heat

CH3 CH2OH + [O] CH3 C OH


or Acidified K Cr O

propene (C3H6 ).

2. What is the formula of an alkyne

having five carbon atoms?

3. Draw all the isomers of pentane

ethanol

+ heat

2 7

acetic acid
(ethanoic acid)

Substances that are capable of providing oxygen to other substances


are called oxidising agents.
In general,

(C 5H12 ).

[O]

[O]

Alcohol Aldehyde Acid.

4. Name the following compounds

Addition Reactions

5. Write the name of the functional

The reaction in which a reagent adds completely on a substance


without the removal of small molecules are called addition reactions.
For example, addition of hydrogen (in the presence of catalysts like
Palladium or Nickel) to unsaturated hydrocarbons, yields saturated
hydrocarbons (Hydrogenation).
H H
R
R Nickel catalyst

C==C
R C C R
H2 , 200 C
R
R

R R

according to IUPAC.
(i) CH3CH2CH2COOH
H

(ii) H C C ==O

H H
(iii) CH3 OH

group present in the following


compounds.
(i) CH3OH
Cl

(ii) CH3 C HCH3


(iii) Ethanal
(iv) Acetic acid
(v) Hexyne

Hydrogenation (addition of hydrogen) of vegetable oil (which are


unsaturated compounds) in the presence of nickel catalyst gives ghee
(saturated compounds). This process is called hardening of oils.
Vegetables oils Ni
catalyst
Ghee
H2 200C
A catalyst is that substance which alters the rate of a reaction without being
consumed.
Saturated fatty acids are harmful for health.
Unsaturated compound discharge the pink colour of alkaline KMn04 . This is
known as test of unsaturation.

Substitution Reactions

Flame

The reactions in which a reagent substitutes (replaces) an atom


or a group of atoms from the reactant (substrate) are called
substitution reactions. These are generally shown by saturated
compounds and benzene.

A flame is the region where combustion


(or burning) of gaseous substances takes place.
Depending upon the amount of oxygen available
and burning of fuels, flames are of following two types

Most of the saturated hydrocarbons are fairly inert and


unreactive in the presence of most reagents. So, presence of sunlight
is necessary for their substitution reactions.
When chlorine is added to hydrocarbons at a rapid rate, in the
presence of sunlight, Cl replaces H atom one by one.
sunlight

CH4 + Cl 2 CH3 Cl + HCl


sunlight

CH3 Cl + Cl 2 CH2Cl 2 + HCl


sunlight

CH2Cl 2 + Cl 2 CHCl3 + HCl


CHCl3 + Cl 2

sunlight

CCl 4 + HCl

Fuels and Flames


Fuels
Those carbon compounds which have stored energy in them and
burn with heat and light are called fuels. The released energy (heat or
light) is utilised for various purposes like for cooking food, running
machines in factories, etc.
In fuels, the carbon can be in free state as present in coal, coke
and charcoal or in combined state as present in petrol, LPG,
kerosene, petroleum, natural gas, etc.
Those fuels which were formed by the decomposition of the
remains of the pre-historic plants and animals (fossils) burried under
the earth long ago, are called fossils fuels.
For example, coal, petroleum and natural gas.
Coal
It is a complex mixture of compounds of carbon, hydrogen and
oxygen and some free carbon alongwith traces of nitrogen and
sulphur.
It was formed by the decomposition of plants and trees buried
under the earth millions of years ago.
Petroleum
It is a dark viscous foul smelling oil and is also known as rock oil
or black gold. It was formed by the decomposition of the remains of
extremely small plants and animals buried under the sea millions of
years ago.

Since coal and petroleum have nitrogen and sulphur in small amounts
thats why they play an important role in causing pollution (air pollution).

(i) Blue or Non-luminous Flame


When the oxygen supply is sufficient, the fuels
burn completely producing a blue flame. Since, light
is not produced during this type of combustion, so
the flame is called non-luminous (non-light giving
flame), e.g., burning of LPG in gas stove.
(ii) Yellow or Luminous Flame
In the insufficient supply of air, the fuels burn
incompletely and produce yellow flame. The colour
of the flame is yellow because of the presence of
unburnt carbon particles. This flame produces light
so also known as luminous flame. e.g., burning of
wax vapours.

Some solid and liquid fuels like coal and charcoal do not
vaporise on heating. Such fuels burn without producing
a flame. They just glow red and give out heat.

Some Important Carbon


Compounds
Ethanol
Its common name is ethyl alcohol and formula is
C 2H5 OH.
H H

H C C OH

H H
Preparation
Alcohol (ethanol) is obtained by the
fermentation of molasses which are obtained from
sugarcane juice.
yeast

Sugar Molasses
Ethanol.
Physical Properties
Physical properties of ethanol are

It is a liquid at room temperature. Its melting


point is 156 K and boiling point is 351 K.

It is soluble in water due to its ability to form


H-bonds with water molecules.

(ii) Esterification When ethanol (an alcohol) reacts with

Chemical Reactions
(i) With sodium Hydrogen is evolved

acetic acid (a carboxylic acid), a fruity (sweet)


smelling liquid called ester, is obtained. This reaction

2Na + 2CH3 CH2OH 2CH3 CH2O Na + H 2

Sodium

is called esterification.

(Sodium ethoxide)

Acid

(ii) Dehydration (Removal of water) it is done by

conc.H2 SO 4 .

CH3 COOH + CH3 CH2OH


Ethanoic
acid

hot concentrated

CH3 CH2OH CH2 ==CH2 + H2O


Ethanol

H2SO4
160C

CH3 C OCH 2 CH 3

Ethene

Uses
Uses of ethanol are

It is used as active ingredients in all alcoholic drinks.

It is useful in medicines like tincture of iodine, cough


syrups and many other tonics.

Alcohol is used as an additive in petrol, since it is a


cleaner fuel and gives rise to only CO2 and H2O.

It is used as hypnotic (induces sleep).

It is used for the preparation of chloroform, iodoform,


ethanoic acid, ethanal, etc.

H 2 O

Ethanol

Ester

The ester gets converted back into alcohol and sodium


salt of acid when treated with alkali like sodium hydroxide.
This reaction is called saponification, as it is used for the
preparation of soap.
NaOH

CH3 COOC 2H5 C 2H5 OH + CH3 COONa


Ethyl acetate

Ethyl alcohol

Sodium acetate

(iii) Reaction with carbonates and hydrogen carbonates

Carbon dioxide gas is obtained. It is an example of


acid base reaction.
CH3 COOH + NaHCO3 CH3 COONa

Harmful Effects of Drinking

+ H2O + CO2
2CH3 COOH + Na 2CO3 2CH COONa
3
+ H2O + CO2
(iv) Reaction with a base
CH3 COOH + NaOH CH3 COONa + H2O

Ethanoic Acid or Acetic Acid


It is commonly known as acetic acid. Its formula is
CH3 COOH. 58% solution of ethanoic acid in water is
known as vinegar.
Physical Properties
Physical properties of ethanoic acid are

Its melting point is 290 K.

During winters in cold climates it often freezes and


forms ice like flakes so it is also called glacial acetic acid.
Chemical Reactions
(i) Acidity It is a weaker acid than HCl but stronger
than alcohol. It evolves hydrogen with sodium
metal, which shows its acidic nature.
2CH3 COOH + 2Na 2CH3 COONa + H 2

Esters are used in making perfumes and as flavouring agents.

Uses of Acetic Acid


(i) It is used for making vinegar.
(ii) It is used in making pickles.
(iii) It is used for the synthesis of other compounds like
esters.

Soaps and Detergents


Soaps are sodium or potassium salts of long chain
carboxylic acids and have general formula RCOONa.
where,
R = C15 H31 , C17 H35 , etc.
C15 H31COOH is called palmitic acid.
Detergents are usually ammonium or sulphonate salts of
long chain carboxylic acids.
Manufacture of Soap and Detergents
Soaps are made from animal fat or vegetable oils by
heating it with sodium hydroxide.

Fat or Oil + Alkali


(Ester)

Heat

(Sodium
hydroxide)

+ Glycerol

Soap
Sodium
(Salt of fatty acid)

(An alcohol)

ion-ion repulsion. Hence, the dirt suspended in the


micelles is also easily rinsed away.
Hydrophilic end hydrophilic end Hydrophobic end
hydrophobic end
Soap molecule
Na+
Na+
Grease
dirt

This process of preparation of soap by the fats and oil


hydrolysis with alkalies is called saponification.
In case of detergents, the long chain hydrocarbons obtained
from petroleum is taken instead of fat or oil.

Na+ Water

In the soap manufacturing, common salt is added to precipitate soap.

Structure of a Soap Molecule


A soap molecule is made up of two partsa long hydrocarbon
part and a short ionic part containing COONa group. The long
hydrocarbon part is hydrophobic and therefore insoluble in water
but soluble in oil. The ionic portion of the soap molecule is
hydrophilic so soluble in water and insoluble in oil.
Hydrophobic

Hydrophilic

part (Tail)

part (Head)
Hydrophilic
Heads

Dirt and bacteria


trapped in the center

Hydrophobic
tails

The Soap Micelle

Cleaning Action of Soaps (Micelle Formation)


Soap molecules have different properties at their two ends,
one is hydrophilic (soluble in water) and other is hydrophobic
(soluble in fats or oils).
At the surface of water, the hydrophobic end or tail of soap
will be insoluble in water and the soap will lie along the surface of
water with the ionic end in water and the hydrocarbon tail
protruding out of water.
Inside water, these molecules show a unique orientation that
keeps the hydrocarbon portion out of the water. This is done by
forming clusters of molecules in which the hydrophobic tails are
in the interior of the cluster and on the surface of cluster, ionic
ends are present. This formation is called micelle formation. To
wash away the loosened dirt particles in the form of micelles from
the surface of the cloth, it is either scrubbed mechanically or
beaten or agitated in washing machine.
In the form of a micelle, soap is able to clean, since the oily dirt
is being collected in the centre of micelle. Micelles stays as colloids
in the solution and does not come closer to precipitate due to

Cleaning Action of Soap (Micelle formation)

Soap forms scum with hard water as it reacts with


calcium and magnesium ions present in the hard water.
2RCOONa+ Mg 2+ (RCOO) 2 Mg+ 2Na +
From hard
water

Scum

Here,
R = C17 H35 or C15 H31
Charged ends of detergents do not form insoluble
precipitates withthe magnesiumandcalciumions inwater.
Hence, they are effective in hard water. Thus, detergents
are used as cleansing agents in case of hard water.
Detergents are useful in making shampoos and
products for cleaning clothes but their main disadvantage
is that these are generally non-biodegradable.
Advantages of Detergents Over Soaps

Synthetic detergents do not require vegetable oil or


fats for their preparation, hence they help in saving
oils and fats for human consumption.

Synthetic detergents can be used with hard water


while soaps cannot be used with hard water.

Soap solution appears cloudy because the soap micelles are


large enough to scatter light.

Check

oint

1. Which metal is used as a catalyst in the


2.
3.
4.
5.

conversion of vegetable oil into fat (ghee)?


Why is sunlight necessary for the substitution
reactions of alkanes?
Why are esters used in perfume industry?
What is the product formed when acetic acid
reacts with alcohol?
Write the chemical reactions of soap formation
or saponification.

ll

ne

Answers for Check Points


Check Point
1.

2.
3.
4.

(i) Catenation

5.

H
(ii) Tetravalency

Because of the resemblance with framework of domeshaped


halls designed by the American architect Buckminster Fuller.

If n = 5
The formula of alkyne is C5H2 5 2 = C5H10 2 = C5H8 .

n-pentane

H H
H
H

(ii) HC C C C H

H H
H
HC H

H
iso -pentane or 2 -methylbutane

CH
H

H
2,2-dimethyl propane or neo-pentane

4.

(i) Butanoic acid


(ii) Ethanal
(iii) Methanol

5.

(i) Alcohol
(ii) Chloro
(iii) Aldehyde
(iv) Carboxylic acid
(v) Triple bond (alkyne).

2. General formula of alkynes is C nH 2 n 2 .

The isomers of pentane are as


H H H H
H

(i) HC C C C C H

H H H H
H

H
H

HC

Although graphite is a covalent molecule but its each carbon


atom utilise only three electrons for bonding and the fourth
electron of each carbon atom is free which makes it good
conductor of electricity.

Check Point

Because of the absence of free ions or electrons.

1.

3.

(iii)

Check Point
1.
2.

Nickel

3.
4.

Because of their sweet smell.

5.

Because these are inert and sunlight generates free radicals


which readily attacks on alkanes.

Ester
CH2COOR
CH2OH

CHCOOR + 3NaOH 3RCOONa + CHOH


Soap

CH2COOR
CH2OH

1. Q. What happen when few drops of alkaline KMnO4 added to Ethanol?


Ans: In the beginning, colour of KMnO4 disappears. When excess KMnO4 is dissolved in solution
colour cannot disappear because whole Ethanol gets oxidized into Ethanoic acid.
CH3CH2OH

---- KMnO4------Heat------->

CH3COOH

Hence, alkaline KMnO4 or Acidified K2Cr2O7 oxidized alcohol into ethanoic acid
Ethanol is highly inflammable and catches fire readily. This is why during oxidation it should never
be heat directly on a burner. It should be heated on a water bath
2. Q. How can we convert unsaturated hydrocarbon into saturated hydrocarbon?
Ans: By the addition reaction of unsaturated hydrocarbon with halo atom in the presence of catalyst.
HC=CH +H2 -------------Ni--------5700 K------> Ch3-CH3
R2C=CR2 + H2

------------Ni---------> R2HC-CHR2 (Vegetable Gee)

This reaction is known as Hydrogenation reaction.


3. Q. How can you test that given hydrocarbon is unsaturated?
Ans: When few drops of Bromine is added to unsaturated hydrocarbon its colour disappear due to
addition reaction.
For example: If drops of bromine water added to ethyne, the reddish brown colour of Bromine
disappear due to addition reaction.
HCCH + Br2 -------------> HBr2 C CHBr2 (Tetra Bromo ethane is formed)
4. Q. How can you prepare alkenes from Ethanol?
Ans: When Ethanol heated in presence of Conc.H2SO4 or Al2O3 at 623 degree C ,Ethanol loose
water molecules and form alkenes. C2H5OH ---H2SO4------623C------>CH2=CH2 + H2O
5. Q. What happen when a piece of sodium metal added to Ethanol?
Ans: Sodium ethoxide is formed with evolution of H2 gas
C2H5OH

+ Na -------------> C2H5ONa + H2

6. Q. What happens when few drops of Conc.H2SO4 is added to Solution of Ethanoic acid and
Ethanol?
Ans: A substance with fruity smell is formed called Ester.This reaction is known as Esterification
C2H5OH + CH3COOH ------H2SO4------> CH3COO C2H5 (Ester or, Ethyl Ethanoate)
7. Q. What types of flame produce by burning of Benzene, Nepthline and Camphor?
Ans: Smoky flame due presence of excess carbon content.
8. Q. What is Gasol?
Ans: The mixture of petrol with alcohol up to 20% is known gasol.
9.Q. Why Acetic acid is called glacier acid?
Ans: Acetic acid freezes at 290K in cold weather and form crystals.This is why acetic acid is called
glacier acid.

10. Q. What is saponification?


Ans: When sodium hydroxide react with ester and form alcohol and sodium Ethanoate. This reaction
is used to form soap So this reaction is known as saponification.
CH3COO C2H5

NaOH ------------> CH3COONa + C2H5OH

11. Q. Why does melting and boiling points of the member of Homologous Series increase
gradually ?
Ans: The number of carbon atoms in the molecule of the member of Homologous Series increases
gradually .Van der Waals dispersion forces will be very small for a molecule like methane but will
increase as the molecules get bigger. Therefore, the boiling points of the alkanes increase with
molecular size(increase in no. of c atom)
12. Q. Why does the viscosity of the member of Homologous Series increase gradually?
Ans: The viscosity increases as relative molecular mass and size increases.
13. Q. Why alkanes cannot dissolve in water but is soluble in organic solvent?
Ans: This is because alkane does not release a sufficient amount of energy to break the hydrogen
bonds in water. Therefore, the alkane does not dissolve.
14. Q. Why doesnt soap form micelles in ethanol as they form in water?
Ans: In organic solvent like ethanol, soap is completely soluble, hence no micelle is not formed
15. Q. What is observed on adding 5% solution of alkaline potassium permanganate solution
drop by drop to some warm ethanol taken in testube. Write the name of the compound formed
during chemical reaction.
Ans: When a 5% solution of alkaline potassium permanganate solution is added drop by drop to
some warm ethanol taken in a test tube, magenta colour of alkaline potassium permanganate
disappears and ethanol has been changed to carboxylic acid.
The reaction is as follows. CH3 - CH2OH

--------------- > CH3COOH

16. Q. How would you distinguish experimentally between an alcohol and a carboxylic acid on
the basis of a chemical property?
Ans: we take alcohol and a carboxylic acid in two separate test tubes. Add sodium hydrogen
carbonate in both the test tubes. The test tube, from which the effectiveness evolves, contains
carboxylic acid. The effervescence is due to the evolution of carbon dioxide gas. However, from test
tube containing alcohol there is to effervescence, because no carbon dioxide gas is produced there.
17. Q. A straight-chain alkane will have a boiling point higher than a branched-chain alkane?
Ans: This is due to the greater surface area in contact.
18. Q. Why do Alkanes stable and less reactive than alkenes ?
Ans: This is because saturated hydrocarbons contain only single bonds which are very stable and
difficult to break. On the other hand, unsaturated hydrocarbons contain pie bonds, which can be
easily broken as they are more strained.
19. Q. How can you check which one is saturated butter or vegetable oil?

Ans: Butter contain saturated compound where as cooking oil contain unsaturated compound. If
Alkaline KMno4 added to both, pink color of KMno4 disappear in cooking oil but remain in pink in
butter.
Vegetable Oil + H2
----Ni--------> CH3 - CH3
20. Q. What's the difference between cracking and pyrolysis?
Ans: Pyrolysis : The decomposition of a compound on heating in absence of air is known as
pyrolysis. Pyrolysis is used on a massive scale to turn coal into coke for metallurgy, and fractional
distillation
Cracking: The breakdown of large organic compounds by use of a catalyst and low temperature to
form fewer different compounds is called Cracking.
C22H46 ---> C11H24 (an alkane) + C11H22 (an alkene)
21. Q. What do you mean by Intra and Inter molecular dehydration of Ethanol?
Ans:
(a) Intra molecular dehydration:
Ethanol, when heated with excess conc. H2SO4 at 443 K undergoes intra molecular dehydration (i.e.
removal of water within a molecule of ethanol).
CH3CH2OH -------Conc.H2SO4/443K-----> CH2 = CH2 +H2O
(b) Inter molecular dehydration :
When excess of alcohol is heated with conc. H2SO4 at 413K two molecules condense by losing a
molecule of water to form ether (i.e. removal of water from two molecules of ethanol).
C2H5- OH + C2H5HO -------Conc.H2SO4/413K----> C2H5-O-C2H5 (Diethyl ether)+H2O
22. Q. Why is the conversion of ethanol to ethanoic acid an oxidation reaction?
Ans. When ethanol is oxidised, hydrogen is removed from its molecule and oxygen is added so as to
form ethanoic acid. Thus, conversion of ethanol into acetic acid is an oxidation reaction.
23. Q. A mixture of ethyne and oxygen is burnt for welding. Can you tell why a mixture of
ethyne and air is not used?
Ans: Ethyne is un saturated carbon compound and burns in air with a sooty flame, because the
oxygen from air is insufficient to burn the carbon completely. Thus, pure oxygen is used which
completely burns carbon and hydrogen and produces a very hot flame.
24. Q. How will you distinguish between alcohol and carboxylic acid experimentally? (V. Imp.)
Ans. Take two test tubes A and B and place about 1 g of sodium carbonate in them. Pour alcohol in
test tube A and carboxylic acid in test tube B. Shake the contents of the test tubes.
The test tube in which a brisk effervescence takes place, with the liberation of a colourless
gas (CO2) is carboxylic acid. The test tube in which no reaction takes place is alcohol.
25. Q. Unsaturated hydrocarbons show addition reactions but not saturated hydrocarbons?
Ans: In saturated hydrocarbons all the four bonds of carbon are fully utilised and no more hydrogen
or other atoms can attach to it. Thus, they can undergo only substitution reactions not addition
reactions.

26. Q. How can ethanol and ethanoic acid be differentiated on the basis of physical and
chemical properties?
Ans. Physical properties :
(a). Ethanol has a sharp bitter burning taste, whereas ethanoic acid has a sour taste.
(b) On cooling ethanol does not freeze, but ethanoic acid freezes.
Chemical Properties :
(a) Ethanol gets dehydrated by conc. sulphuric acid, but ethanoic acid does not get dehydrated by
conc. sulphuric acid.
(b) Ethanol does not displace hydrogen with zinc or magnesium, but ethanoic acid displaces
hydrogen with zinc or magnesium
27. Q. Saturated hydrocarbons burn with a blue flame while unsaturated hydrocarbons burn
with a sooty flame. Why?
Ans. This is because saturated hydrocarbon has high percentage of hydrogen than that of unsaturated
hydrocarbons
28. Q. Why is the reaction between methane and chlorine considered as a substitution
reaction.?
Ans: reaction between methane and chlorine is considered as a substitution reaction since the
hydrogen atoms of methane are replaced by chlorine atoms.
29. Q. How would you bring about the following conversions? Name the process and write the
reaction involved. (a) ethanol to ethene (b) propanol to propanoic acid.
Ans. (a) By the dehydration of ethanol in the presence of concentrated H2SO4
CH3 CH2 OH --------- Hot conc. H2SO4 CH2 = CH2 + H2O
(b) By the oxidation of propanol using oxidising agent such as alkaline KMnO4.
CH3 CH2 CH2 OH ---Alk. KMnO4 + Heat - CH3 CH2 COOH

31. Q. why sodium chloride added during preparation of soap?


Ans: This help to decrease solubility of soap and help in precipitation of soap from aqueous solution.
This preparation is known as salting out.
32. Q. Why is soap not used in acidic solution?
Ans: This is because free fatty acid of soap get precipitated
RCOO Na+
+
H+ ---------------> RCOOH

Na+

33. Q. Why are soap not effective as a cleaning agent in hard water?
Ans: Hard water contains sodium and magnesium ions. Soap form precipitate with these ions and
thus thrown out of the solution.
2RCOO Na+
+
Mg2+ ---------------> (RCOO)2 Mg
+
2Na+
34. Q. Alkanes (both alkanes and cycloalkanes) are virtually insoluble in water, but dissolve in
organic solvents. However, liquid alkanes are good solvents for many other non-ionic organic
compounds. Give reason.
Ans: Van der Waals forces do not release a sufficient amount of energy to compensate for the energy
required to break the hydrogen bonds in water. The alkane does not dissolve.
In most organic solvents, the primary forces of attraction between the solvent molecules are Van der
Waals - either dispersion forces or dipole-dipole attractions. Therefore, when an alkane dissolves in
an organic solvent, the Van der Waals forces are broken and are replaced by new Van der Waals
forces. The two processes more or less cancel each other out energetically; thus, there is no barrier to
solubility.
35. Q. What is the difference between Oxidation and combustion?
Answer: Combustion is the complete oxidation of organic compound into carbon dioxide and water
molecules in presence of oxygen gas while oxidation is the addition of oxygen in a organic
compound or with an element the loss of electron from an atom or ion is also oxidation.
Hence, all Oxidation reactions are not combustion reaction but all combustion reactions are
Oxidation. Oxidation reaction does not involve heat where as combustion reactions do.
36. Q.Why does Ethanoic acid called glacial acetic acid?
Ans. On cooling, pure Ethanoic acid is frozen to form ice like flakes. They look like glaciers, so it is
called glacial acetic acid.
37. Q. A mixture of ethyne and oxygen is burnt for welding. Can you tell why a mixture of
ethyne and air is not used?
Ans. Ethyne has only two hydrogen atoms and two carbon atoms in its molecule. It burns in air with
a sooty flame, because the oxygen from air is insufficient to burn the carbon completely. Thus, pure
oxygen is used which completely burns carbon and hydrogen and produces a very hot flame
38. Q. What is functional group ? need more to know
Ans: Functional group may be defined as an atom or group of atoms or reactive part which is
responsible for the characteristic properties of the compounds.
The chemical properties of organic compounds are determined by the functional groups while their
physical properties are determined by the remaining part of the molecule.
The general formula of alcohol is R-OH where R is an alkyl group and OH is the functional
group.

The general formula of aldehydes is R CHO where R is an alkyl group or hydrogen atom and
CHO is the functional group
The general formula of ketone is R-CO-R where R and R are alkyl groups and C=O is the
functional group
The general formula of acid is R-COOH where R is a hydrogen atom or alkyl group and COOH
is the functional group.
The general formula of esters is R-C=O- OR where R and R are alkyl groups and C=O OR is the functional group
39. Q. Why is graphite a good conductor of electricity?
Ans: Graphite is a good conductor of electricity. Its structure is the main reason for this property.
Each carbon atom in graphite is directly linked to only three carbon atoms through covalent bonds.
Therefore, out of the four valence electrons in a carbon atom, only three are used for bonding and the
fourth is relatively free and can move from one carbon atom to the other. These free electrons make
graphite a good conductor of electricity.
40. Q. (a) Differentiate between soap and detergent.
(b) Explain why, soaps form scum with hard water whereas detergents do not
Ans:
(a)Difference between soap and detergent:
Soap
(i) sodium salt of long chain carboxylic acid.
(ii) Soaps are biodegradable
(iii) Not suitable with hard water
Detergent
(i) Ammonium or sulphate of long chain of carboxylic acid.
(ii) Not biodegradable
(iii) Working well in hard water
(b) In hard water, due to the presence of Ca +2 and Mg +2 ions, soaps form insoluble salt. This
Precipitate is called scum.
Detergent does not show this property as its charged end does not react with Ca+2 and Mg+2
ions
41. Q. How does soap clean the clothes?
Ans: When dirty clothes are mixed with water and soap, the ionic part of the soap being water
attractive, dissolves in water whereas the hydrocarbon part of the soap being water repellent unites
with the oil or greese part. When dirty clothes are rinsed with water, the dirt particles attached with
the soap molecules, dissolve in water and come out. In this way, clothes become clean.

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