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L-4 CARBON AND ITS COMPOUNDS Notes

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23 views104 pages

L-4 CARBON AND ITS COMPOUNDS Notes

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nishitagupta790
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CHAPTER - 4

CARBON AND ITS COMPOUNDS


Occurrence of carbon :-
i) Carbon is found in the atmosphere, inside the earth’s crust and in
all living organisms.
ii) Carbon is present in fuels like wood, coal, charcoal, coke, petroleum,
natural gas, biogas, marsh gas etc.
iii) Carbon is present in compounds like carbonates,
hydrogen carbonates etc.
iv) Carbon is found in the free state as diamond, graphite, fullerenes etc.
SOME INTERESTING FACTS ABOUT CARBON
❖ Carbon is an element, belong to non-metal and its symboI is ”C”
❖ The name of the ‘Carbon’ derived from the Latin word “Carbo’ which
means coal. This is because carbon is the main constituent of coal.
❖ It is the fourth most abundant element in the universe
❖ H He O C
❖ PPM 739000 240000 10400 4600
❖ It is the 15th most abundant element in earth’s crust
❖ O > Si > Al > Fe> Ca > Na > K > Mg > Ti > H
❖ It is 2nd abundant element in the human body
❖ O C H N Ca P K
❖ 65% 18% 10% 3% 1.5% 1.2% 0.2%
❖ Carbon is found in the atmosphere (0.03%) as Carbon dioxide.
❖ Inside the earth’s crust (0.02%) as Minerals (like carbonates, coal &
petroleum)
❖ In all living organisms as organic compounds
❖ Carbon is found in the free state as diamond, graphite & fullerenes.
Importance of carbon compounds
🔾 Foods - starch, sugar, fats, vitamins, proteins
🔾 Fuels - wood, coal, alcohol, petrol
🔾 Poisons - opium, strychnine
🔾 Drugs and disinfectants - penicillin, quinine, aspirin, sulpha drugs
🔾 Household and commercial articles -paper, soap, cosmetics, oils, paints
🔾 Textile fabrics - cotton, wool, silk, linen, rayon, nylon
🔾 Perfumes - vanillin, camphor
🔾 Dyes - indigo, congo red, malachite green
🔾 War gases - mustard gas, chloropicrin, lewisite
🔾 Explosives - nitroglycerine, dynamite, picric acid, TNT
Bonding in carbon – Covalent bond :-
The atomic number of carbon is 6, its electronic arrangement is 2,4, it
has 4 valence electrons. It can attain stability by gaining 4 electrons,
losing 4 electrons or sharing 4 electrons with other atoms.
It does not gain 4 electrons because it is difficult for the 6 protons to
hold 10 electrons.
It does not lose 4 electrons because it needs a large amount of
energy to lose 4 electrons.
So it shares 4 electrons with other atoms to attain stability resulting in
the formation of covalent bonds.
Since carbon atom needs 4 electrons to attain stability, its valency is 4
and it is tetravalent.

X
I
_ _
X
C X
C
X I
Formation of covalent bonds :-
Covalent bond is chemical bond formed by the sharing of electrons
between atoms.
The sharing of one pair of electrons results in the formation of single
covalent bond, sharing of two pairs of electrons results in the formation
of double covalent bond and sharing of three pairs of electrons results
in the formation of triple covalent bond.
Eg :- Formation of single covalent bond in Hydrogen
molecule - H2
The atomic number of hydrogen is 1, its electronic arrangement is 1, it
has 1 valence electron. It needs 1 electron more to attain stability. So
two hydrogen atoms share 1 pair of electrons resulting in the formation
of a single covalent bond in hydrogen molecule H 2.

Hx + x H H XX H H–H H2
Electron dot structures :-
Methane molecule – CH4 Ethane molecule – C2H6

H H H

X X X

X
H X C X H H X C X
C X H
X X X

H H H

H H H
I I I
H–C–H H –C –C –H
I I I
ALLOTROPES OF CARBON

● “The various physical forms in which an element can


exist are called allotropes of the elements”.

● The carbon element exist in three solid forms called allotropes. They are

1) Diamond 2) Graphite 3) Buckminsterfullerene

● Diamond & graphite are two common allotropes of carbon which are known
to us for centuries, Buckminsterfullerene is the new allotrope of carbon
which has been discovered recently

● The properties of diamond & graphite are well known but the properties of
Buckminsterfullerene are still being investigated.

● All the allotropes of carbon burns on strong heating to form carbon dioxide,
and the formed carbon dioxide gas if it pass through lime water. It turns to
milky, It shows that all the allotropes of carbon contain carbon.
DIAMOND
● Diamond is a colorless transparent substance

having extraordinary brilliance.

● Diamond is quite heavy and extremely hard

● It is the hardest natural substance known in the

nature

● Diamond does not conduct electricity


STRUCTURE OF DIAMOND

● Each carbon atom in the diamond


crystal is linked to four other carbon
atoms by strong covalent bonds, the
four surrounding Carbon atoms are at
the four corners of a regular
tetrahedron and which are powerfully
bonded to one another forms a
network of covalent bonds, due to this
diamond structure is very rigid. This
rigid structure make it very hard, and
also responsible for High density and
melting point.
● Diamond is a non conductor of electricity
● Carbon atom has 4 valence electron in it. In a diamond crystal, each
carbon atom is linked to 4 other carbon atoms by covalent bonds,
and hence all the 4 valence electrons of each carbon atom are used
up in forming the bonds. Since there are “ no free electrons” in a
diamond crystal, it does not conduct electricity.
● Diamonds can be made artificially by subjecting pure carbon to very
high pressure & temperature. These are called synthetic diamonds.
● synthetic diamonds are small but are otherwise indistinguishable from
natural diamonds.
USES OF DIAMONDS:
● In glass cutter
● For making Jewellery
● A sharp, diamond edged knife (called keratoma) is used by
eye surgeons to remove cataract from eye.
● As diamond studded saws & drill bits.
GRAPHITE

The structure of graphite is very


different from that of diamond. A
graphite crystal consists of layers of
Carbon atoms.
GRAPHITE STRUCTURE
● Each carbon atoms in a graphite layer is joined to three other carbon atoms by
strong covalent bonds to form flat hexagonal rings structure called ”Array”. The
various layers of carbon atoms in graphite are quite far apart so that no covalent
bonds can exist between them. The various layers of carbon atoms in graphite are
held together by weak van der waals forces. Since the various layers of carbon
atoms in graphite are joined by weak forces. They can slide over one another.
● Due to the sheet like structure graphite is a comparatively soft substance. It is the
softness of graphite which makes it useful as a dry lubricant for machine parts.
● Graphite is a good conductor of electricity it is because in a graphite crystal. Each
carbon atoms is joined to only three other carbon atoms by covalent bonds, Thus
only the three valence electrons of each carbon atoms in graphite are used in bond
formation. The fourth valence electron of each carbon atom is “free” to move
● Due to the “presence of free electrons” in a graphite crystal, it conducts electricity.
● Like diamond, graphite also has very high melting point.
USES OF GRAPHITE

● Due to its softness used as lubricants both dry and wet forms

● Graphite is good conductor of electricity due to which graphite


is used for making carbon or graphite electrode in dry cells &
electric arcs.

● Graphite is used in making pencil leads.


BUCK MINSTER FULLERENE
Buckminsterfullerene is an allotrope
of carbon containing clusters of 60
carbon atoms joined together to form
spherical molecules
● It is a dark solid at room temperature
● It differs from the other two allotropes of carbon, diamond
& graphite are giant molecules which consists of an
unending network of carbon atoms but
buckminsterfullerene is very small molecule made up of
only 60 carbon atoms.
● Diamond is extremely hard whereas graphite is soft. On
the other hand, buckminsterfullerene is neither very hard
nor soft.
● Other properties of buckminsterfullerene are still being
investigated.
Versatile Nature of Carbon:-
Carbon forms a very large number of compounds. The number of
carbon compounds is more than three million. It is more than the
number of compounds formed by all other elements. This is because :-
i) Carbon atom can form bonds with other carbon atoms to form long
chains, branched chains and closed rings. This property is called
catenation.
ii) Since the valency of carbon is 4, it can form bonds with other
carbon atoms or with atoms of other elements like hydrogen,
oxygen, nitrogen, halogens etc.
I
_
C_
I I I I I I I I I I C
_ C–C–C–C–C–C _ _ _
C–C–C–C C C
I I I I I I I I I I C C
_C _ C
I
Long chain Branched chain Closed ring
Why study of Carbon Compounds is
a separate branch of Chemistry?
🔾It is due to the vastness in the number of
Carbon Compounds

Carbon with other elements such as H,N,O,F Cl,Br,I,S…


forms more than 5 million compounds

The other elements altogether forms about 70,000


compounds only
Reasons for Versatile Nature of
Carbon

1.Catenation
2.Tendency to form multiple
bonds
3.Tetra-covalency
4.Stable Carbon Compounds
5.Isomerism
Catenation
● Carbon atom can form bonds with other carbon
atoms to form a long chains, branched chain and
closed rings. This property is called Catenation.

NORMAL BUTANE (C4H10) ISO BUTANE (C4H10)

Long chain Branched chain

CYCLOHEXANE (C6H12)
Closed ring
Carbon atom can form multiple
covalent bonds
● If sufficient number of other atoms are
not there…
● In order to satisfy the four valences carbon
form double or triple bond between two C
atoms

ETHANE ETHENE ETHYNE


Tetra-covalency
● Since valency of carbon is 4, it can form bonds with other
carbon atoms or with atoms of other elements like
Hydrogen, Oxygen, Nitrogen and Halogens etc.,

Chloromethane Di Chloromethane Tri Chloromethane Tetra Chloromethane


CH3Cl CH2Cl2 CHCl3 CCl4

Carbon Disulphide Carbon Dioxide Urea


CS2 CO2
CO(NH2)2
Stable carbon compounds

-Small size of Carbon


-Nuclear capacity to hold shared electrons
strongly
Classification of Hydrocarbons
HYDROCARBON

OPEN CHAIN - CLOSED CHAIN


ALLIPHATIC

ALICYCLIC AROMATIC

SATURATED UN SATURATED

ALKANES-SINGLE ALKENES-DOUBLE ALKYNES-TRIPLE


BONDED BONDED BONDED
Hydrocarbons
● Organic compounds containing carbon and
hydrogen only
6) Hydrocarbons, Saturated and Unsaturated hydrocarbons :-
i) Hydrocarbons :- are compounds containing carbon and hydrogen
atoms.

ii) Saturated hydrocarbons :- are hydrocarbons having all single


covalent bonds between the carbon atoms.
Eg : Alkanes :- have all single covalent bonds between the carbon
atoms and their names end with – ane.

H
I
Methane – CH4 H–C–H
I
H

H H
I I
Ethane – C2H6 H–C–C–H
I I
H H
iii) Unsaturated hydrocarbons :- are hydrocarbonsving a double or
triple covalent bond between two carbon atoms. Eg : Alkenes and
Alkynes.
Alkenes :- have a double covalent bond between two carbon atoms.
and their names end with – ene.
H H H H
I I I I
Ethene - C2H4 C=C Propene – C3H6 H – C = C – C – H
I I I I
H H H H
Alkynes :- have a triple covalent bond between two carbon atoms
and their names end with – yne.

Ethyne – Ethyne – C2H2 H–CΞC–H

H
I
Propyne - C3H4 H–C ΞC–C–H
I
H
Alkenes :-
Alkenes have general molecular formula CnH2n . Their names end
with – ene and the members are as follows :-
Ethene - C2H4
Propene - C3H6
Butene - C4H8
Pentene - C5H10

H H
I I
Ethene :- C2H4 C=C
I I
H H

H H H H H H H
I I I I I I I
Propene :- C3H6 H–C=C–C–H Butene :- C4H8 H–C=C–C–C–H
I I I
H H H
Alkynes :-
Alkynes have general molecular formula CnH 2n – 2 .Their names end
with – yne and the members are as follows :-
Ethyne - C 2H 2
Propyne - C3H4
Butyne - C 4H 6

Ethyne :- C2H2 H–C


C–H
H
I
Propyne :- C3H4 H – C C–C–H
I
H
H H
I I
Butyne :- C4H6 H – C C–C–C–H
I I
Steps to draw structures of Saturated Carbon
Compounds- E.g.- Ethane {C₂H6}
1. Link the to carbon atoms together by a single bond.
C-C

1. Attach Hydrogens as per need to satisfy tetravalency of C and given in molecular


formula.- That is structural formula of given compound.

1. You can write condensed structural formula.

1. Represent dot structure


Prefixes of Alkanes, Alkenes
and Alkynes
Carbon Compounds
Isomerism :-
Carbon compounds having the same molecular formula but different
structural formulae are called isomers. This property is called isomerism.
Eg:- Butane – C4H10 has 2 isomers. They are Normal butane and Iso butane.
H H H H H H H
I I I I I I I
H–C–C–C–C–H H–C–C–C–H Iso butane
I I I I I I
H H H H H H
H– C –H
Normal butane I
H
Pentane – C5H12 has 3 isomers. They are Normal pentane, Iso pentane and Neo
pentane. Neo pentane
Iso pentane H
H I
I H– C–H
Normal pentane H–C–H H H
I I
H H H H H H H H H –C– C– C–H
I I I I I I I I I I
H–C–C–C–C–C–H H–C–C–C–C–H H H
I I I I I I I I I H–C–H
H H H H H H H H H I
H
Isomerism
● Compounds having same molecular formula but different
structures are known as Isomers and this phenomenon
is called Isomerism
Ex : Butene – C4H10 has 2 isomers. They are Normal Butane and
isobutane.

Normal butane C4H10 Isobutane C4H10


Ex : Pentane – C5H12 has 3 isomers. They are normal pentane, isopentane
and neopentane.

Normal pentane C5H12 Isopentane C5H12

Neopentane C5H12
Isomers of Hexane [C6H14]
Number of Isomers for alkanes:
8) Functional groups :-
An atom or a group of atoms which decides the properties of a
carbon compound is called a functional group.
i) Halide ( Halo group) :- - Cl, - Br, etc. ( Names end with – ane )
Eg :- CH3Cl – Chloro methane, C2H5Br – Bromo ethane

ii) Alcohol :- - OH ( Names end with – ol )


Eg :- CH3OH – Methanol, C2H5OH – Ethanol

H
iii) Aldehyde :- - CHO -C ( Names end with – al )
O
Eg :- HCHO – Methanal, CH3CHO – Ethanal
O
II
iv) Carboxylic acid :- - COOH - C - OH (Names end with – oic acid )
Eg :- HCOOH – Methanoic acid, CH3COOH – Ethanoic acid
v) Ketone :- - CO - C - (Names end with – one )
II
O
Eg :- CH3COCH3 – Propanone , CH3COC2H5 - Butanone
Homologous Series
● Homologous series is a group of carbon compounds
having similar structure, similar chemical
properties and whose successive members is differ
by a –CH2 group
Homologous Series of
Alkanes Alkenes Alkynes
CH4 C2H4 C2H2
C2H6 C3H6 C3H4
C3H8 C4H8 C4H6
C4H10 C5H10 C5H8
Characteristics of homologous series :
(i) All members of a homologous series can be represented by the
same general formula. For example, the general formula of the
homologous series of alkanes is CnH2n+2, in which ‘n’ denotes
number of carbon and hydrogen atoms in one molecule of alkane.
(ii) Any two adjacent homologues differ by one carbon atom and
two hydrogen atoms in their molecular formulae.
(iii) The difference in the molecular masses of any two adjacent
homologues is 14u.
(iv) All the compounds of a homologous series show similar
chemical properties.
(v) The members of a homologous series show a gradual change in
their physical properties with increase in molecular mass.
Question 2. Is there any similarity in these three?

● Answer:All these three have alcoholic (-OH)


functional group.

Question 3. Arrange these alcohols in the order of


increasing carbon atoms to get a family. Can we
call this family a homologous series?

● Answer: CH3OH, C2H5OH, C3H7OH, C4H9OH.


Yes, It is a homologous series of alkane alcohols as
each successive member of the series differs by -
CH2 unit from proceeding member
Question 1
How many structural isomers can you draw for pentane ?
Answer:
Three, these are n-pentane, iso-pentane and neo-pentane.
Question 2
What are the two properties of carbon which lead to
the huge number of carbon compounds we see around
us ?
Answer:
(i) Tetravalency
(ii) Catenation.
What will be the formula and electron dot structure
of cyclopentane ?
Answer:
The molecular formula of cyclopentane is C5 H10 .
Explain the nature of the covalent bond using the
bond formation in CH3Cl.

Covalent bond is formed by


sharing of electrons so that
the combining atoms complete their outermost shell.

In CH3Cl : C = 6, H = 1 and Cl = 17 And their electronic


configuration is C – 2,4, H – 1 and Cl – 2, 8, 7
Nomenclature of open chain
Hydrocarbons
● According to International Union of Pure and
Applied Chemistry(IUPAC)
● The name consists of two parts
1) Indicating number of Carbon atoms-
’Alk’part

2)Indicating the type of bonding-’Primary


suffix’
‘Alk ‘ part
No. of C atoms ‘Alk’ part
1 Meth
2 eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
8 Oct
9 Non
10 Dec
Primary Suffix

● If all the bonds are single bond


‘ane’

● If one double bond


‘ene’

● If one triple bond ‘yne’


Thus
⮚Single bonded compounds have the
name- Alk+ane =Alkane
⮚Double bonded compounds have the
name- Alk+ene =Alkene
⮚Triple bonded compounds have the name-
Alk+yne =Alkyne
Example No of carbon atom=4
alk part is but

All the C-C bonds are single bond


primary suffix is ane

Therefore the name is butane


Chemical properties of Carbon compounds :-
a) Combustion :-
Carbon compounds burn in oxygen to form water, carbon dioxide,
heat and light.
Eg :- C + O2 CO2 + heat + light
CH4 + 2O2 2H2O + CO2 + heat + light
C2H5OH + 3O2 3H2O + 2CO2 heat + light

b) Oxidation :-
Carbon compounds like alcohols are oxidised to carboxylic acids on
heating with oxidising agents like alkaline Potassium permanganate
– KMnO4 or acidic potassium dichromate - K2Cr2O7 .
Eg:- Alcohols are oxidised to Carboxylic acids
alkaline KMnO4 + heat
C2H5OH CH 3COOH
Ethanol acidic K2Cr2O7 + heat Ethanoic acid
c) Addition reaction :-
Unsaturated hydrocarbons undergo addition reaction with hydrogen in the
presence of nickel or palladium as catalyst to form saturated hydrocarbons.
Eg:- Ethene undergoes addition reaction with hydrogen to form ethane in the
presence of nickel or palladium as catalyst.
Ni or Pd catalyst
C2H4 + H2 C2H6
H H H H
I I Ni or Pd catalyst I I
C = C + H2 H–C–C–H
I I I I
H H H H
The addition of hydrogen to unsaturated hydrocarbons to form saturated
hydrocarbons is called hydrogenation. Hydrogenation is used to convert
unsaturated oils and fats to saturated oils and fats.
d) Substitution reaction :-
Saturated hydrocarbons undergo substitution reaction with halogens to
form substitution products.
Eg :- Methane undergoes substitution reaction with chlorine in the presence
of sunlight to form substitution products.
CH4 + Cl2 CH3Cl + HCl CH3Cl + Cl2 CH2Cl2 + HCl
CH2Cl2 + Cl2 CHCI3 + HCl CHCI3 + Cl2 CCl4 + HCl
Chemical Properties of Carbon
Compounds
● Combustion-Burning in oxygen
● Gives oxides
● Exothermic-produces heat and also light
● Saturated compounds give a clean flame
while unsaturated compounds give sooty
flame
Oxidation
● Oxidation –Addition of oxygen
Example
Addition Reactions
● A molecule add to another molecule by
breaking of bonds
● Unsaturated hydrocarbon add hydrogen in
presence of catalyst such as Palladium or
Nickel

● This reaction is used in the hydrogenation of


vegetable oils
Substitution reactions
● An atom or a group replaces another atom
or group in a compound
Some important carbon compounds :-
a) ETHANOL :- C2H5OH - Ethyl alcohol
Properties :-
i) Ethanol is a colourless liquid with a pleasant smell and burning
taste.
ii) It is soluble in water.
iii) Ethanol reacts with sodium to form sodium ethoxide and hydrogen.
2C2H5OH + 2Na 2C2H5ONa + H2
iv) Ethanol reacts with hot conc. H 2SO4 to form ethene and water. Conc.
H2SO4 is a dehydrating agent and removes water from ethanol.
conc. H2SO4
C2H5OH C 2H4 + H2O
Uses :-
i) Ethanol is used for making alcoholic drinks.
ii) It is used as a solvent.
iii) It is used for making medicines like tincture iodine, cough syrups,
tonics etc.
ETHANOL-CH3CH2OH
● Ethanol is a liquid at room temperature
● It is the active ingredient of all alcoholic
drinks
● It is a good solvent-therefore it is used in
medicines such as Tincture of Iodine ,
Cough syrups , Tonic…
Reactions
● With sodium-

● Reaction to give unsaturated


Hydrocarbon-with conc H2SO4 at 443K
● Involve removal of water and is called
Dehydration
b) ETHANOIC ACID :- CH3COOH – Acetic acid

Properties :-
i)Ethanoic acid is a colourless liquid with a pungent smell and sour taste.
ii) It is soluble in water.
iii) A solution of 5% to 8% ethanoic acid in water is called Vinegar.
iv) Esterification :-
Ethanoic acid reacts with ethanol to form the ester ethyl ethanoate in the presence
of conc. H2SO4.
conc.H2SO4
CH3COOH + C2H5OH CH3COOC2H5 + H2O
The reaction between carboxylic acid and alcohol to form an ester is called
esterification.
v) Saponification :-
When an ester reacts with sodium hydroxide solution, the sodium salt of the
carboxylic acid and the parent alcohol are formed. This reaction is called
saponification.
Eg :-Ethyl ethanoate reacts with sodium hydroxide to form sodium acetate and ethanol.
CH3COOC2H5 + NaOH CH3COONa + C2H5OH
vi) Ethanoic acid reacts with bases to form salt and water.
CH3COOH + NaOH CH3COONa + H2O
vii) Ethanoic acid reacts with carbonates and hydrogen carbonates to form salt, water
and carbon dioxide.
2CH3COOH + Na2CO3 2CH3COONa + H2O + CO2
CH3COOH + NaHCO3 CH3COONa + H2O + CO2
Ethanoic acid -CH3COOH
● Commonly known as Acetic acid
● 5-10%solution of acetic acid is called
Vinegar
● Vinegar is a preservative for pickles
● Its melting point is 290K
● It freezes in cold climate-therefore known as
Glacial acetic acid
● It is a weak acid
Reactions
● Esterification –Reaction with Alcohols
● Esters which are fruit smelling substances are
formed
Reaction with a base
Reaction with Carbonates and
Bicarbonates
Soaps and detergents :-
a) Soaps :- Soaps are long chain sodium or potassium salts of carboxylic
acids. Eg:- Sodium stearate – C17H35COONa
Structure of soap molecule :- A soap molecule has two parts. A long
hydrocarbon part which is hydrophobic (water repelling) and soluble in oil and
grease and a short ionic part which is hydrophyllic (water attracting) and
insoluble in oil and grease.

COO-- Na
+

Hydrocarbon part Ionic part


(Water repelling) (Water attracting)
Cleansing action of soap :- When soap is dissolved in water it forms
spherical structures called micelles. In each micelle the soap molecules are
arranged radially such that the HC part is towards the centre and the ionic part
is towards the outside. The HC part dissolves the dirt, oil and grease and forms
an emulsion at the centre of the micelles which can be washed away by water.
Arrangement of stearate ion at low concn Arrangement of stearate ion above CMC
Cleansing Action of Soap
● Oil and grease are absorbed into the
hydrophobic centers of soap micelles and
are washed away.
b) Detergents :-
Detergents are long chain sodium salts of sulphonic acids.
Soaps do not wash well with hard water because it forms insoluble
precipitates of calcium and magnesium salts in hard water.
Detergents wash well with hard water because it does not form insoluble
precipitates of calcium and magnesium salts in hard water.

c) Differences between soaps and detergents :-

Soaps Detergents

i) Soaps are sodium salts of Detergents are sodium salts of


fatty acids. sulphonic acids.
ii) Soaps clean well in soft water but Detergents clean well with both
do not clean well in hard water. hard and soft water.
iii) Soaps do not clean as well as Detergents clean better than soaps.
detergents.
iv) Soaps are biodegradable and Some detergents are non biodegradable
do not cause pollution. and cause pollution.
Thank
You

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