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CHAPTER 8 INTRODUCTION TO ORGANIC CHEMISTRY

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Title: CHAPTER 8 INTRODUCTION TO ORGANIC CHEMISTRY


1
CHAPTER 8INTRODUCTION TO ORGANIC CHEMISTRY
  • BASIC CHEMISTRY
  • CHM 138

2
ORGANIC CHEMISTRY
  • Organic chemistry
  • The branch of chemistry that deals with carbons
    compounds.
  • Organic derived from living organisms
  • Study of compounds extracted from living
    organisms and their natural products.
  • Examples sugar, starch, urea, waxes,
    carbohydrates, fats and etc
  • Human are composed of organic molecules
    proteins in skin, lipid in cell membranes,
    glycogen in livers and the DNA in the nuclei of
    cells.

3
  • Chemistry of carbon
  • - Two stable isotops (13C and 12C)
  • - electron configuration 1s2 2s2 2p2
  • - four valence electrons
  • - can form more compounds than any other
    element
  • - able to form single, double and triple
    carbon-carbon bonds, and to link up with each
    other in chains and ring structures

4
HOMOLOGUE SERIES AND FUNCTIONAL GROUPS
  • Functional group
  • A group of atoms that is largely responsible for
    the chemical behavior of the parent molecule.
  • Functional groups
  • - hydrocarbons
  • - alcohols
  • - aldehydes
  • - ketones
  • - carboxylic acids
  • - alkyl halides

5
HYDROCARBONS
  • Made up of only hydrogen and carbon

6
ALKANES
  • General formula
  • CnH2n2, where n 1, 2, .
  • Only single covalent bonds are present
  • Known as saturated hydrocarbons because contain
    the maximum number of hydrogen atoms that can
    bond with the number of carbon atoms present.
  • Can be assumed to be sp3-hydridized

7
Structures of the first four alkanes
8
The melting and boiling points of the
straight-chain isomers of the first 10 alkanes
9
Homologous Series 
  1. Definition A series of compounds in which each
    member differs from the next by a specific number
    and kind of atoms.
  2. Alkanes Differ only at number of (CH2)
  3. Series of compounds that has the same functional
    group.

10
INITIAL NAMES OF THE HOMOLOGOUS SERIES
Number of carbon atoms, n Name
1 Meth
2 Eth
3 Prop
4 But
5 Pent
6 Hex
7 Hept
8 Oct
9 Non
10 Dec
11
NAMING ALKANES
  • Alkyl groups are used to name organic compounds.
  • The general formula of an alkyl group is CnH2n1.
  • The letter R is often used in formulas to
    represent any of the possible alkyl groups.
  • R CnH2n1 (any alkyl group)
  • R CH3 methyl group
  • R CH3CH2 ethyl group

12
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13
IUPAC RULES International Union of Pure and
Applied Chemistry
RULE 1. Select the longest continuous chain of
carbon atoms as the parent compound.
  • Consider all alkyl groups attached to it as
    branch chains or substituents that have replaced
    hydrogen atoms of the parent hydrocarbon. If two
    chains of equal length are found, use the chain
    that has the larger number of substituents
    attached to it.
  • The alkanes name consists of the parent
    compounds name prefixed by the names of the
    alkyl groups attached to it.

14
This structure has 2 chains.
15
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16
This is a methyl group.
It is a branch chain and can be considered to
have replaced a hydrogen on the parent compound.
17
1
2
4
5
6
3
18
IUPAC RULES
RULE 2. Number the carbon atoms in the parent
carbon chain starting from the end closest to the
first carbon atom that has an alkyl group
substituted for a hydrogen atom.
  • If the first subsitutent from each end is on the
    same-numbered carbon, go to the next substituent
    to determine which end of the the chain to start
    numbering.

19
If the chain is numbered left to right, the
isopropyl group is on carbon 5.
isopropyl group
20
If the chain is numbered right to left, the
isopropyl group is on carbon 4.
Use right to left numbering so that the isopropyl
group is on the lowest numbered carbon.
4-isopropyloctane
isopropyl group
21
IUPAC RULES
  • RULE 3. Name each alkyl group and designate its
    position on the parent carbon chain by a number
    (e.g., 2-methyl means group attached to C-2).

22
RULE 4. When the same alkyl-group branch chain
appears more than once, indicate this repetition
by a prefix (di-, tri-, tetra- and so forth)
written in front of the alkyl group name (e.g.
dimethyl indicates two methyl groups). The
numbers indicating the alkyl-group positions are
separated by a command and followed by a hyphen
and are placed in front of thename (e.g.,
2,3-dimethyl).
23
  • RULE 5. When several different alkyl groups are
    attached to the parent compound, list them in
    alphabetical order (e.g. ethyl before methyl in
    3-ethyl-4-methyloctane). Prefixes are not
    included in alphabetical ordering (ethyl comes
    before dimethyl).

24
1
2
4
5
3
6
7
8
3
4
25
  • Alkanes can have many different types of
    substituents.
  • For example

26
CYCLIC HYDROCARBONS
  • A hydrocarbon that contains carbon atoms joined
    to form a ring.
  • Cycloalkanes all carbons of the ring are
    saturated

27
NOMENCLATURE OF CYCLOALKANES
  • Similar to that alkanes. For examples

28
ISOMERISATION
  • Structural isomers
  • Molecules that have the same molecular formula,
    but different structure

Three isomers of pentane (C5H12)
29
STRUCTURE ISOMERS FOR ALKANES
NAME MOLECULAR FORMULA TOTAL OF ISOMERS
Methane CH4 1
Ethane C2H6 1
Propane C3H8 1
Butane C4H10 2
Pentane C5H12 3
Hexane C6H14 5
Heptane C7H16 9
Octane C8H18 18
Nonane C9H20 35
Decane C10H22 75
30
ALKENES
  • Also called olefins
  • Contain at least one carbon-carbon double bond
    (CC)
  • General formula, CnH2n (n2,3,)
  • Classified as unsaturated hydrocarbons (compound
    with double or triple carbon-carbon bonds that
    enable them to add hydrogen atoms.
  • sp2-hybridized
  • For example
  • C2H4 - ethylene

31
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32
ALKYNES
  • Alkynes contain at least carbon-carbon triple
    bond.
  • General formula CnH2n-2, where n 2, 3,.
  • Alkyne nomenclature
  • Used suffix yne
  • Same as alkene nomenclature

33
NamingAlkenes and Alkynes
34
IUPAC RULES
  • RULE 1. Select the longest continuous carbon
    chain that contains a double or triple bond.

35
  • RULE 2. Name this compound as you would an
    alkane, but change ane to ene for an alkene and
    to yne for an alkyne.

This is the longest continuous chain. Select it
as the parent compound.
36
  • RULE 2. Name this compound as you would an
    alkane, but change ane to ene for an alkene and
    to yne for an alkyne.

This chain contains a triple bond. Name the
parent compound octyne.
37
RULE 3. Number the carbon chain of the parent
compound starting with the end nearer to the
double or triple bond. Use the smaller of the
two numbers on the double- or triple-bonded
carbon to indicate the position of the double or
triple bond. Place this number in front of the
alkene or alkyne name.
38
IUPAC RULES
This end of the chain is closest to the double
bond. Begin numbering here.
39
IUPAC RULES
The name of the parent compound is 1-octene.
4
3
2
1
5
6
7
8
40
IUPAC RULES
The name of the parent compound is 1-octyne.
41
RULE 4. Branched chains and other groups are
treated as in naming alkanes. Name the
substituent group, and designate its position on
the parent chain with a number.
42
IUPAC RULES
43
IUPAC RULES
44
  • must specify whether the molecule is cis or
    trans (geometric isomer)
  • cis two particular atoms (or groups of atoms)
    are adjacent to each other
  • trans the two atoms (or groups of atoms) are
    across from each other

45
CYCLOALKENES
  • Contains CC in the ring
  • Nomenclature of cycloalkenes
  • Similar to that alkenes
  • Carbons atoms in the double bond are designated
    C1 and C2

46
AROMATIC HYDROCARBONS
  • Contain one or more benzene rings

Benzene Kekulé Structure
6 carbons in a ring
3 double bonds
47
The structure of benzene can be represented in
two abbreviated ways.
The corner of each hexagon represents a carbon
and a hydrogen atom.
48
Naming Aromatic Compounds
49
  • A substituted benzene is derived by replacing one
    or more of benzenes hydrogen atoms with an atom
    or group of atoms.
  • A monosubstituted benzene has the formula C6H5G
    where G is the group that replaces a hydrogen
    atom.
  • All hydrogens in benzene are equivalent.
  • It does not matter which hydrogen is replaced by
    G.

50
Monosubstituted Benzenes
51
Some monosubstituted benzenes are named by adding
the name of the substituent group as a prefix to
the word benzene.
  • The name is written as one word.

nitrobenzene
ethylbenzene
52
  • Certain monosubstituted benzenes have special
    names.
  • These are parent names for further substituted
    compounds.

phenol
toluene
53
benzoic acid
aniline
54
  • C6H5 is the phenyl group.
  • It is used to name compounds that cannot be
    easily named as benzene derivatives.

diphenylmethane
4-phenyl-2-pentene
55
Disubstituted Benzenes
56
  • Three isomers are possible when two substituents
    replace hydrogen in a benzene molecule.
  • The prefixes ortho-, meta- and para- (o-, m- and
    p-) are used to name these disubstituted benzenes.

57
ortho-dichlorobenzene(1,2-dichlorobenzene)mp
17.2oC, bp 180.4oC
58
meta-dichlorobenzene(1,3-dichlorobenzene)mp
24.82oC, bp 172oC
59
para-dichlorobenzene(1,4-dichlorobenzene)mp
53.1, bp 174.4oC
60
When one substituent corresponds to a
monosubstituted benzene with a special name, the
monosubstituted compound becomes the parent name
for the disubstituted compound.
m-nitrophenol
phenol
61
When one substituent corresponds to a
monosubstituted benzene with a special name, the
monosubstituted compound becomes the parent name
for the disubstituted compound.
m-nitrotoluene
toluene
62
Tri- and Polysubstituted Benzenes
63
  • When a benzene ring has three or more
    substituents, the carbon atoms in the ring are
    numbered.
  • Numbering starts at one of the substituent
    groups.
  • The numbering direction can be clockwise or
    counterclockwise.
  • Numbering must be in the direction that gives the
    substituent groups the lowest numbers.

64
clockwise numbering
6
1
5
4
2
3
1,4,6-trichlorobenzene
65
counterclockwise numbering
chlorine substituents have lower numbers
2
1
3
4
6
5
1,2,4-trichlorobenzene
66
  • When a compound is named as a derivative of the
    special parent compound, the substituent of the
    parent compound is considered to be C-1 of the
    ring.

67
1
6
2
3
5
2,4,6-trinitrotoluene(TNT)
4
toluene
68
ALCOHOLS
  • Alcohols Organic compounds containing hydroxyl
    (-OH) functional groups.
  • Phenols Compounds with hydroxyl group bonded
    directly to an aromatic (benzene) ring.

69
CLASSIFICATION
  • According to the type of carbinol carbon atom (C
    bonded to the OH group).
  • Classes
  • i) Primary alcohol
  • - -OH group attached to a primary carbon
    atom
  • ii) Secondary alcohol
  • - -OH group attached to a secondary
    carbon atom
  • iii) Tertiary alcohol
  • - -OH group attached to a tertiary
    carbon atom

70
  • TYPE STRUCTURE
    EXAMPLES
  • Primary (1)
  • Secondary (2)
  • Tertiary (3)

71
Polyhydroxy Alcohols
  • Alcohols that contain more than one OH group
    attached to different carbons are called
    polyhydroxy alcohols.
  • Monohydroxy one OH group per molecule.
  • Dihydroxy two OH groups per molecule.
  • Trihydroxy three OH groups per molecule.

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73
Naming Alcohols
74
IUPAC RULES
  1. Select the longest continuous chain of carbon
    atoms containing the hydroxyl group.
  2. Number the carbon atoms in this chain so that the
    one bonded to the OH group has the lowest
    possible number.
  3. Form the parent alcohol name by replacing the
    final e of the corresponding alkane name by ol.
    When isomers are possible, locate the position
    of the OH by placing the number (hyphenated) of
    the carbon atom to which the OH is bonded
    immediately before the parent alcohol name.
  4. Name each alkyl branch chain (or other group) and
    designate its position by number.

75
This is the longest continuous chain that
contains an hydroxy group.
Select this chain as the parent compound.
76
4
3
2
1
This end of the chain is closest to the OH.
Begin numbering here.
77
4
3
2
1
3-methyl-2-butanol
78
This is the longest continuous chain that
contains an hydroxy group.
Select this chain as the parent compound.
79
4
3
5
2
1
This end of the chain is closest to the OH.
Begin numbering here.
80
4
3
5
3
2
1
2
3-methyl-2-pentanol
81
EXAMPLE
  • 1) Longest carbon chain 4 carbons

  • root name butanol
  • 2) Position of OH group second carbon atom

  • 2-butanol
  • 3) Name of substituents 1-bromo

  • 3-methyl

  • 3-methyl
  • COMPLETE IUPAC NAME 1-bromo-3,3-dimethyl-2-butan
    ol

82
EXAMPLES OF POLYHYDROXY ALCOHOL
83
Ethers
  • An ether has the formula ROR.
  • R and R can be the same or different groups.
  • R and R can be saturated, unsaturated or
    aromatic.
  • Saturated ethers have little chemical reactivity
    but are often used as solvents.

84
  • Alcohols and ethers are isomeric.
  • They have the same molecular formula but
    different structural formulas.
  • An alcohol and its isomeric ether have different
    chemical and physical properties.

85
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86
Naming Ethers
87
Common Names
  • Common names of ethers are formed from the names
    of the groups attached to the carbon atom in
    alphabetical order followed by the word ether.

CH3CH2CH2 O CH2CH3
propyl
ethyl
ether
ethyl propyl ether
88
IUPAC RULES
  • RO is an alkoxy group.
  • Ethers are named as alkoxy derivatives of the
    longest carbon-carbon chain in the molecule

89
IUPAC RULES
  1. Select the longest carbon-carbon chain and label
    it with the name of the corresponding alkane.
  2. Change the yl ending of the other hydrocarbon
    group to oxy to obtain the alkoxy group name.
  3. Combine the names from steps 1 and 2, giving the
    alkoxy name first, to form the ether name.

90
This is the longest carbon-carbon chain.
Label it with the name of the corresponding
alkane.
Change the name of the other hydrocarbon group to
oxy.
CH3CH2CH2 O CH2CH3
ethyl
propane
IUPAC name ethoxypropane Trivial name ethyl
propyl ether
91
ALDEHYDES AND KETONES
  • Functional group carbonyl group
  • Aldehyde one hydrogen atom is bonded to the
    carbon in the carbonyl group.
  • Ketone the carbon atom in the carbonyl group is
    bonded to two hydrocarbon groups.

92
Naming Aldehydes
93
The IUPAC names of aldehydes are obtained by
dropping the e and adding -al to the name of
the parent hydrocarbon.
butane
butanal
al
94
  • The parent hydrocarbon is the longest chain that
    carries the CHO group.
  • This chain has 4 carbon atoms.

3
2
1
4
95
  • The parent hydrocarbon is the longest chain that
    carries the CHO group.
  • This chain has 5 carbon atoms.

4
3
2
5
1
96
4
3
2
5
3-methylpentanal
97
  • The common names of aldehydes are derived from
    the common names of the carboxylic acids.
  • The ic acid or oic acid ending of the acid name
    is dropped and is replaced with the suffix
    aldehyde.

butyric acid
butyraldehyde
98
Naming Ketones
99
  • The IUPAC name of a ketone is derived from the
    name of the alkane corresponding to the longest
    carbon chain that contains the ketone-carbonyl
    group.
  • The parent name is formed by changing the e
    ending of the alkane to -one.

propane
propanone
one
100
  • If the carbon chain is longer than 4 carbons,
    its numbered so that the carbonyl carbon has the
    smallest number possible, and this number is
    prefixed to the name of the ketone.

101
4
3
2
1
5
6
3-hexanone
102
  • The common names of ketones are derived by naming
    the alkyl or aryl groups attached to the carbonyl
    carbon followed by the word ketone.

ethyl
propyl
ethyl propyl ketone
103
ALKYL HALIDES
  • General formula CnH2n1X where n 1,2, and X
    (halogen)
  • Functional group halogen, -X (X F, Cl, Br, I)
  • Naming alkyl halides
  • - same as nomenclature of alkanes

104
AMINES
  • Amines are organic compounds and functional
    groups that contain a basic nitrogen atom with a
    lone pair
  • Functional group
  • Classification of amines

Primary amine Secondary amine Tertiary amine
                                                                                            
105
  • Primary (1o) amine one hydrogen of ammonia is
    replaced by an alkyl or aryl group
  • Secondary (2o) amine two hydrogens of ammonia is
    replaced by an alkyl or aryl group
  • Tertiary (3o) amine three hydrogens of ammonia
    is replaced by an alkyl or aryl group
  • Quaternary (4o) amine an ion in which nitrogen
    is bonded to four alkyl or aryl groups and bears
    a positive charge

106
NAMING AMINES
  • Common names
  • - formed from the names of the alkyl groups
    bonded to nitrogen, followed by the suffix
    amine.
  • - the prefixes di-, tri-, and tetra- are used to
    decribe two, three or four identical substituents.

107
NAMING AMINES
  • IUPAC names
  • - similar to that alcohols.
  • - the longest continuous chain of carbon atoms
    determine the root name.
  • - the e in alkane name is changed to amine,
    and a number shows the position of the amino
    group along the chain.
  • - other substituents on the carbon chain are
    given numbers, and the prefix N- is used for each
    substituent on nitrogen.

108
CARBOXYLIC ACIDS
  • Functional group carboxyl group, -COOH
  • The carboxyl group can also be written as

or
109
  • Open-chain carboxylic acids form a homologous
    series.
  • The carbonyl group ( ) is always at
    the beginning of a carbon chain.
  • The carbonyl carbon atom is always designated as
    C-1.

3
2
1
110
  • The IUPAC name of a carboxylic acid is derived
    from the name of the alkane corresponding to the
    longest carbon chain that contains the carboxyl
    group.
  • The parent name is formed by changing the e
    ending of the alkane to oic acid.

methanone
oic acid
111
Examples of carboxylic acid
112
  • Organic acids are usually known by common names.
  • These names usually refer to a natural source of
    the acid.

ethanoic acid
methanoic acid
IUPAC name
IUPAC name
113
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114
CARBOXYLIC ACID DERIVATIVES
Group replacing the OH group of RCOOH Class of compound General formula Example
-X (halogen) Acyl halide
-OR Ester
-NH2 Amide
Acid anhydride
115
Esters
116
An ester is an organic compound derived from a
carboxylic acid and an alcohol.
carbonyl group
OR bonded to a carbonyl carbon.
117
Esterification is the reaction of an acid and an
alcohol to form an ester.
acetic acid(ethanoic acid)
ethyl alcohol(ethanol)
ethyl acetate(ethyl ethanoate)
118
IUPAC NAME
  • According to the IUPAC system the alcohol part of
    the ester (R?) is named first.

119
IUPAC NAME
  • This is followed by the name of the acid where
    the ic ending of the acid has been changed to
    ate.

120
IUPAC NAME
  • According to the IUPAC system the alcohol part of
    the ester (R?) is named first.
  • This is followed by the name of the acid where
    the ic ending of the acid has been changed to
    ate.

ethyl ethanoate
121
  • COMMON NAME
  • The alcohol part is named first (derived from the
    common names of alcohol).
  • The common names of esters are derived by adding
    ate to the name of the acid.

acetate
acetic acid ?
ethyl
122
  • COMMON NAME
  • The alcohol part is named first (derived from the
    common names of alcohol).
  • The common names of esters are derived by adding
    ate to the name of the acid.

ethyl acetate
123
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124
Amide
  • Amide a composite of a carboxylic acid and
    ammonia or an amine.
  • Classification of amide
  • i) primary amide RCONH2 (two H atoms bonded to
    N atom)
  • ii) secondary amide RCONHR (one H atoms
  • bonded to N atom)
  • iii) tertiary amide RCONRR (no H atoms bonded
    to N atom)

125
NAMING AMIDE
  • IUPAC name
  • i) primary amide
  • - first name the corresponding acid. Drop the
    ic acid or oic acid, and add the suffix amide.

ammonia
ethanoic acid
ethanamide
IUPAC name
acetic acid
acetamide
Common name
126
NAMING AMIDE
  • IUPAC name
  • i) secondary and tertiary amide
  • - treat the alkyl groups on nitrogen as
    substituents, and specify their position by the
    prefix N-.

127
Acyl halide / acid halides
  • Naming acid halides
  • - replacing the ic acid suffix of the acid name
    with yl and the halide name.

128
Acid anhydride
  • Naming acid anhydride
  • - the word acid is changed to anhydride in both
    the common and the IUPAC name

129
FUNCTIONAL GROUPS OF ORGANIC COMPOUNDS
130
POLYMERS
  • A polymer is a high molar mass molecular
    compound made up of many repeating chemical units.
  • Naturally occurring polymers
  • Proteins
  • Nucleic acids
  • Cellulose
  • Rubber
  • Synthetic polymers
  • Nylon
  • Dacron
  • Lucite

131
  • The simple repeating unit of a polymer is the
    monomer.
  • Homopolymer is a polymer made up of only one
    type of monomer

132
  • Copolymer is a polymer made up of two or more
    monomers

Styrene-butadiene rubber
133
Formation of Polyethylene
ethylene monomer
nCH2CH2 ?
CH2 CH2CH2 CH2n CH2 CH2 CH2 CH3
  • n the number of monomer units.
  • n ranges from 2,500 to 25,000

134
SOME MONOMERS AND THEIR COMMON SYNTHETIC POLYMERS
135
USES AND IMPORTANCE OF ORGANIC COMPOUNDS
  • NYLON
  • Nylons are condensation copolymers formed by
    reacting equal parts of a diamine and a
    dicarboxylic acids, so that peptide bonds form at
    both ends of each monomer in a process analogous
    to polypeptides biopolymers.
  • General reactions

Nylon
Diamines
Dicarboxylic acids
136
Basic concepts of nylon production
  • The first approach
  • combining molecules with an acid (COOH) group on
    each end are reacted with two chemicals that
    contain amine (NH2) groups on each end.
  • Form nylon 6,6, made of hexamethylene diamine
    with six carbon atoms and acidipic acid, as well
    as six carbon atoms.
  • The second approach
  • a compound has an acid at one end and an amine
    at the other and is polymerized to form a chain
    with repeating units of (-NH-CH2n-CO-)x.
  • Form nylon 6, made from a single six-carbon
    substance called caprolactam.

137
Uses and important of nylon
  • Apparel Blouses, dresses, foundation garments,
    hosiery, lingerie, raincoats, ski apparel,
    windbreakers, swimwear, and cycle wear
  • Home Furnishings Bedspreads, carpets, curtains,
    upholstery
  • Industrial and Other Uses Tire cord, hoses,
    conveyer and seat belts, parachutes, racket
    strings, ropes and nets, sleeping bags,
    tarpaulins, tents, thread, monofilament fishing
    line, dental floss


138
AZO-DYES
  • Azo compounds
  • - compounds bearing the functional group
    R-NN-R',
  • in which R and R' can be either aryl or
    alkyl.
  • - NN group is called an azo group
  • - HNNH is called diimide
  • Aryl azo compounds have vivid colors, especially
  • reds, oranges, and yellows
  • Yellow azo dye

139
Uses and important of azo dye
  • Methyl orange - used as acid-base indicators due
    to the different colors of their acid and salt
    forms
  • Artists paints clays, yellow to red range
  • Dye in food and textiles

140
E102 Tartrazine                                       
E107 Yellow 2G                                                                
E110 Sunset Yellow                                         
E122 Azorubine                                       
EXAMPLES OF AZO DYES USED IN FOOD
141
E123 Amaranth                                       
E124 Ponceau 4R                                 
E129 Allura Red                              
E151 Brilliant Black                                                           
142
FUEL
  • Any material that is burned or altered to obtain
    energy and to heat or to move an object
  • Its energy can be stored to be released only when
    needed, and that the release is controlled in
    such a way that the energy can be harnessed to
    produce work
  • Examples Methane, petrol and oil.
  • Application of energy released from fuels
  • - cooking
  • - powering weapons to combustion
  • - generation of electricity
  • Fuel oil generate heat or used in an engine for
    the generation of power
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