SCH 2108: CHEMISTRY II

LECTURE NOTES
Dr. Moses A Ollengo
Chemistry Department,
Dedan Kimathi University of Technology

ORGANIC CHEMISTRY

Organic chemistry covers a large class of molecules, all of which contain carbon and hydrogen.
Other elements can also be found in molecules that are considered to be organic, such as
nitrogen, oxygen, sulfur, and phosphorous.

Unique properties of Carbon

1. Carbon is tetravalent i.e it has four valence electrons and therefore can form four strong
covalent bonds with other carbon atoms or other elements (H2, N2, S, Br etc.). Eg CH4

The arrangement of atoms, which is a tetrahedron with angles of 109.5° between

hydrogens.
The arrangement in space about the central carbon can be explained in very simple terms.
Each covalent bond contains two electrons and constitutes a region of negative charge.
Since four such regions in space must repel one another, they will be as far apart as
possible and this puts the hydrogens at the corners of a tetrahedron.
2. Catenation is the ability of carbon to form very long chains of interconnecting C-C
bonds.
Carbon-carbon bonds are strong, and stable and this property allows carbon to form an
almost infinite number of compounds; in fact, there are more known carbon-containing
compounds than all the compounds of the other chemical elements combined except
those of hydrogen (because almost all organic compounds contain hydrogen as well).

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 CH3-CH2- CH2-CH2-CH2-CH2-CH3
3. Carbon can form multiple bonds including double (alkenes –C=C-), or triple bonds with
other carbon atoms (alkynes –C=C-) or other elements e.g Nitrogen.

4. Carbon can also form an enormous variety branched compounds and rings of various
sizes.

Hydrocarbons
Hydrocarbons are compounds composed only of carbon and hydrogen atoms.
Hydrocarbons provide the backbone of all organic compounds.
Each carbon atom in a hydrocarbon forms a total of four bonds.
These bonds are combinations of single bonds with hydrogen atoms and single or multiple bonds
with other carbon atoms.
Hydrocarbons are classified into alkanes (carbon atoms in the structure are joined by single
bonds), alkenes (at least two carbon atoms in the structure are joined by a double bond), and
alkynes (at least two carbon atoms in the structure are joined by a triple bond).

Organic Compounds occur as:

• Straight chains: aliphatic
• Branched compounds
• Rings
Formulas for representation of hydrocarbons
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 i. A two-dimensional structural formula of a hydrocarbon shows all of the atoms with all of
their bonds in the plane of the page.

ii. A condensed structural formula includes all of the atoms but uses line bonds to
emphasize the main structural characteristics of the molecule. Eg., for Heptane
CH3-CH2- CH2-CH2-CH2-CH2-CH3
Taking out the lines representing the carbon-carbon bonds condenses this formula to:
CH3CH2CH2CH2CH2CH2CH3
Since heptane has five repeating —CH2— groups, called methylene groups. The formula
can be further condensed to:
CH3(CH2)5CH3
iii. Bond-line formulas represent the carbon atoms as the intersection of lines and as line
ends. You assume all the hydrogen atoms needed to complete carbon’s valences.

nonane
NOMENCLATURE OF HYDROCARBONS
Organic compounds are arranged into classes according to the particular functional groups that
they contain.
Members of each class of compounds share common chemical and physical characteristics.
The names of organic compounds are assigned according to the class of the compound as
determined by the functional groups.

IUPAC Guidelines on nomenclature of organic compounds

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Although called trivial names are known for many organic compounds, they are used
colloquially and where it is simplest.
However, a systematic nomenclature system that chemists use has been adopted by the
International Union of Pure and Applied Chemistry (IUPAC) and is internationally accepted as
the standard.
Under this system one name fits one structure, and each name identifies a structure
unambiguously.
1. A systematic name consists of three parts:
• A prefix: appears before the stem name, and indicates a substituent on the chain
(a substituent may be regarded as a group replacing hydrogen in the parent
alkane).
• A stem: identifies the longest carbon chain (parent alkane): It is the main part of
the name, or it gives an indication of the particular alkane on which the name is
based and indicates the number of carbon atoms in the longest carbon chain
present in the compound.
For rings the word “cyclo” is added before the stem name
• A suffix: identifies the type of compound and appears at the end .eg A suffix -
ane on the name of an organic compound indicates an alkane.
A suffix -ane on the name of an organic compound indicates an alkane, -ene
alkenes and -yne for alkynes
NB: Before the stem name, a prefix indicates a substituent (a substituent may be
regarded as a group replacing hydrogen in the parent alkane).
Both the nature and position of a substituent must be indicated and are included in
the name.

No of carbons Parent/stem name Alkane Ring

1C Meth Methane
2C Eth Ethane
3C Prop Propane cyclopropane
4C But Butane cyclobutane

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 5C Pent Pentane cyclopentane
6C Hex Hexane cyclohexane
7C Hept Heptane cycloheptane
8C Oct Octane cyclooctane
9C Non Nonane cyclononane
10C Dec Decane cyclodecane
11C Undec Undecane undecane
12C Dodec Dodecane cyclododecane

Common prefixes for substituents derived from alkanes

For any alkane, the corresponding group is termed an alkyl substituent.

No of carbons Prefix/substituent name name Formula

1C Methyl -CH3
2C Ethyl -CH2CH3
3C Propyl -CH2CH2CH3
4C Butyl -CH2CH2CH2CH3
5C Pentyl -CH2CH2CH2CH2CH3
6C Hexyl -CH2CH2CH2CH2CH2CH3
R-H R- -alkyl
Steps followed when naming organic Compounds
1. Give the parent name for the structre by counting the number carbons in the longest chain
or ring. Eg: longest chain 3c = propane, ring 6C = cyclohexane

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2. Number the carbon atoms along the chain to give the lowest number for the position of
the substitutuent.

3. Next name the substituent and indicate its position (by a prefix)
The name of the prefix is methyl comes from methane: it is an alkyl substituent.
Position of the prefix = 2
unambiguous name is 2-methylhexane
The compound we have named is different

3-methylhexane
4. For multiple substituents give each substituent a number to indicate its position, and
indicate the number substituents by the appropriate prefix: di: two, tri: three, tetra: four
etc.

Substituents: Methyl
No of substituents: 2
Preffix: di
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 Position: 2, 5
IUPAC name: 2,5-dimethylheptane
NB: The name is not 3,6-dimethylheptane because adding the position no on the of
substiteuents in2,5-dimethylheptane (2+5= 7) gives a lower number than in 3,6-
dimethylheptane (3+6=9)
The numbers are separated by a “comma” while a "hyphen" separates numbers from
words (i.e., the substituent and the parent alkane), words are linked and not broken with
spaces
5. When more than one substituent is present, the alphabetical order is followed; E.g.,

Longest chain: 9 carbons; nonane

Substituents and positions methyl: 3 and ethyl: 6
Name 6-ethyl-3-methylnonane
(e comes before m alphabetically)
NB: The lowest numbers are used for any possible choices
6. The multiplier "di" is not considered in the alphabetizing. Hence, the name of the
following alkane is 5-ethyl-2,3-dimethylheptane:

7. When two or more subtsituents are attached on the same carbon, the number indicating
the position is repeated in the name. E.g.,

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 The correct name is 5-ethyl-2,2-dimethylheptane (both the methyl substitutents are
attached to carbon number 2)
8. Some trivial nomenclature is retained for simple branched substituents. Eg.,

is called the isopropyl group

Examples:

4-isopropylheptane

4-isopropyl-3-methylheptane
This compound can be represented as:

other common trivially named substituents include:

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 (CH3)2CHCH2- is isobutyl

secondary-butyl (or sec-butyl); sec is an abbreviation for

secondary)

written as (CH3)3C– is tertiary-butyl or tert-butyl; tert is an

abbreviation for tertiary

Therefore trivial naming of substituents is as follows:

primary (1°): 1 carbon bonded to carbon attached to chain.

secondary (2°): 2 carbons bonded to carbon attached to chain

tertiary (3°): 3 carbons bonded to carbon attached to chain

9. When substituents are halogen atoms, the prefixes fluoro, chloro, iodo, and bromo are
used to denote the substituents. Eg.,

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 CH3CH2CH2CH2Br ; Bromobutane
10. In ring structures the prefix cyclo- indicates presence of a ring of carbon atoms.
Such compounds are termed cycloalkanes.

4 carbon ring: Cyclobutane

6 carbon ring: cyclohexane

cyclopropane

methylcyclopentane
In these examples, all carbons are identical and they are not numbered.
However, sometimes numbering is necessary to define the name unambiguously and to
assign the position bearing the substituent as 1.
Where more than one substituent is on the ring, the positions of the substituents must be
specified in the name, e.g.

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 1-ethyl-3-isopropylcyclohexane.
NB: The numbering around the ring so as to give the substituents must give the lowest
number.
Skeletal structures are more commonly used for cyclic compounds - the above examples
become:

Alternatively, hybrids of the two conventions are often used, e.g

Example: Name the following compound

ALKANES

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There are various subdivisions in the classification of hydrocarbons.
Alkanes is a family of hydrocarbons saturated hydrocarbons in which carbons atoms are
linked by single bonds.
This means that they are saturated with hydrogen, and that they do not react with hydrogen.
They are saturated because the carbon atoms are bonded to maximum no of hydrogen atom.
Also called paraffins from the Latin parum affinis, meaning "little affinity implying a lack of
reactivity).
They are also referred to as aliphatics (from the Greek word aleiphar meaning "fat or oil").
Alkanes belong to a homologus series of organic compounds in which the members differ by a
constant molecular mass of 14 that is CH2.
A homologous series is a group of organic compounds having similar structure and
similar chemical properties in which the successive compound differs by CH2 group
The general formula for alkanes is CnH2n+2. Where n= is an integer 1, 2, ……
When the carbon atoms of a hydrocarbon are linked end to end, we refer to them as being
straight chain compounds; a better description is unbranched chain to distinguish branched
chain possibilities.

The simplest compound is methane.

No of carbons Alkane General Formula Structural formula

1C Methane CH4 CH4
2C Ethane C2H6 CH3CH3
3C Propane C3H8 CH3CH2CH3
4C Butane C4H10 CH3CH2CH2CH3
5C Pentane C5H12
6C Hexane C6H14
7C Heptane C7H16
8C Octane C8H18
9C Nonane C9H20
10C Decane C10H22

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 11C Undecane
12C Dodecane

ISOMERISM
Constitutional or structural isomerism: is the existence of compounds such that they have
same molecular formula but differ from each other in the arrangement of attachment of the atoms
in the structure.
Consequently, these are molecules which are fundamentally different from each other, having
different amounts of branching in their chains or different positions of functional groups or even
possessing entirely different functional groups.
Eg., For the formula C4H10 two formulas can be obtained;

n-butane

Isobutane or 2-methylpropane
('n-' indicates a normal straight chain arrangement while the 'iso-' indicates an arrangement
containing a (CH3)2CH- group).
These isomers have differing physical and chemical properties.
Now consider the next highest member of the alkane family, pentane C5H12.
Thus CH3CH2CH2CH2CH3 is pentane or n-pentane,

isopentane

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 neopentane
These are constitutional isomers of pentane, having the same molecular formula C5H12.
Stereoisomerism: the molecules have atoms attached together in the same order, but differ from
each other in their spatial (three-dimensional) arrangement.
You will find that your understanding of this topic will be greatly helped by looking at and
building three-dimensional models of the different molecules.
There are two types of stereoisomerism:
• geometric (commonly known as cis- trans)
• optical isomers
1. Geometric isomers (cis-trans isomers)
When there is some constraint in a molecule that restricts the free rotation of bonded
groups, they become fixed in space relative to each other.
Where there are two different groups attached to each of the two carbon atoms that have
restricted rotation, this gives rise to two different three-dimensional arrangements of the
atoms known as geometric isomers.
The restriction on rotation can be caused by a double bond or a cyclic structure as shown
below.
Cis- refers to the isomer that has the same groups on the same side of the double bond or
ring,
trans- is the isomer that has the same groups on opposite sides, or across the point of
restricted rotation.

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These prefixes are given in italics before the name of the compound.
Examples

2. Optical isomers: are molecules that differ three-dimensionally by the placement of

substituents around one or more atoms in a molecule.
Optical isomers were given their name because they were first able to be distinguished by
how they rotated plane-polarized light.
These molecules are not necessarily locked into their positions, but cannot be converted
into one another, even by a rotation around a single bond.
For example, consider the following two molecules.

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In the molecule on the left, the chlorine is oriented upward, and in the molecule on the right, the
chlorine is oriented downward.
(These molecules are presented in Wedge-Dash Notation).

CYCLOALKANES
In ring structures the prefix cyclo- indicates presence of a ring of carbon atoms are formed when
terminal carbon atoms in a straight or branched alkane are joined.
These have the general formula CnH2n. Examples are:
cyclobutane formed from butane:

Cyclohexane formed from hexane:

Physical properties of alkanes and cycloalkanes:

Alkanes are colourless
They are water-insoluble.

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Their boiling point increases with increase in molecular weight, e.g.

1-4 C: Gaese
5-16C: liquids
>18C: solids
Unbranched hydrocarbons have higher boiling points than their branched isomers.
For example:

n-pentane 2,2-dimethylpropane
The unbranched chain alkanes can align themselves more closely, and hence develop stronger
intermolecular forces and associations than are possible when branching of the chain is present.
The greater the association between the molecules, the higher the boiling point

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Chemical properties of alkanes and cycloalkanes:
As their alternative name 'paraffin' implies, alkanes are inert to most common chemical reagents,
including:
• Strong acids
• Strong alkalis
• Oxidising agents (under normal laboratory conditions)
• Halogens (in the dark)
Candle wax and petroleum jelly (Vaseline) are common two high formula weight alkanic
compounds Apart from their combustibility they are very stable and unreactive chemicals.

i. Combustion
It is an oxidation reaction involving burning of substances in air.
The combustion (burning) of alkanes produces water (steam) and CO2 and heat.

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Similar equations can be written for petrol, which is being oxidised in enormous quantities daily
in internal combustion engines.
Petrol consists mainly of a complex and variable (depending on its source) mixture of alkanes.
While complete combustion of petrol would normally form just carbon dioxide and water,
limited oxygen supplies leads to incomplete combustion and the formation of the toxic gas
carbon monoxide and carbon (soot).

ii. Heating alkanes at high temp in presence of a catalyst results in alkenes. E.g.

iii. Cracking of alkanes

Cracking is the breaking up large hydrocarbon molecules into smaller molecules.
This is achieved by using high pressures and temperatures without a catalyst, or lower
temperatures and pressures in the presence of a catalyst.
The source of the large hydrocarbon molecules is often the naphtha fraction or the gas oil
fraction from the fractional distillation of crude oil (petroleum).
These fractions are obtained from the distillation process as liquids, but are re-vaporised
before cracking.

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 The hydrocarbon molecules are broken up randomly to produce mixtures of smaller
hydrocarbons, some of which have carbon-carbon double bonds.
One possible reaction involving the hydrocarbon C15H32 might be:

iv. Reaction with halogens

Alkanes react with halogens when heated or in the presence of visible light to form
haloalkanes
E.g., methane, reacts with chlorine when heated or in the presence of visible light:

This reaction (and the oxidation reactions) needs the input of energy either electrical, thermal, or
radiant energy.
After the first hydrogen atom has been replaced, the reaction can proceed further:

Molecular fluorine, bromine and iodine can undergo the same reaction with light but F2 is
explosively reactive and I2 barely reacts at all.
Chlorine will also react by the same mechanism with other alkanes. For
example with ethane:

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All the hydrogens in ethane are identical, therefore only one product is formed, but with further
reaction the hydrogens are not identical, and the product formed will depend on which hydrogen
is replaced.

Therefore two products are obtained, CH3CHCl2 (1,1-dichloroethane) and ClCH2CH2Cl (1,2-
dichloroethane).
These dichloroethanes are constitutional isomers.
For propane, the first halogenation step gives the possibility of two isomeric products:

Bromine is said to be regioselective in this reaction, preferring to replace the secondary

hydrogen much more than a primary hydrogen (a regioselective reaction is a reaction in which
one region of the molecule is more reactive than another, thus leading to selective product
formation).
In this reaction, two different types of C–H bonds are broken and the relative amounts of product
are dependent upon three factors:
i. The ease with which the different kinds of hydrogens react with the halogen;
ii. The number of each kind of hydrogen in the molecule: the more hydrogens there are of
any one type, the greater is the probability of the halogens reacting with them.

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 iii. The type of halogen.
Thus the chlorine atom has greater chance of colliding with a primary hydrogen than a
secondary, so that more 1-chloropropane should be produced. Not only is collision between
molecules of importance, but collision between certain parts of molecules can also have
relevance in the course of a reaction.
An organic reaction involves:
• breaking of bonds
• Formation of bonds
These bonds are covalent; electron pairs are involved
It is the sequence in which bond breaking and bond formation occurs as well as how the energy
of the system changes during a process which defines the mechanism of a reaction.
Uses of alkanes
i. Heating
ii. electricity generation
iii. Cooking
iv. production of polymers
v. serve as intermediates in the synthesis of drugs and pesticides
vi. components of gasoline (pentane and octane)
vii. paraffin wax

Uses of Alkanes According to Number of Carbon Atom

1. The first four alkanes are gases and are used for heating, cooking and electricity
generation.
• The main components of natural gas are methane and ethane.
Propane and Butane are used as LPG (liquefied petroleum gas).
• Propane is also used in the propane gas burner, butane in disposable cigarette
lighters.
• They are also used as propellants in Aerosol sprays.
2. Alkane having carbon number 5-8 are volatile liquids.
• They are used as fuels

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 • They are also used as solvents for nonpolar substances.
3. Alkanes from having carbon 9-16 form the major part of Diesel and aviation fuel.
4. Alkanes from 17 carbon upwards (solids) form the most important components of Fuel
oil and lubricating oil also used as anti-corrosive agents, as their hydrophobic nature
means that water cannot reach the metal surface.
Many solid alkanes find use as paraffin wax.
5. Alkanes with 35 or more carbon atoms are used for road surfacing.
6. Synthetic Polymers such as polyehtylene are alkanes with chains containing hundreds of
thousands of carbon atoms.

Sources of alkanes: the two major sources of alkanes are natural gas and petroleum.
Natural gas consists of approximately 90 to 95% methane, 5 to 10% ethane, and a
mixture of other relatively low-boiling alkanes (propane, butane and 2-methylpropane).
Petroleum is a thick, viscous, liquid mixture of thousands of compounds, most of them
hydrocarbons, formed by the decomposition of marine plants and animals.
The fundamental separation process in refining petroleum is fractional distillation.
All crude petroleum that enters a refinery goes to distillation units, where it is heated to
temperatures as high as 370 to 425°C and separated into fractions.

FUNCTIONAL GROUPS
Functional group: an atom or group of atoms within a molecule that shows a characteristic set
of predictable physical and chemical behaviors. They are they are centers of chemical reactivity.
Functional groups are important in organic chemistry because:
a) They are sites predictable chemical behavior. A particular functional group, in whatever
compound it is found, undergo the same types of chemical reactions.
b) Determine in large measure the physical properties of a molecule.
c) Serve as the units by which we classify organic compounds into families.
d) Serve as a basis for naming organic compounds.
Examples
Alkene: defined by the C-C double bond

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Benzene Ring: a special ring of carbons with alternating single and double bonds, has a special
degree o f stability

Alcohol: characterized by the hydroxy, –OH group. It is a very important group in

monosaccharides (carbohydrates).

Sulfide: carbon groups bounded to a sulfur atom

Alkyne: defined by the C-C triple bond

Alkyl Halide: haloalkane, replace X in the drawing with a halogen from the periodic table; when
drawing a haloalkane be sure to not forget the lone pairs on X.

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Ether: defined by an oxygen bounded to two carbons. The functional group of ethers can
conform to many different functions, making it an important character in synthetic
transformations

Amine: a carbon molecule bound to a nitrogen. The nitrogen typically has a lone pair of
electrons.

Ketone: defined by a carbon double bound to an oxygen (different than an aldehyde because it
can only be found in the inside of a molecular chain- the carbon does not have to be attached to a
hydrogen). Ketones, aldehydes, and carboxylic acids contain the carbonyl functional group: C
double bound to O.

Aldehyde: defined by a carbon double bound to an oxygen and single bound to hydrogen;
because it is characterized by a bond to hydrogen, it can only be found at the ends of molecular
chains

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Carboxylic Acid: characterized by the carboxyl group; RCO2H (R being any subset of a
molecule); any molecular chain bound to a carbon, this carbon has a double bond to oxygen and
also attached to an alcohol group

Ester: RCO2R (R being any subset of a molecule)

Amide: contains the double bond between a carbon and an oxygen, the carbon is also bonded to
a nitrogen

Imine:

Nitrile:

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Acid Chlorine:

UNSATURATED HYDROCARBONS
Unsaturated Hydrocarbons — contain carbon- carbon double or triple bonds (more
hydrogens can be added).

ALKENES
Alkene: an unsaturated hydrocarbon that contains one or more carbon-carbon double bonds.
The molecular formula of this group is CnH2n (n is the number of carbon atoms).
Alkenes belong to a homologus series of organic compounds in which the members differ by a
constant molecular mass of 14 that is CH2.
The Suffix = -ene is added to the prefix indicating the longest carbon chain.
Alkenes have less hydrogen atoms than alkanes.
C2H4, CH2=CH2, CH2=CH-CH3
In the carbon-carbon double bond, two pairs of electrons are being shared, leaving the carbon
free to bond to two other atoms.
CH2CH2 ethylene, C2H4
CH2CHCH3 propylene, C3H6

IUPAC Nomenclature of Alkenes

1. Step 1. Identify and name the longest continuous chain of C atoms which contains the
double bond(s) (No of C +-ene).
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 2. Step 2. Number the longest chain so that the C’s joined by the double bond have the
lowest numbers possible.
3. If the double bond has the same position starting from either end, use the positions of the
substituents to determine beginning of the chain.
4. Step 3. Locate the double bond by the lower- numbered carbon atom joined by the
double bond (e.g., 1-butene).
5. Step 4. Locate and name attached groups.
6. Step 5. Combine the names for the attached groups and the longest chain into the name.

7.
Example 1: Provide the IUPAC names for the following compounds

8. If there is more than one double bond: – a counting prefix (di-, tri-, tetra-, etc.) is placed
immediately in front of the suffix -ene to indicate the number of double bonds (diene,
triene, tetraene, etc.).
9. Usually, an “a” is placed before the counting prefix to make pronunciation easier (e.g.,
butadiene). – The starting position of each double bond is indicated by the lower number,
separated by commas (e.g., 1,3-butadiene).
10. For cycloalkenes, the ring is named as cyclo- + no of C + -ene; one of the carbons of the
double bond must be numbered “1.”

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Example 2: Provide the IUPAC names for the following compounds

Example 3: Draw structural formulas for the following molecules:

• 2-methyl-2-butene
• 4-methyl-1-pentene
• 2-methyl-3-pentene (what’s wrong with this name?)
• 4-ethyl-3-hexene (what’s wrong with this name?)
• 2,3,4-trimethyl-1,3-pentadiene
• 1,6-dimethylcyclohexene
• 5-ethyl-1,3-cyclopentadiene
Bonding in Ethylene
When two sp2-hybridized carbons are next to each other, two kinds of orbital overlap take
place:
• end-on-end overlap of the sp2 orbitals to make a σ-bond (sigma bond).
• side-to-side overlap of the unhybridized p orbitals to make a π-bond (pi bond).

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 Because of the π-bond, free rotation is not possible around carbon-carbon double bonds.

The Shape of the Ethylene Molecule•

Since each carbon in the double bond is trigonal planar in shape, the entire ethylene
molecule is a flat molecule, with the atoms separated by bond angles of 120°.

Exercise:
1. Are the following molecules geometric isomers of each other, or are they the same
molecule?

2. Draw the two geometric isomers of the following molecule: CHClCHCH3

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 3. Which of the following molecules are structural isomers of each other, which are
geometric isomers of each other, and which are the same molecule?

4. provide IUPAC names for the following molecules:

5. Draw structural formulas for the following molecules:

• cis-2-pentene
• trans-3-methyl-3-hexene
Some Important Alkenes

Name Structure Uses

Ethylene (ethene) Used in the manufacture of the
plastic polyethylene.
The release of ethylene stimulates the
beginning of the ripening process in
many plants; some plants can be
picked while unripe (when they are
less fragile), and exposed to ethylene
gas to cause ripening once they reach

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 their destination
Propylene Produced in the cracking of
(propene) petroleum;
used in the manufacture of the plastic
polypropylene.

Vinyl chloride A carcinogenic gas manufactured

(chloroethene) from ethylene;
used in the manufacture of the plastic
polyvinyl chloride (PVC).

Tetrachloroethyl Better known as perchloroethylene

ene (“Perc”);
a non- flammable organic solvent,
widely used in dry cleaning;
it is also used as an industrial solvent,
degreaser, and paint remover.
A red pigment found in tomatoes,
watermelon, guava, papaya, pink
grapefruit, apricots, and rosehips;
lycopene is a good antioxidant, and is
more readily absorbed from cooked
tomatoes and tomato paste, especially
if the foods contain fat.
Zeaxanthin: A yellow pigment found
in corn, egg yolk, orange juice,
mangoes; also contributes to the
yellowish color of animal fats.
It is also found in the macula region
of the retina (macula lutea, “yellow
spot”), where it filters out some blue

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 and UV light, acting like internal
sunglasses; macular degeneration is
the most common cause of blindness
in the elderly
Terpenes and Terpenes and Essential Oils Terpenes
Essential Oils are a diverse group of molecules
which are biologically synthesized
from isoprene units. They are found
in many plants, and often have
distinctive flavors and aromas. They
are often components of essential
oils, so named because they have a
characteristic “essence” or fragrance.
Many of these molecules are
components of common foods and
perfumes. (Lycopene and its related
compounds are also terpenes.)
A fat-soluble vitamin; a metabolic
product of carotene, found in liver,
egg yolks, butter, and milk.
It combines with the protein opsin to
form rhodopsin, the primary light-
gathering pigment in vertebrate
retinas;
also involved in cell growth and
maintenance of healthy skin tissue.

Physical and Chemical Properties of Alkenes

Physical Properties of Alkenes
Many of the physical properties of alkenes are similar to those of alkanes.

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 • Alkenes are nonpolar compounds.
• They are insoluble in water.
• They are soluble in nonpolar solvents.
• They are less dense than water.
• Range of physical states: – ≤ 4 C's — gases – 5 - 17 C's — liquids – ≥ 18 C's — solids •

The chemical properties of alkenes

These are completely different from those of alkanes.
1. Addition Reaction: Most reactions of alkenes can be classified as addition reactions, in
which both parts of a reactant are added to the carbon-carbon double bond:

a) Combustion:Just like all hydrocarbons alkenes burn in the presence of oxygen to

give CO2 water and Energy
CH2CH2 + O2 → H2O + CO2 + Heat

b) Halogenation of Alkenes
In a halogenation reaction, an alkene reacts with a halogen molecule to form an
alkylhalide (haloalkane). Eg., An alkene reacts with molecular bromine (Br2) or chlorine
(Cl2) to form an alkyl halide (or haloalkane).

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The addition reaction with bromine is a useful qualitative test for the presence of double bonds.
A solution of bromine in carbon tetrachloride is red, whereas alkenes and bromoalkanes are
usually colorless.
As the bromine adds to the double bond, the red color disappears, a result providing a simple test
for the presence of double bonds.

A solution of bromine in carbon tetrachloride is red.

Solutions of alkenes and bromoalkanes are usually colorless.
As the bromine adds to the double bond, the red color disappears, a result providing a simple test
for the presence of double bonds.
c) Hydrogenation of Alkenes
In a hydrogenation reaction, is an addition reaction in which a hydrogen atom is added to each
carbon of the double bond, converting the alkene into an alkane.
The reaction only takes place in the presence of a metal catalyst (usually Pt).
35
This same process is used to produce hydrogenated vegetable oils such as margarine.

d) Addition of Acids
Acids (HF, HCl, HBr, and HI) can add to a double bond to produce an alkyl halide.

If the alkene is unsymmetrical, there are two possible products in this kind of reaction:

The major product of the reaction is predicted using Markonikov’s Rule:

Markonikov’s Rule (Vladimir Markonikov, 1869): when a molecule of the form H-X adds to a
double bond, the hydrogen becomes attached to the carbon atom that is already bonded to the
most hydrogen atoms. (“The rich get richer”)
In the example above 1-bromopropane will be the major product.
Addition of a hydrogen halide, HX, where X is a halogen:
36
Exercise:
Complete the following reactions and indicate the major product in each case.

e) Hydration of Alkenes
In a hydration reaction, the elements of water are added to an alkene, producing an alcohol as
the product in the presence of a strong acid catalyst (usually H2SO4)

37
This reaction also follows Markonikov’s rule if the alkene is unsymmetrical.

Exercise: Complete the following reactions:

38
 f) Polymerization: Polymerization is the process of binding a number of molecules which
contain a small number of Carbon atoms (Monomer) to form one molecule of a large
number of Carbon atoms (Polymer).
Monomers are small, single molecules, such as hydrocarbons and amino acids which
combine together chemically to form long chains or large 3D molecules..

In addition polymers, every atom in the reacting molecules becomes incorporated into the
resulting polymer molecule.
In most addition polymers, the monomer contains a double bond.
39
 i. Manufacture of polyethene

n = 10,000 - 30,000 = low-density polyethylenes (LDPE)

n = 10,000 - 50,000 = high-density polyethylenes (HDPE)
n = up to 200,000 = ultrahigh-molecular-weight polyethylenes (UHMWPEs)
Polyethylene is useful in food storage containers, plastic wraps and films, garbage bags,
insulation for electrical wiring, squeeze bottles, etc.
ii. Manufacture of polypropene from propene or propylene

Polypropylene (PP) forms a more orderly polymer than polyethylene, and is much harder, and is
stable at higher temperatures (which make it possible to use in sterilizable storage containers).
It is used in fibers, indoor-outdoor carpets, bottles, artificial turf, etc.

ALKYNES
Alkynes: an unsaturated hydrocarbon that contains one or more carbon-carbon triple bonds.
The molecular formula of this group is CnH2n-2 for one triple bond in the structure (n is the
number of carbon atoms).
Alkynes have less hydrogen atoms than alkanes and alkenes.
40
Nomenclature of alkynes
The nomenclature system for alkynes is identical to that of alkenes, except the suffix -yne is used
to indicate the triple bond.
The suffix -yne is used to indicate an alkyne.
Examples:

Ethyne (acetylene)

butyne

Acetylene is a colorless gas, which is produced primarily from petroleum.

It is used in oxyacetylene torches, which produce relatively high temperatures.
Acetylene also is used as the starting material for a number of plastics.
Acetylene can also be produced by the reaction of calcium carbide and water described by

Bonding in Acetylene
• When two sp-hybridized carbons are next to each other, three orbital overlaps take place:
– end-on-end overlap of the sp orbitals to make a σ- bond.
– side-to-side overlap of both sets of unhybridized p orbitals to make two π-bonds.
Because of the π-bonds, free rotation is not possible around carbon-carbon triple bonds.

41
Since each carbon in the double bond is linear in space, the entire acetylene molecule is a linear
molecule.

Besides the combustion reaction that all hydrocarbons undergo, acetylene and other alkynes
undergo the same type of addition reactions as alkenes do.
For example, let’s consider the product when HCl(g) reacts with C2H2(g).
The reaction can be broken down into two steps.

42
 AROMATIC COMPOUNDS
• Aromatic compounds are those that contain the benzene ring (C6H6) or its structural
relatives.
• Aliphatic compounds do not contain benzene rings.

The Structure of Benzene

• Although the formula indicates the presence of double bonds, benzene does not undergo the
typical alkene reactions.
• The ring structure of benzene was proposed by August Kekulé in 1865; he suggested that the
double bonds switch positions to give two equivalent.

The Resonance Structures of Benzene

In reality, the double bonds and single bonds in benzene do not change position.
The two Kekulé structures for benzene are resonance structures, meaning that each individual
structure is fictitious.
The benzene ring is sometimes represented as a hexagon with a circle inside, which emphasizes
that all of the positions on the benzene ring are equivalent.

43
Nomenclature of Benzene Derivatives
• Rule 1. When a single hydrogen of the benzene ring is replaced, the compound can be named
as a derivative of benzene

Rule 2. A number of benzene derivatives are known by their common (trivial) names rather than
by their formal IUPAC names.

Rule 3. Compounds formed by replacing a hydrogen of benzene with a more complex

hydrocarbon group can be named by naming the benzene ring as the substituent, called the
phenyl group.

44
Rule 4. When two groups are attached to a benzene ring, three isomeric structures are possible:

In naming these compounds, either the ortho / meta /para prefixes may be used, or position
numbers (begin numbering at the group which comes first in alphabetical order)

45
Rule 5. When two or more groups are attached to the benzene ring, their positions can be
indicated by numbering the carbon atoms of the ring to obtain the lowest possible numbers for
the attachment positions. Groups are arranged in alphabetical order.

Exercise:
1) Provide IUPAC names for the following molecules:

2) Draw structural formulas for the following molecules:

i. meta-ethyltoluene

46
 ii. 2,5-dibromobenzoic acid
iii. para-nitrophenol
iv. 3-phenylheptane
v. Butylbenzene
vi. 1,4,5-tribromobenzene (what’s wrong with this name?)

Physical Properties of Aromatic Compounds

i. Just like alkanes and alkenes, aromatic compounds are nonpolar,
ii. They are insoluble in water (unless other substituents, such as OH groups, are present).
iii. They are also usually less dense than water.
iv. Many aromatic compounds are obtained from petroleum and coal tar.
v. Benzene and toluene are commonly used as solvents, and are the starting materials for the
synthesis of other useful organic compounds.
vi. Some foods contain aromatic compounds, which can be synthesized by some plants.
Some aromatic amino acids and vitamins are listed as essential, because we lack the
ability to synthesize them, and must obtain them from our diet.

Chemical Properties of Aromatic Compounds

Aromatic compounds are chemically stable (unlike alkenes).
They do NOT undergo addition reaction reactions like alkenes.
They undergo substitution reactions in which a hydrogen is replaced by some other group such
as nitrogen, alkyl group, amine, halogen, Oh etc..
i. Nitration of benzene: substitution of a hydrogen on a benzene ring with a nitro group in
the presence of sulphuric acid as a catalyst.
When we heat benzene or one of its derivatives with a mixture of concentrated nitric and
sulphuric acids, a nitro (-NO2) group replaces one of the hydrogen atoms bonded to the
ring.
In this reaction, sulfuric acid is a catalyst and it is added to speed up the reaction.

47
Benzene nitrobenzene

Halogenation: in the present of an iron catalyst, chlorine reacts rapidly with benzene to give
chlorobenzene and HCl.

Some Important Aromatic Compounds

48
Aromatic rings in the diet

49
Polycyclic Aromatic Hydrocarbons (PAH)•
Polycyclic aromatic hydrocarbons consist of two or more benzene rings fused together; they
produced when organic compounds are heated to high temperatures, and are present in tobacco
smoke, car exhaust, and sometimes in heavily browned foods.

ALCOHOLS
The hydroxyl group (-OH) is found in the alcohol and phenol functional groups.

50
In alcohols, a hydroxyl group is connected to a carbon atom in an aliphatic compound.
R-O
The word “alcohol” comes from the Arabic term al kohl meaning “the fine powder.”
Originally, this referred to an antimony sulfide compound used for eye shadow, which was
ground up to form a fine powder, but then later came to refer to any finely divided powder.
In the Middle Ages, this term came to mean the “essence” of anything.
When the Europeans took up alchemy in the Middle Ages, they referred to vapors from
evaporating or boiling compounds as “spirits,” since they did not believe them to be material in
the same sense that solids and liquids were.
Alchemists began referring to “spirits of wine,” and since an alcohol when it boils away seems to
powder away to nothing, they also began to refer to “alcohol of wine” and then simply “alcohol”.
In phenols, -OH is connected to a benzene ring.
(The “parent” molecule of this class is also named phenol: PhOH or C6H5OH.)

Some Common Alcohols

Methanol CH3OH
methyl alcohol (wood alcohol) ("methy" = wine, "hule" = wood)
Found in wood smoke; contributes to the bouqet of new wine;
metabolized in the body to formaldehyde and formic acid, and can cause blindness or death (> 50
mL)

Ethanol CH3CH2OH
ethyl alcohol (grain alcohol)
The acohol of alcoholic beverages; the fermentation of honey, grain, or fruit juices to yield beers
and wines was probably the first chemical reaction to be discovered; metabolized in the body to
produce acetaldehyde

51
1-propanol (n -propyl alcohol)
CH3CH2CH2O
2-propanol (isopropyl alcohol)

Rubbing alcohol is 70% isopropyl alcohol and 30% water

Nomenclature of Alcohols and Phenols

Step 1. Name the longest chain to which the hydroxyl (-OH) group is attached.
The name for this chain is obtained by dropping the final -e from the name of the hydrocarbon
parent name and adding the ending -ol.
Step 2. Number the longest chain to give the lowest possible number to the carbon bearing the
hydroxyl group.
Step 3. Locate the position of the hydroxyl group by the number of the C to which it is attached.
Step 4. Locate and name any other substituents.
Step 5. Combine the name and location for other groups, the hydroxyl group location, and the
longest chain into the final name.

Examples:
Provide acceptable IUPAC names for the following compounds.

52
Step 6. If there is more than one OH group, a counting prefix (di-, tri-, tetra-, etc.) is placed
immediately in front of the suffix -ol (diol, triol, tetraol, etc.).
The final “e” of the parent hydrocarbon is not dropped (e.g., 1,2-propanediol).
The position of each alcohol group is indicated by carbon number, separated by commas (e.g.,
1,3- butanediol).
Step 7. For cyclic alcohols, the carbon bearing the OH is numbered as “1.”
Phenols are named after the parent compound phenol; the C bearing the OH is numbered as “1.”
Exercise:
1. Provide acceptable IUPAC names for the following compounds:

2. Draw structural formulas for the following molecules:

i. 3-methyl-2-pentanol
ii. 2,4,4,5-tetramethyl-2-heptanol
iii. 1-ethyl-1-hexanol (what’s wrong with this name?)
iv. 3-ethylcyclopentanol
v. 3-ethylphenol
vi. 3-methyl-2,4-pentanediol
Classification of Alcohols
Alcohols are classified as primary (1°), secondary (2°), or tertiary (3°) according to how many
carbon groups are attached to the carbon bearing the OH group:

53
Properties of Alcohols
i. Dehydration of Alcohols to Produce Alkenes
Heating alcohols in concentrated sulfuric acid (H2SO4) at 180°C removes the OH group and a H
from an adjacent carbon to produce an alkene, with water as a by-product.
Since water is “removed” from the alcohol, this reaction is known as a dehydration reaction (or
an elimination reaction):

If there is more than one possible product of a dehydration reaction, as for an unsymmetrical
molecule, the major product can be predicted from Zaitsev’s Rule.
Zaitsev’s Rule states that when an alkene is produced in an elimination reaction, the major
product is the one with the more highly substituted double bond.

54
Dehydration of Alcohols to Produce Ethers
Heating alcohols (R-OH) in concentrated sulfuric acid (H2SO4) at 140°C removes a molecule of
water from two alcohol molecules, causing the two “R” groups to become attached to an oxygen
atom, forming an ether functional group:

Oxidation of Alcohols to Carbonyl Compounds

An oxidation reaction occurs when a molecule loses electrons and this is usually manifested as
an increase in the number of oxygen atoms or a decrease in the number of hydrogen atoms. Some
common oxidizing agents include potassium permanganate (KMnO4), chromic acid (H2CrO4),
sodium dichromate (Na2Cr2O7), and other Cr6+ salts.
Alcohols can be oxidized by removing two H atoms from the molecule and the exact products of
the reaction will depend on the type of alcohol.
55
• Primary alcohols are oxidized first to aldehydes, but the aldehydes are then usually
oxidized into carboxylic acids.

In the body, oxidation of ethanol to acetaldehyde takes place in the liver; the acetaldehyde is
further oxidized to acetyl coenzyme A, which can be used to synthesize fat or eventually be
oxidized to water and carbon dioxide.
• Secondary alcohols are oxidized to ketones, which cannot be oxidized any further:

• Tertiary alcohols, because there is by definition no hydrogen on the alcoholic carbon,

cannot be oxidized:

56
 Alcohols react with carboxylic acids in presence of conc H2SO4 (catalyst) to yield esters
(sweet smelling compounds).
CH3CH2OH + CH3CH2CH2CH2COOH → CH3CH2-O-COCH2CH2CH2CH3
Ethanol pentanoic acid ethylpentanoate
Similarities between the properties of phenol and ethanol
i. Phenol and ethanol are both hydroxy compounds as they both contain the –OH group.
ii. Both react with sodium metal producing hydrogen gas and the corresponding ethoxide
or phenoxide.
iii. Ethanol and water are miscible in all proportions. Phenol is only slightly soluble in
water. If enough phenol is added, two liquid layers are produced.
iv. Both do not react with sodium bicarbonate.

Differences between the properties of phenol and ethanol

i. Phenol is a weak acid as it partially ionizes in water while ethanol is not.
ii. Ethanol does not react with sodium hydroxide while phenol does.
iii. Ethanol will not react with bromine water under normal conditions while phenol will
decolorize bromine water and a white ppt forms.
iv. Ethanol does not react Iron(III)chloride solution while phenol reacts giving a purple-
coloured product. This test is sometimes used to test for the presence of phenol.
Aldehydes and ketones

Organic halogen compounds

57
The alkyl halides are a class of compounds with the general formula
RX; where R = alkyl group, X = halogens, F, Cl, Br and I

Methods of preparing monohalides and use chemical equations to illustrate each.

i. By direct halogenations of alkanes: (See halogenations of alkanes)

R-H + X2 R-X + HX
ii. By the addition of HX on alkenes:
RCH=CHR + HX → RCH2-CHXR
iii. By reaction of alcohols and halogen acids:

iv. By reaction of alcohols and phosphorus halides:

v. By reaction of alcohols and thionyl chloride: or Darzen's method

Simple alkyl halides mostly those with only one halogen atom are named halo alkanes:
Thus:
chloromethane is CH3Cl (methyl chloride),
bromoethane is CH3CH2Br (ethyl bromide),
2-iodopropane is CH3CHICH3 (isopropyl iodide)
1-bromo-5-chloro-2-iodohexane is BrCH2CHICH2CH2CHClCH3
3,4-dichloro-1-butene is
Note that the substituents are listed alphabetically using the lowest possible numbers just as for
alkanes.
58
Physical properties of alkyl halides:
• Except for a few of the lower molecular weight members, the alkyl halides are colourless
liquids that are heavier than water.
• boiling point increases with increasing molecular weight.
CH3Cl: -24°C; C2H5Cl: 13°C; CH3CH2CH2Cl: 46°C; CH2Cl2: 40°C;
CH3Br: 5°C; C2H5Br: 38°C; CH3CH2CH2Br: 71°C;
CHCl3: 61°C; CH3I: 42°C; C2H5I: 72°C; CH3CH2CH2I: 102°C; CCl4: 77°C.
• For isomers, just like for alkanes, chain branching results in a lower boiling point, e.g.:
CH3CH2CH2CH2Cl: 77°C; CH3CH2CHClCH3: 69 °C; (CH3)2CHCH2Cl: 69°C;
(CH3)3CCl: 51°C.
1o halide > 2o halide > 3o halide (for a given halide and alkyl group)

Chemical properties of alkyl halides

1. Alkyl iodides are the most reactive of the alkyl halides(RI>RBr>RCl>RF).
Generally alkyl fluorides are very inert (this is very useful in the case of teflon, the
polymer of tetrafluoroethene (–CF2–CF2–)n, whose chemical inertness makes it useful
not only for lining frying pans but also in the construction of apparatus used in corrosive
chemical reactions.
In fact polyfluorinated alkanes are both stable and able to dissolve oxygen and they can
even be used as artificial blood.
2. Nucleophilic substitution
Halogens are much more electronegative (electron withdrawing) than carbon (electron
reppelling) and so the electron pair of the covalent bond is more associated with the
halogen atom than the carbon atom.
This results in polarization making the carbon atom susceptible to attack by negatively
charged species (nucleophiles) and readily undergoes substitution reactions (nucleophilic
substitution).
A nucleophile is an electron-rich ion or molecule that reacts at a positive or positively
polarised centre in a molecule.

59
 They can be represented as either a negatively charged ion or a neutral, electron rich
molecule:
• Nu:– e.g. hydroxide ion, HO– or cyanide ion, CN–
• Nu: e.g. water, H2O or ammonia, NH3, each of which have a lone pair of electrons that
constitute an electron-rich region.
A nucleophilic substitution reaction of an alkyl halide involves the replacement of the
halogen atom by a suitable nucleophile.
A nucleophile is a “positive loving” species and will, itself, be negatively charged or
electron rich. An electrophile is a “negative loving” species and will, itself, be positively
charged or electron deficient.

The positive polarity at the carbon of the C-X bond attracts the electron-rich nucleophile.
The general reaction is:

The carbon-halogen bond broken liberating a halide anion (the polarity helps) and forms
a carbon-nucleophile bond.
In nucleophilic substitution, the group (or atom X in this case) that is displaced is called
the leaving group.
The reaction is depicted in "arrow" notation above.
The double-headed arrows are used to indicate the movement of electrons and not the
movement of atoms.
Some of the most commonly used strong nucleophiles are:
• HO– (as NaOH in aqueous or organic solution)
• N≡C– (as NaCN in aqueous or organic solution)
• H2N– (as NaNH2 in liquid ammonia)
• R3N: (as ammonia, R=H

60
Two weaker nucleophiles are:
• H2O (water)
• R-OH (alcohols)
Example
The reaction between bromoethane (alkyl halide) and a hydroxide or cyanide, the products are an
alcohol (ethanol) and a nitrile (propanenitrile) respectively:
CH3CH2Br + NaOH → CH3CH2OH + NaBr
CH3CH2Br + NaCN → CH3CH2C≡N + NaBr
(Note here that with the nitrile group (a carbon-nitrogen triple bond), the carbon atom is included
in the carbon count for carbon chain when naming the compound).

Free radical substitution reaction of methane by a halogen

Three step reaction
i. Initiation Cl2 molecule breaks into Cl. radicals in presence of UV light
ii. Propagation: CH4 molecule loses a H atom to form a CH3. Radical
iii. Halogenation: CH3. Radical combines with Cl. radicals to form a halo alkane; CH3Cl
In the presence of excess halogen, all hydrogens on the alkylhalide are replaced by halogen
atoms.

Cl Cl Cl + Cl (Initiation)

CH4 + Cl CH3 + HCl (Propagation)

CH3 + Cl CH3Cl

Excess halogen,

CH3Cl + Cl2 CH2Cl2 + HCl

CH2Cl2 + Cl2 CHCl3 + HCl

CHCl3 + Cl2 CCl4 + HCl

3. Action of halogen:

61
 4. Dehydrogalogenation: elimination of HX by KOHalcoholic.

5. Action of heat on halo alkanes

Uses of alkyl halides;

i. As alkylating agent i.e. to introduce alkyl group in a molecule.
ii. Lower members are used as anaesthetic agent, refrigerant and solvents.
iii. As synthetic reagent.
iv. Teflon useful for lining frying pans and in the construction of apparatus used in
corrosive chemical reactions.
v. polyfluorinated alkanes can used as artificial blood.

CARBOXYLIC ACIDS
Carboxylic acids are weak acids i.e. they do not fully ionise in solution.
Rather an equilibrium is established.
RCOOH + H2O ⇌ RCOO - + H 3O+
When naming the carboxylic acids, the suffix “oic” replaces the letter “e” at the end of the parent
chain name
Eg methanoic acid CHOOH.

62
 FUELS
Petroleum (Latin Petroleum derived from Latin word petra= rock and oleum= oil or crude oil is
a naturally occurring liquid found in formations in the Earth consisting of a complex mixture of
hydrocarbons (mostly alkanes) of various lengths.
The approximate length range is C5H12 to C18H38.
Any shorter hydrocarbons are considered natural gas or natural gas liquids, while long-chain
hydrocarbons are more viscous, and the longest chains are paraffin wax.
Crude oil may also be found in semi-solid form mixed with sand, as in the Athabasca oil sands in
Canada, where it may be referred to as crude bitumen.
Petroleum is used mostly, by volume, for producing fuel oil and gasoline (petrol), both important
"primary energy" sources.
84% by volume of the hydrocarbons present in petroleum is converted into energy-rich fuels
(petroleum-based fuels), including gasoline, diesel, jet, heating, and other fuel oils, and liquefied
petroleum gas.
In its naturally occurring form, it may contain other nonmetallic elements such as sulfur, oxygen,
and nitrogen.
Crude oil is composed of hundreds of hydrocarbon compounds ranging in size from the smallest,
methane, which has only one carbon atom, to large compounds containing 200 or more carbon
atoms.
A major portion of these compounds are paraffins, which are straight-chain hydrocarbon
compounds such as methane, ethane, and propane.
The remaining hydrocarbon compounds are either cyclic compounds called napthenes or
aromatics.
The products that are normally obtained from crude oil can be grouped as follows.
1. Volatile products
• Propane LPG (Liquid Petroleum Gas)
• Butane LPG
• Light naphtha (C5s and C6)
2. Light distillates

63
 • Gasolines
• Heavy naphtha
• Kerosene and jet fuel
3. Middle distillates
• Diesel fuel
• Heating oils
• Gas oils
4. Fuel oils
• Marine diesel
• Bunker fuels (for ships)
5. Lubricating oils
• Motor oil
• Spindle oil
• Machine oils
6. Waxes
• Food and paper coating grade
• Pharmaceutical grade
7. Bitumen
• Asphalt
• Coke
Products in these groups are produced from distillation processes and treated to meet certain
specifications.
These specifications are the result of a compromise between performance capabilities of the
product and the treating that must occur to reach these performance characteristics.
It is usually black or dark brown (although it may be yellowish or even greenish) but varies
greatly in appearance, depending on its composition.
It has become the world's most important source of energy since the mid- 1950s due to its
• high energy density
• easy transportability
• relative abundance
64
Petroleum is also the raw material for many chemical products, including
• pharmaceuticals
• solvents
• fertilizers
• pesticides
• plastics
16% not used for energy production is converted into these other materials.
Petroleum is found in porous rock formations in the upper strata of some areas of the Earth's
crust.
Known reserves of petroleum are typically estimated at around 1.2 trillion barrels without oil
sands, or 3.74 trillion barrels with oil sands.
However, oil production from oil sands is currently limited.
Consumption is currently around 84 million barrels per day, or 3.6 trillion liters per year.
Because of reservoir engineering difficulties, recoverable oil reserves are significantly less than
total oil-in-place.
At current consumption levels, and assuming that oil will be consumed only from reservoirs,
known reserves would be gone around 2039, potentially leading to a global energy crisis.
However, this ignores any new discoveries, rapidly increasing consumption in China & India,
using oil sands, using synthetic petroleum, and other factors which may extend or reduce this
estimate.

Refining of crude oil

• Crude oil is refined using fractional distillation.
• Crude oils often contain inorganic salts such as sodium chloride, magnesium chloride,
and calcium chloride in suspension or dissolved in entrained water (brine) which must be
removed before refining in order to.
i. prevent catalyst poisoning,
ii. prevent equipment corrosion,
iii. prevent fouling.
• The crude oil is heated and its vaporized components passed into a fractionating column.

65
 • As the components rise up the tower, they start to cool down and will gradually condense
back into liquid form.
• They are then tapped off.
• The larger hydrocarbons, with higher boiling points, will condense first and be tapped off
near the base of the column e.g. bitumen, wax, grease, fuel oil, diesel, etc.
• The smaller hydrocarbons, with smaller boiling points, will condense later and be tapped
off near the top of the column e.g. liquid petroleum gas, kerosene, petrol, etc.

• Catalytic reforming is a chemical process used to convert petroleum

refinery hydrocarbons, typically having low octane ratings, into high-octane liquid
products called reformates which are components of high-octane gasoline (also known
as high-octane petrol).
• Octane number is a measure of the ignition quality of gas (gasoline or petrol).

• The process re-arranges or re-structures the hydrocarbon molecules in petroleum as well

as breaking some of the molecules into smaller molecules.

• The overall effect is that the product reformate contains hydrocarbons with more complex
molecular shapes having higher octane values than the hydrocarbons in the in petroleum.

• In so doing, the process separates hydrogen atoms from the hydrocarbon molecules and
produces very significant amounts of byproduct hydrogen gas for use in a number of the
other processes involved in a modern petroleum refinery.

• Other byproducts are small amounts of methane, ethane, propane, and butanes.

Industries that use petroleum as a raw material

• Pharmaceutical industries
• Solvents manufacturing industries
• Fertilizer manufacturing industries
• Pesticide manufacturing industries
• Plastic manufacturing industries

POLYMERIZATION

66
A polymer is large molecule (macromolecule) built up by repetitive bonding (covalent) of
smaller molecules (monomers).
Polymers are formed by linking monomers through chemical reaction called polymerization.
Homopolymers: are formed from identical monomers
nA → —(A-A-A)n—
Copolymers: are formed from nonidentical monomers
n A + nB → —(A-B)n—

Types of polymers
Natural: synthesized by organisms e.g. natural rubber, natural silk, cellulose, proteins, starch
etc.
Synthetic: man-made e.g. polyethylene, polypropylene, poly-styrene, polybutadiene, nylon poly-
amides, polycarbonates, phenolics, amino resins, epoxy resins etc.
Addition polymers: are formed by combining monomers across double or triple bonds e.g.
Polyethylene and other polyolefins, Polystyrene and related vinyl polymers etc.
Condensation polymers: are formed by reactions involving loss of small groups e.g. Polyesters
and polyamides, polycarbonates, phenol (urea, melamine) – formaldehyde resins, epoxy resins
etc.
Crystalline (crystallinity, > 50%) e.g. Polyethylene (HDPE and LDPE), polypropylene
(isotactic), stretched nylon polyamides, polyoxymethylene etc. cellulose (cotton) fibre.
Amorphous (crystallinity, > 50%) e.g. Natural rubber and most synthetic rubbers,N-
alkylated(>15% alkylation) nylon polyamides, poly (methacry-lates and acrylates) poly (vinyl
acetate), polystyrene etc.
A thermoplastic, or thermosoftening plastic, is a polymer that becomes pliable or moldable
above a specific temperature, and returns to a solid state upon cooling.
Thermosetting polymer forms irreversible chemical bonds during heating.
Thermosets often do not melt, but break down and do not reform upon cooling.

Monomer Polymer

67
 Polyethylene
—(CH2−CH2)n—

polypropylene

Polyacrylonitrile
Acrylonitrile

Styrene Polystyrene

68
69
Uses of addition polymers
• polyethene is used in plastic bags and in crates
• polypropene is used in plastic tubing
• polychloroethene (polyvinylchloride) is used in waterproof clothing and records
• polyphenylethene (polystyrene) is used in packaging
• Polyethene: packaging
• Polyvinyl chloride: packaging
• Nylon: clothing
• Polystyrene: clothing, mattress

CARBOHYDRATES
Monosaccharides and disaccharides

70
Monosaccharides
Are the simplest sugars (single sugars).
Can be used for fuel.
Can be linear or cyclic.
Can be converted into other organic molecules.
Can be combined into polymers.
Examples of monosaccharides: Glucose.

Disaccharides
Double sugars
Consist of two monosaccharides
Are joined by a glycosidic linkage
Remember simple sugars are put together to form disaccharides by the process of dehydration
synthesis (condensation reaction)
Example: fructose, sucrose

PROTEINS
A protein is a chain of amino acids linked together by peptide bonds (covalent bond between the
­COO­ group of one amino acid and the ­NH3+ ­group of the next one (­CO­NH­; H2O is set free
when the bond is created).
There are 20 proteinogenic amino acids.
The general structure of an amino acid is as follows.

R is the side chain (also called residue)

The amino acid has a carboxyl­group (­COO­) and an amino group (­NH3+).

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Classification of Proteins
Proteins can be classified by their functions and by their structure (and their physical properties a
nd enzymatic mechanisms).
Examples for classification by function:
• hydrogenase:catalyses the formation of hydrogen or the reversible oxidation of hydrogen
• dehydrogenase: removes hydrogen from a molecule
• acetylase: creates acetate esters
• kinase: transfers a phosphate group from a high­energy donor molecule (e.g. ATP) to a
substrate
• phosphatase: hydrolyses1 phosphate esters
• oxidoreductase: catalyses a redox (oxidation­reduction) reaction
• polymerase: creates a new DNA or RNA strand using an existing DNA or RNA strand as
template
• isomerase: converts one isomeric form of a molecule to another

LIPIDS
A class of biological molecules (i.e., are of biological origin) defined by low solubility in water
and high solubility in non-polar solvents (such as chloroform)
They are largely hydrocarbon in composition, thus represent highly reduced forms of carbon, and
upon oxidation in metabolism, yield large amounts of energy.
Examples of lipids:
• fats and oils,
• certain vitamins & hormones,
• most non-protein membrane components.

Role of lipids:
• They store energy and protect and insulate internal organs. In human bodies they are
stored as fat cells and in animal bodies as starch.
• They are found in nerve fibers and hormones as steroids, which act as chemical
messengers.
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 • Because they are not soluble in water, a major function of lipids is to build the cell
membranes that separate the internal contents of cells from the surrounding aqueous
environment.
Lipids are divided into the four groups:
• Simple lipids (waxes, fats and oils).
• Complex lipids (glycerophospholipids).
• Steroid (Cholesterol and steroid hormones).
• Prostaglandins.
HARD AND SOFT WATER
The main causes of water hardness are dissolved compounds, particularly compounds of calcium
and magnesium.
Calcium (Ca2+) ions and magnesium (Mg2+) ions that have been leached from minerals in the
ground result in "water hardness".
These ions do not pose any health threat, but they can engage in reactions that leave insoluble
mineral deposits, such as scum rings on bathtubs and cooking vessels, or scale on industrial
boilers, which decrease the boilers' efficiency.
These deposits can make hard water unsuitable for many uses.

Advantages of hard water

• Good source of calcium for strong bones and teeth
• Most prefer the taste of hard water

Disadvantages of hard water

• Lime scale blocks pipes and reduces efficiency of kettles, washing machines.
• Wastes soap and leaves a scum which can be difficult to remove from clothing.

Methods of softening hard water

The process of removing Ca2+ and Mg2+ from the water is known as water softening.

The common methods of softening hard water include

i. Precipitation using lime (Ca(OH)2)

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 Mg2+ (aq) + Ca2+ (aq) + 2 OH-(aq) → Mg(OH)2 (s) + Ca2+ (aq)

from water from lime precipitate

Notice that Ca2+ appears on both sides of equation.

The calcium ion from lime does not actually participate in the reaction to generate insoluble
Mg(OH)2.
Hence, this ion is called a spectator ion and can be omitted from the equation.
We can write the overall reaction as the net ionic equation:

ii. Precipitation using soda ash (Na2CO3)

Ca2+ (aq) + Ca2+ (aq) + 2 CO32-(aq) → CaCO3 (s)

from water from lime from soda ash precipitate

Bicarbonate (HCO3-) remaining in the water is nontoxic and does not negatively affect
the flavor of the water.
iii. Distillation: It is effective but expensive due to energy consumption.
iv. Ion-exchange devices consist of a bed of plastic (polymer) beads covalently bound to
anion groups, such as -COO-.
The negative charge of these anions is balanced by Na+ cations attached to them.
When hard water containing Ca2+ and Mg2+ is passed through the ion exchanger, the Ca2+ and
Mg2+ ions are more attracted to the anion groups than the Na+ ions.
Hence, they replace the Na+ ions on the beads, and so the Na+ ions (which do not form scummy
residues) go into the water in place of the Ca2+ and Mg2+.

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When hard water passes through the ion exchanger, the calcium ions from the water replace the
sodium ions in the ion exchanger.
The softened water, containing sodium ions in place of calcium ions, can be collected for
household use.
Unfortunately, many people with high blood pressure or other health problems must restrict their
intake of sodium.
Because water softened by this type of ion exchange contains many sodium ions, people with
limited sodium intakes should avoid drinking water that has been softened this way.

SOAPS, NON-SOAPY DETERGENTS

Soaps are generally referred to as sodium stearate or potassium stearate
The following represent their general structure

Preparation of soaps
Soaps are prepared by saponification which is an esterification reaction between an alkali such as
KOH and NaOH and a long chain fatty acid obtained from animal fat or vegetable oils.
R-COOH + NaOH → RCOONa + H2O
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 or
R-COOH + KOH → RCOOK + H2O
Examples of acids include:
Stearic acid R= C17H35OOH
Synthetic detergents are generally referred to as sodium alkylbenzene sulfonates.
The following represent their general structure

Detergents are prepared sulfonation reaction between long chain triglycerides (fatty acids) with
conc sulphuric acid and NaOH.

Cleansing action of soaps and detergents

• The hydrophobic tails ‘burrow’ into the droplet of oil or grease.
• The hydrophilic heads are left to face the surrounding water.
• This results in the formation of a ball-like structure (a micelle).
• The non-polar substances, such as oil or grease, are held inside the ball and suspended in
water, to be washed away.

The structure of a micelle

Anaerobic and aerobic digestion

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Anaerobic digestion/treatment is a natural process in which a variety of different species of
microorganisms including bacteria convert organic wastes through a variety of intermediates into
methane gas in the absence of oxygen.

Aerobic digestion/treatment is a natural process in which a microorganisms including bacteria

decompose organic wastes through a variety of intermediates in the presence of oxygen.

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