Introduction to organic chemistry

Organic chemistry is the scientific study of the structure, properties, composition, reactions,
and synthesis of organic compounds contain carbon. An organic molecule is one which contains
carbon, although not all compounds that contain carbon are organic molecules. Carbon
monoxide (CO),carbon dioxide (CO2), carbonates (e.g. CaCO3),and cyanides (NaCN) are not
organic compounds. Pure carbon compounds such as diamond and graphite are also not
organic compounds.

The study of the structure of organic compounds determines their chemical

composition and formula, while a study of their properties focuses on physical and chemical
properties, and evaluation of chemical reactivity to understand their behavior. Organic
compounds are molecules composed of carbon and hydrogen, and may contain any number of
other elements. The bonding in organic compounds is covalent. Many organic compounds
contain nitrogen, oxygen, halogens, and more rarely phosphorus or sulphur.

Special properties of carbon

• Carbon is unique in its almost infinite capacity of its atoms to bond to each other in long
chains. This process is known as catenation. Catenation can be defined as the self-linking
of atoms of an element to form chains and rings.

• Carbon has four valence electrons, which means that each carbon atom can form a
maximum of four bonds with other atoms. It can form stable, covalent bonds with
other atoms and appear as long chains or rings of strong interconnecting carbon-
carbon bonds. These contribute to the diversity and complexity of carbon compounds
existing on Earth.

• Because of the number of bonds that carbon can form with other atoms, organic
compounds can be very complex.

• Most organic compounds rely for their framework on carbon-carbon bonds. These
bonds between a carbon and another carbon atom can be single, double or triple
covalent bonds.

• Carbon can bond to form straight chain, branched, and cyclic molecules.

Importance of organic chemistry

Organic chemistry is the study of life and all of the chemical reactions related to life. Carbon
forms the basis of life on Earth, with millions of carbon-containing compounds making up 18
percent of all living things. Carbon is the basic building block of organic compounds that
recycles through the earth’s air, water, soil, and living organisms including human beings.

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 All life sustaining compounds (nuclei acids, proteins, enzymes, carbohydrates, lipids, vitamins
etc) are organic substances. Many useful and important compounds such as rubber, plastics,
fuel, detergents, cosmetics, dyes, etc are made from organic compounds. When combined with
biology, organic chemistry forms the basis of medical and pharmaceutical sciences. It helps us
to study, understand and discover new medicines and treatment techniques such as polio,
cancer, etc. It is an important part of biotechnology and life processes.

Representations of Organic Molecules

It is important to know all the ways in which organic compounds are represented so as to
recognise them regardless of how they are shown. There are three ways of representing
organic compounds.

Molecular Formula

The molecular formula tells us the actual number of atoms for each element that is present in a
compound. For example in the molecular formula C6 H13 OH, there are six carbon atoms,
fourteen hydrogen atoms and one oxygen atom.

Structural Formula:

A structural formula displays the atoms of the molecule in the order they are bonded. It also
depicts how the atoms are bonded to one another, for example single, double, and triple
covalent bond. Each covalent bond is represented by a line. In the diagram below, the atoms
are bonded as single bond.

Condensed Formula:

The condensed formula of a molecule is the formula where the symbols of atoms are listed in
order as they appear in the molecule's structure with bond dashes omitted or limited. A
true condensed formula can be written on a single line without any branching above or below
it. Using the diagram above, the condensed formular of the compound can be written as:

CH3 CH2 CH2 CH2 CH2 CH2 OH

Functional Group

In organic chemistry, a functional group is an atom, a specific group of atoms or bond (s) within
a compound that are responsible for the characteristic chemical reactions of that compound.

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Functional groups are important in determining how a compound will react and they are used
to distinguish similar compounds from each other.

Homologous Series

A homologous series is a group of compounds with the same general formula and contain the
same functional groups.

Hydrocarbons: these are organic compounds which contain hydrogen and carbon atoms only.
There are divided into three groups, which are:

1. Alkanes

These are hydrocarbons that contain only single bonds. The functional group of alkanes is the
single bond. Each carbon atom is bonded to four other hydrogen atoms .
Hydrocarbons that contain only single bonds are called saturated hydrocarbonsThe general
formula of alkanes is Cn H2n+2 where n is the number of carbon atoms. Ethane, C2 H6 is an
example of an alkenes and its structural formula is:

The table below shows the names and molecular formulas of the first eight alkanes:

NAME NUMBER OF CARBONS MOLECULAR FORMULA

Methane 1 CH4
Ethane 2 C2 H6
Propane 3 C3 H8
Butane 4 C4 H10
Pentane 5 C5 H12
Hexane 6 C6 H14
Heptane 7 C7 H16
Octane 8 C8 H18

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The first part of the name of an alkane (prefix) indicates the number of carbon atoms in the
compound. The last part of the name indicates that the compound belongs to a homologous
series of alkanes e.g.
• Meth-(prefix, one carbon) and the suffix – ane(an alkane), hence the name is methane
• Hex-(prefix ,six carbons) and the suffix –ane(an alkane) hence the name hexane

Alkanes are mostly used as fuels. Other common uses include electricity generation, production
of polymers, as a lubricant, paraffin wax, as an intermediate in the synthesis of drugs and
pesticides.

2. Alkenes
They have double bonds as their functional group (C=C) and hence they are referred to
as unsaturated. Hydrocarbons that are unsaturated contain double or triple bonds.
The general formula for alkenes is Cn H2n .Propene C3 H6 is an example of alkene is
shown below:

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 3. Alkynes
These have triple bonds and unsaturated. The general formula is Cn H2n−2 . Butyne
C4 H6 is shown below:

Similar to how alkanes are named, alkenes and alkynes are named with a prefix (number of
carbons) and a suffix (homologous series it belongs to)

• Eth-(prefix, two carbons) and the suffix – ene(an alkene), hence the name is ethene
• But-(prefix ,four carbons) and the suffix –yne(an alkyne) hence the name butyne

Haloalkanes

These are organic compounds that are similar to alkanes but with one or more of the hydrogen
atoms replaced by a halogen.They are also known as alkyl halides. The general formular for
haloalkanes is Cn H2n+1 X (X = F, Cl, Br, I) .The diagram below shows a general representation
the functional group of a haloalkane. R stands for the rest of the molecule.

Haloalkanes are also known as allkyhalides. 2-chlorobutane is an example of a haloalkane as

shown.

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Alcohols

An alcohol is any organic compound where there is a hydroxyl functional group (OH) bonded to
a carbon atom as shown below:

The general formula for a simple alcohol is Cn H2n+1 OH. They are named using the ending –ol,
and OH group gets the lowest number.

Alcohols are highly flammable and are mostly liquids at room temperature. Ethanol is an
example of an alcohol.

Alcohols can be classified as either primary, secondary or tertiary.

Primary alcohols: -OH (hydroxyl group) is bonded to a carbon atom that is bonded to only one
other carbon atom e.g. butan-1-ol

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Secondary alcohols: -OH group is bonded to a carbon atom that is bonded to two other carbon
atoms e.g. butan-2-ol

Tertiary alcohols: -OH group is bonded to a carbon atom that is bonded to three other carbon
atoms 2-methylpropan-2-ol

In summary they can be represented as follows:

Carboxylic Acids

Carboxylic acids are organic acids that are characterized by having a functional group known as
a carboxyl, written as COOH. The general formula for carboxylic acids is Cn H2n O2 .The
structural formula of the carboxyl is shown below. R stands for the rest of the molecule.

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The names of carboxylic acids end with the suffix –oic acids e.g. butanoic acid which is shown
below.

Esters

Esters are chemical compounds derived by reacting an alcohol with a carboxylic acid. In the
process of forming the ester, a water molecule is removed. The water comes from removing an
OH group on the carboxylic acid and combining it with a H from the alcohol. The reaction is
known as esterification.

A catalyst is required in this reaction; in this case it must be an inorganic acid (e.g. H2 SO4 ).
The formula for esters is RCOOR’ (where R and R’ are any organic combining groups)The
formula feature a carbon-to-oxygen double bond that is also singly bonded to a second oxygen
atom as shown below:

The name of an ester is a two-part name. The first part is the alkly derived from the alcohol and
the second part(separate word) ends in –anoate derived from the carboxylic acid. The general
formula for esters is Cn H2n O2 .

Esters have sweet fruity smells or fragrances. This is why some of them are used as food
flavourings and other esters are used as fragrances or perfumes or in cosmetics. Apart from
that, they can be turned into polymers known as polyesters which can be used to make cans or
plastic bottles. Polyesters can be further converted into fibres to make clothing.

The diagrams below, show the structural formulas for the formation of esters.

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Aldehydes and Ketones

These are organic compounds which incorporate a carbonyl functional group, C=O.
In aldehydes, the carbonyl group has a hydrogen atom attached to it together with either a
second hydrogen atom or more commonly a hydrocarbon group which might be an alky group.
Aldehydes names end with –al.

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Examples of aldehydes include:

Ketones contain the carbonyl group bonded between two carbon atoms. Ketones never have a
hydrogen atom attached to a carbonyl group. The names of ketones end with –one.

Examples of ketones:

Propanone 2-butanone

The general formula for aldehydes and ketones is Cn H2n O.

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Structural Isomers

Structural isomers are organic compounds with the same molecular formula but differ
structurally. Structural isomers differ with regards to the specific attachment of atoms and
functional groups. There are three types of structural isomers namely chain isomers, positional
isomers and functional isomers.

Chain Isomers

These isomers arise because of the possibility of branching in carbon chains. For example, there
are two isomers for the alkane with molecular formula C4 H10. Butane has all four carbons in a
straight or linear chain,while its isomer 2-methylpropane has three carbons in the longest chain
and a methyl group attached to the second carbon in the chain. The functional groups are the
same for both compounds (single bonds) as shown below.

Functional Isomers

Functional isomerism occurs when substances have the same molecular formula but
different functional groups. This means that functional isomers belong to different homologous
series.

Carboxylic acids and esters with the same number of carbons are functional isomers.
For example, propanoic acid and methyl ethanoate have the same formula of C3 H6 O2 . They
belong to different homologous series as shown:

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Note: Propanone and propanal are examples of functional isomers not positional isomers.

Propanal Propanone

Positional Isomers

These isomers have the same molecular formula but differ in the position of one or more
functional groups or substituted groups.

1-chloropropane and 2-chloropropane are another set of positional isomers as shown. The
halogen is on carbon number one for the one molecule and on carbon number two for the
other.

NAMING ORGANIC COMPOUNDS

The increasingly large number of organic compounds identified with each passing day, together
with the fact that many of these compounds are isomers of other compounds, requires that a
systematic nomenclature system be developed. Just as each distinct compound has a unique
molecular structure which can be designated by a structural formula, each compound must be
given a characteristic and unique name.
In chemical nomenclature, the IUPAC nomenclature of organic chemistry is a method of organic
chemical compounds as recommended by the International Union of Pure and Applied

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Chemistry (IUPAC). A good general rule to follow is to start at the end (the suffix) and work
backwards (from right to left) in the name.

1. Identify the functional group in the compound. This will determine the suffix of the
name e.g. alkanes will end with –ane, alkenes –ene, alcohols –ol as shown in the table
below:

Functional group Suffix

Alkane -ane
Alkene -ene
Alkyne -yne
Alcohol -ol
Aldehyde -al
Ketone -one
Carboxylic acid -oic acid
Ester -oate

2. Find the longest continuous carbon chain and count the number of carbons in this long
chain. This number will determine the prefix (the beginning) of the compound’s name.
This chain must include the functional group, and need not be in a straight line .The
functional group can be a double or triple bond, a hydroxyl group, a carbonyl group or a
carboxyl group. Number the carbons in the longest carbon chain, starting with the
carbon at the end closest to the functional group.

Prefix Number of carbons

Meth 1
Eth 2
Prop 3
But 4
Pent 5
Hex 6
Hept 7
Oct 8

3. In the case of alkanes or alkyl halides, start numbering from the carbon nearest to a
substituent (side chain) e.g. an alkyl group or halogen atom. If the same substituent
occurs more than once, the location of each point on which the substituent occurs must

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 be given e.g. 2,4 -. This shows that the side chain is found on carbon two and four. In
addition, the number of times the substituent group occurs is indicated by a prefix
[di (two), tri (three), tetra (four) etc ]. For halogens the names are given in short cuts,
flouro for fluorine (F), chloro for chlorine (Cl), bromo for bromine(Br) and iodo for
iodine (I).

4. Assemble the name into a single word in the following order:

• Place the position numbers and names of the branched groups/halogen atoms
in (ignoring prefixes) in alphabetical order, before the root name.
• In alphabetizing, ignore prefixes like -, di, tri, tetra etc. Always include a position
number for each substituent, regardless of redundancies.
• Add the prefix of main chain
• Name the ending according to the functional group and its position on the
longest carbon chain.

Exercise 1

Give the IUPAC name of the following compound

(a) (b)

(c) (d)

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(e) (f)

(g) (h)

(i) (j)

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(k) (l)

Draw the structural formula of the following compounds:

(a) Pent-2-ene
(b) 4,4-dimethylhexan-2-one.
(c) 2-methly-3-heptyne
(d) 2-methlypentan-1-ol
(e) 4,5-dimethly-3-heptanone
(f) 2,3-dichloro-4-ethly-hex-2-ene
(g) 4-methlyhexanoic acid
(h) 3-chloro-3-methyl-1-butyne
(i) 2-methly-propan-2-ol
(j) 2,3-dibromo-3-methylpentane

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