Organic

Chemistry
 THE
NATURE OF ORGANIC
CHEMISTRY
 ORGANIC CHEMISTRY
is the study of the
properties of the
compounds of carbon
that are organic. All
carbon compounds
except for a few
inorganic carbon
compounds are organic.
 The name organic
chemistry came from
the word ORGANISM.
Prior to 1828, all
organic compounds
had been obtained
from organisms or
their remains.
 JÖNS JACOB BERZELIUS

A physician by trade, first coined the term “ORGANIC

CHEMISTRY” in 1807 for the study of compounds derived from
biological sources.
 Up through the early 19th
century, naturalists and
scientists observed critical
differences between
compounds that were derived
from living things and those
that were not.
 The belief then was that the
synthesis of organic compounds from
inorganic compounds in the laboratory
was impossible.
 Inorganic carbon compounds
include the oxides of carbon, the
bicarbonates and carbonates of
metal ions, the metal cyanides, and
a few others.
 There are over six million
organic compounds
characterized, including the
foods we eat, (made of
carbohydrates, lipids,
proteins and vitamins), furs
& feathers, hides & skins &
the organisms they came
from.
Not to mention plastics, synthetic and natural fibers, dyes

and drugs, insecticides and herbicides, ingredients in

perfumes and flavoring agents, and petroleum products.

 Chemists during those period noted that
there seemed to be an essential yet
inexplicable difference between the
properties of the two different types of
compounds.
 The vital force theory (sometimes called
"vitalism") was therefore proposed (and
widely accepted) as a way to explain these
differences.
 VITALISM proposed that there was
something called a "vital force" which
existed within organic material but did
not exist in any inorganic materials.
All efforts had failed and scientists
became convinced that some "vital
force" that living organisms had was
necessary to make an organic
compound.
As an example is the synthesis of UREA from
inorganic substances in 1828 led to the
disappearance of this vital force theory.
Organic chemistry defines life. Just as
there are millions of different types of
living organisms on this planet, there
are millions of different
organic molecules, each with different
chemical and physical properties.
 There are organic chemicals
that make up your hair, your skin,
your fingernails, and so on. The
diversity of organic chemicals is due
to the versatility of the carbon atom.
 WHY IS CARBON SUCH A SPECIAL
ELEMENT?

Carbon (C) appears in the second row of the

periodic table and has 4 bonding electrons in
its valence shell.
 Carbon therefore forms four bonds
with other atoms(each bond consisting
of one of carbon's electrons and one of
the bonding atom's electrons).

Carbon forms 4 bonds

 Every valence
electron participates
in bonding, thus a
carbon atom's bonds
will be distributed
evenly over the
atom's surface.
These bonds form a
tetrahedron (a
pyramid with a spike
at the top), as
illustrated:
 The simplest organic chemicals,
called hydrocarbons, contain only
carbon and hydrogen atoms.
The simplest hydrocarbon (called
METHANE) contains a single carbon
atom bonded to four hydrogen atoms:

METHANE – a carbon atom

bonded to 4 hydrogen atoms
But carbon can bond to other
carbon atoms in addition to hydrogen,
as illustrated in the molecule ETHANE:

ETHANE - a carbon-carbon
bond
 In fact, the uniqueness of carbon
comes from the fact that it can bond to
itself in many different ways.
Carbon atoms can form long chains:

HEXANE - a 6-carbon
chain
branched chains:

ISOHEXANE - a branched-
carbon chain
 rings:

CYCLOHEXANE
- a ringed hydrocarbon
There appears to be almost no limit to
the number of different structures that
carbon can form.
 To add to the complexity of organic
chemistry, neighboring
carbon atoms can form double and
triple bonds in addition to single
carbon-carbon bond.
 Keep in mind that each
carbon atom forms FOUR BONDS. As
the number of bonds between any two
carbon atoms , the number of
hydrogen atoms in the molecule :

Single Double Triple

bonding bonding bonding
 Why is Organic Chemistry
IMPORTANT?

It is important because it is the

study of LIFE and all of the chemical
reactions related to life.
 Several careers apply an understanding of organic
chemistry, such as doctors, veterinarians, dentists,
pharmacologists, chemical engineers, and chemists.
 Organic chemistry plays a part in the
development of common household
chemicals, foods, plastics, drugs, fuels...
really most of the chemicals part of daily life.
CLASSIFICATION OF ORGANIC
COMPOUNDS

1)FUNCTIONAL
GROUPS
HYDROCARBONS contain only C & H.
In addition to carbon and
hydrogen, hydrocarbons can also
contain other elements. Hydrogens in
hydrocarbons can be replaced by
other atoms or groups of atoms.
These replacements, called functional
groups are the reactive sites in
molecules. In fact, many common
groups of atoms can occur within
organic molecules, these groups of
atoms are called functional groups.
One good example is
the hydroxyl functional group.
Hydroxyl FUNCTIONAL GROUP
The HYDROXYL GROUP
consists of a single oxygen
atom bound to a single
hydrogen atom (-OH). The
group of hydrocarbons that
contain a hydroxyl functional
group is called alcohols. The
alcohols are named in a
similar fashion to the simple
hydrocarbons, a prefix is
attached to a root ending (in
this case "anol") that
designates the alcohol.
 hydroxyl functional
group
The family of carboxylic acids contains a
carboxyl (-COOH) functional group. Acetic
acid is an example.
ETHANOL, common drinking alcohol, is
the active ingredient in "alcoholic"
beverages
such as beer and wine.
 The concept of functional groups
is central in organic chemistry, both
as a means to classify structures and
for predicting properties. A functional
group is a molecular module, and the
reactivity of that functional group is
assumed, within limits, to be the
same in a variety of molecules.
 Functional groups can have decisive
influence on the chemical and physical
properties of organic compounds.
Molecules are classified on the basis of
their functional groups.
 Alcohols, for example, all
have the subunit C-O-H. All
alcohols tend to be
somewhat hydrophilic,
usually form esters, and
usually can be converted to
the corresponding halides.
Most functional groups

feature hetero atoms

(atoms other than C and H).
 The atom that is not carbon is called
the heteroatom. The heteroatom's
bonds must be shown or clearly
understood. For example, nitrogen
normally forms three bonds, so three
bonds must be indicated for it. Oxygen
normally forms two, so two bonds must
be shown. Rings may have more than
one heteroatom.
 In organic chemistry, there are a few basic
structural shapes that you will encounter. They

are chains and rings.

There are also two types of chains, a straight
chain, and a branched chain. In a straight chain,
one carbon atom holds no more than two other
carbon atoms. As its name implies, the straight
chain is a straight link of carbon, sometimes
oxygen or nitrogen, atoms, in structural formula
that is. Because of twisting and contouring, they
chain may have several conformations .
 Branched chains have at least one carbon holding
more than two other carbon atoms. It will, as its
name implies, have branches of other chains coming
off another chain. have at least one carbon holding
more than two other carbon atoms. It will, as its
name implies, have branches of other chains
H coming
|
off another chain. Branching is
H
one of the reasons
H H H-C-H H H H
why there are so many isomers |
for each
| | |
compound.
| | |
H---C---C-C---C---C-C-C-H
| | | | | | |
H H H H H H H-C-H H H H H H H
| | | | | | |
H-C-C-C-C-C-C-H H-C-H
| | | | | | |
H H H H H H H
Straight Chain Branched Chain
Rings (or cyclic compounds) are composed of rings
of carbon and sometimes oxygen or nitrogen. For
example, cyclohexane has a ring of six carbon
atoms.

A cyclohexane molecule in CHAIRCONFORMATION.

Hydrogen atoms in axial positions are shown in red,
while those in equatorial positions are in blue.
ETHYNE
ACETYLENE

ISOBUTANE
The hydroxyl group consists of a single
oxygen atom bound to a single
hydrogen atom (-OH). The group of
hydrocarbons that contain a hydroxyl
functional group is called alcohols.
The alcohols are named in a similar
fashion to the simple hydrocarbons; a
prefix is attached to a root ending (in
this case "anol") that designates the
alcohol.
The existence of the functional group
completely changes the chemical
properties of the molecule. Ethane, the
two-carbon alkane, is a gas at room
temperature; ethanol, the two-carbon
alcohol, is a liquid. Double & triple
bonds are considered to be functional
groups.
 Some common functional groups are:
ALKANE(single bond), ALKENE(2 bond),
ALKYNE(3), ALCOHOL(has h), KETONE,
ALDEHYDE, CARBOXYLIC ACID, ESTER,
AMIDE & NITRILE. The "R" group is a
generic group, and is not a part of the
functional group of interest.
 Compounds with the same functional
group form a homologous series having
similar chemical properties and often
exhibiting a regular gradation in
physical properties with increasing
molecular weight.
2) Aliphatic compounds
 The aliphatic hydrocarbons are
subdivided into three groups
of HOMOLOGOUS SERIES according to
their state of SATURATION:

>Where n represents the number of

carbon atoms present.

>HOMOLOGOUS GENERAL FUNCTIONAL
EXAMPLE
SERIES FORMULA GROUP
Straight
CnH2n + 2 (n ≥ 1) CH4, n = 1
Chain Alkanes
Alkyl CnH2n + 1 (n ≥ 1) CH3, n = 1
Alkenes and
CnH2n (n ≥ 2) C2H4, n = 2 C=C
Cyclic Alkanes
Alkynes CnH2n − 2 (n ≥ 2) C2H2, n = 2 C≡C

CnH(2n + 1)OH
Alcohols CH3OH, n =1 - OH
(n ≥ 1)

Carboxylic
CnH2n+1COOH CH2O2, n = 0 - COOH
acids
(n ≥ 0)

Carbohydrates Cn (H2O)n (n ≥ 1) C6H12O6

 Examples also of Aliphatic
Compounds are:

•paraffins, which are alkanes WITHOUT

any double or triple bonds,
•olefins or alkenes WHICH CONTAINS
one or more double bonds, i.e di-olefins
(dienes) or poly-olefins.
•alkynes, WHICH HAS one or more triple
bonds.
 The rest of the group is classed
according to the functional groups
present. Such compounds can be
"straight-chain," branched-chain or
cyclic.
Both saturated (alicyclic compounds)
and unsaturated compounds exist as
cyclic derivatives. The most stable
rings contain five or six carbon atoms,
but large rings (macrocycles) and
smaller rings are common.
The smallest cycloalkane family is the

three-membered cyclopropane (CH2)3

Saturated cyclic compounds contain

single bonds only, whereas aromatic

rings have an alternating (or

conjugated) double bond.

To illustrate the rules, here are some
types of cyclic compounds:

cyclopropane cyclobutane cyclopentane cyclohexane

cyclohexene
Bromocyclohexane

IUPAC NAME
Cycloalkanes do not contain multiple
bonds, whereas the cycloalkenes and
the cycloalkynes do.
3) Aromatic Compounds
 Aromatic hydrocarbons
contain conjugated double bonds. The
most important example is benzene, the
structure of which was formulated by
Kekulé who first proposed
the delocalization or resonance
principle for explaining its structure.
 Benzene

> is one of the best-known aromatic compounds

as it is one of the simplest and most stable
aromatics.
4) Heterocyclic
compounds
 The ring is termed a heterocycle.
Pyridine and furan are examples of
aromatic heterocycles
while piperidine and tetrahydrofuran
are the corresponding alicyclic
heterocycles.
 The heteroatom of heterocyclic
molecules is generally oxygen, sulfur, or
nitrogen, with the latter being
particularly common in biochemical
systems.
 Examples of groups among the
heterocyclic are the aniline dyes, the
great majority of the compounds
discussed in biochemistry such as
alkaloids, many compounds related to
vitamins, steroids, nucleic acids (e.g.
DNA, RNA) and also numerous
medicines.
 Heterocyclic with relatively simple
structures are pyrrole (5-membered)
and indole (6-membered carbon ring).
Rings can fuse with other rings on an
edge to give polycyclic compounds.
The purine nucleoside bases are
notable polycyclic aromatic
heterocycles.
Rings can also fuse on a "corner" such
that one atom (almost always carbon)
has two bonds going to one ring and
two to another. Such compounds are
termed spiro and are important in a
number of natural products.

Pyridine Furan Tetrahydrofuran

A simple
A 5 ring IUPAC NAME:
heterocyclic heteroatom OXACYCLOPENTANE
compound
5) Polymers
 One important property of carbon is
that it readily forms chain or even
networks linked by carbon-carbon
bonds. The linking process is called
POLYMERIZATION, of the chains or
networks polymers, while the source
compound is a MONOMER. An example
of a polymer that is made up or of a
polystyrene is a swimming board.
 Two main groups of polymers exist:
those artificially manufactured are
referred to as industrial polymers or
synthetic polymers and those naturally
occurring as biopolymers.
Since the invention of the first artificial
polymer, bakelite, the family has
quickly grown with the invention of
others.
 Common synthetic organic polymers
are polyethylene (polythene),
polypropylene, nylon, teflon,
polystyrene, polyesters, polymethyl
methacrylate (called perspex and
plexiglas) and polyvinylchloride (PVC).
Both synthetic and natural rubbers are
polymer.
Natural polymers (from the Greek poly
meaning “many” and meros meaning
“parts”) are found in many forms such
as horns of animals, tortoise shell,
shellac (from the lac beetle), rosin
(from pine trees), asphalt, and tar from
distillation of organic materials.
 One of the most useful of the natural
polymers was rubber, obtained from the
sap of the hevea tree. (Rubber was
named by the chemist Joseph Priestley
who found that a piece of solidified
latex gum was good for rubbing out
pencil marks on paper.
In Great Britain, erasers are still called
“rubbers”.) Natural rubber had only
limited use as it became brittle in the
cold and melted when warmed.
In 1839, Charles Goodyear discovered,
through a lucky accident, that by
heating the latex with sulfur, the
properties were changed making the
rubber more flexible and temperature
stable. That process became known as
vulcanization.
The first synthetic polymer, a phenol-formaldehyde
polymer, was introduced under the name “Bakelite”,
by Leo Baekeland in 1909. Its original use was to
make billiard balls. Rayon, the first synthetic fiber

was developed as a replacement for silk in 1911.

 CH3
CH2=C-CH=CH2
2-methyl-1, 3-butadiene
Natural rubber is a polymer of isoprene

Since latex will solidify in air, a

stabilizer is added to prevent
polymerization if the latex is to be
stored or shipped in liquid form.
>The repeating unit of the polymer

Polypropylene
6) Biomolecules
 Maitotoxin
a complex organic biological
toxin
BIOMOLECULAR CHEMISTRY is a major
category within organic chemistry
which is frequently studied by
biochemists. Many complex multi-
functional group molecules are
important in living organisms.
 Some are long-chain biopolymers, and
these include peptides, DNA, RNA and
the polysaccharides such as starches in
animals and celluloses in plants.
 The other main classes are amino
acids (monomer building blocks of
peptides and
proteins), carbohydrates (which
includes the polysaccharides),
the nucleic acids (which include DNA
and RNA as polymers), and the lipids.
 In addition, animal biochemistry
contains many small molecule
intermediates which assist in energy
production through the Krebs cycle,
and produces isoprene, the most
common hydrocarbon in animals.
 Isoprenes in animals form the
important steroid structural
(cholesterol) and steroid hormone
compounds; and in plants
form terpenes, terpenoids,
some alkaloids, and a unique set of
hydrocarbons called biopolymer
polyisoprenoids present in latex sap,
which is the basis for making rubber.
 7) Peptide Synthesis
8) Oligonucleotide Synthesis
9) Carbohydrate Synthesis
Comparison between
Organic and Inorganic
Compounds
 ORGANIC INORGANIC
COMPOUNDS COMPOUNDS

*Organic compounds *Inorganic compounds do

contain carbon. *Organic not contain carbon.
Compounds are Inorganic Compounds are
composed of few composed of all the
elements only.C, known elements.
H,O,N,S,P and halogens
are the most common.

*Organic compounds * Inorganic compounds

contain carbon- do not have carbon-
hydrogen bonds. hydrogen bonds.
 ORGANIC INORGANIC
COMPOUNDS COMPOUNDS
*They are generally found *They are generally
in living matter, i.e., obtained from non-living
animals and plants & matter, i.e., minerals.
therefore produced by Produced by non-living
living things. natural processes or by
human intervention in the
laboratory.
*Chemical reactions *Chemical reactions
are molecular and are ionic and fast. The
slow. The yields are yields are quantitative
poor due to side and there is no side
reactions. reaction.
 ORGANIC INORGANIC
COMPOUNDS COMPOUNDS
*They are usually gases, *They are usually solids
liquids or solids having having high melting and
low melting points. boiling points.

*Organic compds *Inorganic compounds

cannot form salts. can form salts. These,
These, being covalent being electrovalent
compounds, are compounds, are
generally insoluble in generally soluble in
water and other polar water and other polar
solvents. These are solvents. However,
fairly soluble in non- these are insoluble in
polar solvents. non-polar solvents.
 ORGANIC INORGANIC
COMPOUNDS COMPOUNDS
*They exhibit the *The co-ordination
phenomenon of compounds show the
isomerism. phenomenon of
isomerism only.
*They have been classified *Homologous series are
into many classes on the not found. The
basis of functional groups. compounds are mainly
Each class is represented divided as acids, bases
by a general formula and and salts.
the members show similar
properties. Each class is
known as homologous
series.
 ORGANIC INORGANIC
COMPOUNDS COMPOUNDS
*Some compounds are *Inorganic compounds
highly complex and are less complex.
have high molecular Comparatively a
masses. These complex compound is
complex compounds generally less stable.
are stable.

* Organic compounds * Inorganic compounds

does not contain metal contain metal atoms.
atoms.
 In general, if a compound contains
carbon it is organic. The reason for this
is that carbon is considered to be the
building block of life, and inorganic
compounds are said to be more mineral
than biological.
 There are, however, a few cases of
carbon-containing compounds which
are considered inorganic because of
convention, some being carbonates,
simple oxides of carbon, cyanides and
the allotropes of carbon.
 ISOMERISM - is the phenomenon
whereby certain compounds, with the
same molecular formula, exist in
different forms owing to their different
organizations of atoms.
 The concept of isomerism illustrates
the fundamental importance of
molecular structure and shape in
organic chemistry. Isomers are
molecules that have the same chemical
formula but different structural
formulas.
 CH3
I
CH3 CH2 CH CH2 CH3

CH3CH2 CH2 CH2 CH2CH3

or C6H14 or hexane