Introduction to Organic Chemistry

Introduction to Organic chemistry

1.1 Chemistry of carbon

1.2 Types of organic compound
1.3 Applications of organic compound
 INTRODUCTION TO ORGANIC
CHEMISTRY
Organic chemistry is a chemistry of carbon compounds.
Example : methane, DNA, urea, DDT (insecticide),
penicillin , nicotine, aspirin etc..

But not all carbon compounds are organics. Example :

carbonate (CO32-; cyanide (CN-), bicarbonate (HCO3-),

carbon dioxide and carbon monoxide.
 Organic chemistry is the study of compounds that contain carbon. It
is one of the major branches of chemistry.

The history of organic chemistry can be traced back to ancient times

when medicine for human extracted from plants and animals to treat
members of their tribes.

In ancient era, it was produced willow bark which was used as a pain
killer, (willow bark contains acetylsalicylic acid, the ingredient in
aspirin )- Organic Chemistry.

Organic chemistry was first defined as a branch of modern science in

the early 1800's by Jon Jacob Berzelius. He classified chemical
compounds into two main groups:

i. Organic: if they originated in living or once-living matter, and

ii). Inorganic: if they came from "mineral" or non-living matter.

In 1828, Frederich Wöhler discovered that urea - an organic compound - could be

made by heating ammonium cyanate (an inorganic compound).
Wöhler mixed silver cyanate and ammonium chloride to produce solid silver chloride
and aqueous ammonium cyanate:

He then separated the mixture by filtration and tried to purify the aqueous
ammonium cyanate by evaporating the water.
Chemistry of Carbon
 The carbon family, Group 14 in the p-block, contains carbon (C), silicon (Si),
germanium (Ge), tin (Sn), lead (Pb), and flerovium (Fl). Each of these elements has
only two electrons in its outermost p orbital: each has the electron configuration
ns2np2.

 Catenation is the linkage of atoms of the same element into longer chains.
 Catenation occurs most readily in carbon, which forms covalent bonds with other
carbon atoms to form longer chains and structures.
 Catenation is the reason for the presence of the vast number of organic compounds
in nature.
 WHY ORGANIC CHEMISTRY SPECIAL?

1. Carbon-carbon bonds are strong, long chains or rings of carbon atoms bonded to one another are possible.

2. Diamond and graphite are two familiar examples: a. Diamond lattice being a three-dimensional network
of carbon atoms, b. Graphite more closely resembles a planar network.

3.Carbon is not unique in forming bonds to itself because other elements such as boron, silicon, and
phosphorus form strong bonds in the elementary state. But with the combination of hydrogen carbon affords a
remarkable variety of carbon hydrides (Hydrocarbons)

4. Carbon forms bonds not only with itself and with hydrogen but also with many other elements, including
strongly electron-attracting elements
 TYPES OF ORGANIC COMPOUNDS
Organic compound: An organic compound is any member of a large
class of gaseous, liquid, or solid chemical compounds
whose molecules contain carbon. Such as carbides, carbonates,
simple oxides of carbon (such as CO and CO2), etc.
 SOURCES OF ORGANIC COMPOUNDS

There are three generally accepted sources of organic compounds :

1. carbonized organic matter:

o Carbonization is the term for the conversion of an organic
substance into carbon or a carbon-containing residue
through pyrolysis or destructive distillation.
o Example: the generation of coal gas and coal tar from
raw coal. Fossil fuels from vegetable matter, coal to
produce coke. the charcoal making process, etc.

2. Living organisms
oThe chemical compounds of living things are known as organic compounds because of their association
with organisms and because they are carbon-containing compounds.
oAmong the numerous types of organic compounds, four major categories are found in all living things:
carbohydrates, lipids, proteins, and nucleic acids

3. Invention/Human ingenuity
oAntibiotics, aspirin, vanilla flavoring, and heart drugs are examples of substances that no longer have to be
obtained directly from nature, they are manufactured in laboratories from organic starting materials.
oEach year over 250,000 new chemical compounds are discovered and many of these are products of
scientists' imaginations, exploration.
o Plastics are excellent examples of substances that are the product of invention - they are not found
anywhere in nature.
 Properties of typical organic and inorganic compound

Inorganic
Property Organic compound
compound
Bonding with
Usually covalent Often ionic
molecule
Forces between Generally weak Quite strong
molecules (Intermolecular force) (Electrostatic force)
Normal physical Gases, liquids or low- Usually high-
state melting-point solids melting-point solids
Usually non-
Flammability Often flammable
flammable
Solubility in water Insoluble Soluble
Conductivity Non-conductor Conductor
Rate of chemical
Slow and complex Fast and simple
reaction
 Naturally Occurred Organic Compounds
Name Of Organic Origin Usage
Compounds
Proteins From animals a) As a structural materials
Example : b) As a biological catalyst
a) Enzymes and regulators
b) Hormones
Fats and Oils From animals and To store energy
Example : vegetables
a) Triglyceride
b) Paraffin Oils
c) Almond Oils
Vitamins From food For healthy growth and
Example : functioning
A, B Complex, C, D,
E and K
 Synthetic Organic Compounds

Items Examples Usage

Plastics Poly (ethene), For packaging, plastic

Perspex. bags, as a substitute for
glass.
Medicines Tranquilizer, To treat tropical diseases
and Analgesic and such as Trypanosomiasis or
Drugs Bactericide. Sleeping Illness and
Malaria.
Pesticides Dichlorodiphenyl To kill houseflies and
trichloroethane other insects.
( DDT )
Dyes Methylene blue Give colour to the material.
 Type of organic compound
lic organic compound.docx

yclic organic compound.docx

Saturated

Unsaturated

c-aromatic organic compound.docx

-aromatic organic compound.docx

 Aliphatic Aromatic
● OPEN chains of Carbon atoms. ● CLOSE rings of Carbon atoms.
● Unbranched or Branched ● Contain a benzene ring.
● Contain Single, Double or Triple bonds.
Example: ethane (CH3–CH3)
Example: Benzene H
ethene / ethylene (CH2=CH2) H H
ethyne / acetylene ( HC CH
)
Alicyclic H H
● CLOSE rings of Carbon Atoms.
● Rings form the shape of POLYGON (triangle, square, H
rectangle or etc).
Example: Epoxide
C C
O
 Functional Groups
Functional groups: an atom or group of atoms which determine
the chemical and physical properties of an organic compound.

IMPORTANCE
 HOMOLOGOUS SERIES

All the member of a particular homologous series have:

1. Same general formula eg : CnH2n+1OH

2. Same functional group : same chemical reactions.

Eg : all alcohols contain –OH group.

3. Each member differs from the next member by a

constant –CH2.

4. As the molecular size increase, the boiling points

increase.
Alkane Nomenclature
Formula of organic compounds

Organic compounds can be complex

A system is needed that shows structure.
 We want something that is easy to read.

● Molecular formula
● Empirical formula
● Structural formula
● Condensed formula
● Bond-line formula
Molecular formula :
Actual number of atoms of each element in a molecule.
Empirical formula
Simplest ratio number of atoms of each element in a molecule.
C6H12O6 CH2O
Example: Glucose, C6H12O6
Molecular formula Empirical formula

Structural Formula:
Shows all atoms in the bonds, Bonds are
represented as line

Condensed Formula:
Shorthand way of writing Molecular formula

Bond-line formula
Represent structure between carbon-carbon bonds.
Atoms other than carbon and hydrogen are called heteroatoms.

CH3CH2CH2CH3 is shown as

CH3CH2CH2CH2OH is shown as
 Classification of isomers
Isomers
Isomers

Structural
Structuralisomers
isomers Stereoisomers
Stereoisomers

Isomers are different compounds that have the

same molecular formula.
Structural isomers

C5H12

n-pentane 2-methylbutane

2,2-dimethylpropane
Example C6H14

CH3CH2CH2CH2CH2CH3
n-hexane

(CH3CH2)2CHCH3
2-Methylpentane (CH3CH2)2CHCH3
3-Methylpentane

(CH3)3CCH2CH3 (CH3)2CHCH(CH3)2
2,2-Dimethylbutane 2,3-Dimethylbutane
 Stereoisomer
Compound with the same molecular formula and
structural formula but with different arrangement of
their bond in space.

cis-2-butene trans-2-butene

H3C CH3 H3C H

C C C C

H H H CH3
cis (large groups trans (large groups
on same side) on opposite sides)
 Naming of organic compound according to IUPAC system
1 Identify the longest carbon chain. This chain is called the parent chain

2 Identify all of the substituents (groups appending from the parent chain).

3 Number the carbons of the parent chain from the end that gives the substituents the lowest numbers.
When comparing a series of numbers, the series that is the "lowest" is the one which contains the
lowest number at the occasion of the first difference. If two or more side chains are in equivalent
positions, assign the lowest number to the one which will come first in the name.

4 If the same substituent occurs more than once, the location of each point on which the substituent
occurs is given. In addition, the number of times the substituent group occurs is indicated by a prefix
(di, tri, tetra, etc.).

5 If there are two or more different substituents they are listed in alphabetical order using the base name
(ignore the prefixes). The only prefix which is used when putting the substituents in alphabetical order
is iso as in isopropyl or isobutyl. The prefixes sec- and tert- are not used in determining alphabetical
order except when compared with each other.

6 If chains of equal length are competing for selection as the parent chain, then the choice goes in series
to:
A. the chain which has the greatest number of side chains.
B. the chain whose substituents have the lowest- numbers.
C. the chain having the greatest number of carbon atoms in the smaller side chain.
D. the chain having the least branched side chains.

7 A cyclic (ring) hydrocarbon is designated by the prefix cyclo-which appears directly in front of the base
name.
EXAMPLE

prefix Length of
Carbon
Meth 1

Eth 2

Prop 3

But 4

Pent 5

Hex 6

Hept 7

Oct 8

Non 9
1. Longest chain is 6 - hexane
Dec 10 2. Two methyl groups - dimethyl
3. Use 2,5-dimethylhexane
 Types of Organic Reactions

General

Addition Substitution Elimination Rearrangement

Specific

Hydrogenation Esterification Oxidation Hydrolysis

Addition: Two substances react together to form a single substance.

Ethane Bromoethane

Substitution (SN2 reaction): An atom or a group (leaving group) in a

molecule is replaced by another atom or group (nucleophile / electrophile).
Elimination: Removal of atoms or groups of atoms from
a saturated molecule to form an unsaturated molecule.

Rearrangement: Migration of an atom, a group of atoms or a

bond from one atom to another within molecule to form its
isomer.
 Hydrogenation
•Addition of hydrogen to a multiple bond to form a
single bond substance.

Hydrogenation of alkane

H H H
H
Pt
C C + H—H H C C H

H Hydrogen
H H H
Ethylene Ethane
 Esterification: Acid-catalyzed ester formation between alcohol and
carboxylic acid.
O Fischer esterification O
H2SO4
CH3COH + CH3CH2OH CH3COCH2CH3 + H2O
reflux
noic acid Ethanol Ethyl ethanoate

Oxidation: An increase in the number of bonds between carbon and

oxygen and/or a decrease in the number of carbon-hydrogen bonds.
 Hydrolysis
•Chemical process in which a molecule is split into
two parts by the addition of a molecule of water.

(CH3)3C–Br + H2O (CH3)3C–OH + HBr

tert-Butyl bromide tert-Butyl alcohol Hydrogen

bromide
Applications of Organic Compounds