introduction
ORGANIC CHEMISTRY
Why Should You Study Organic
Chemistry?
What is Organic Chemistry?
The modern usage of organic chemistry
refers to the chemistry of compounds
containing carbon, but this definition should
be clarified because compounds such us
carbon monoxide, carbon dioxide and
calcium carbonate are considered to be
inorganic.
What is Organic Chemistry?
Today ORGANIC CHEMISTRY is defined as
the study of hydrocarbons (compounds of
hydrogen and carbon) and their derivatives.
About Carbon Atom
Able to form stable covalent bonds with other
carbon atom.
Can form chain, branch, cyclic compounds.
Carbon can form stable bonds with other elements
such as C, N, S,O, H.
Can form single/double/triple bonds with other
carbon atom to produce a variety of organic
compounds with different properties.
the fundamental building block of material in living
organisms and is important to many industries
History and Development
1685
Nicolas Lemery
a French chemist, published a book entitled
Course de Chyme in which he classified
substances as animal, vegetable, or mineral on
the basis of their origin. This was probably the
first attempt made to distinguish substances
derived from plant or animal sources from
those obtained from mineral constituents
1769-1785
Carl Wilhelm Scheele
A Swedish chemist isolated and characterized
a large number of chemical substances
derived from living systems. Little was known
about the chemical composition of these
substances.
Late 18th Century
Antoine Lavoisier
a French scientist developed his classic
combustion experiments. He devised a
method of burning these compounds in pure
oxygen gas and found that the combustion
products were carbon dioxide and water,
indicating that compounds contained carbon
and hydrogen.
1814
Jons Jacob Berzelius
A Swedish chemist gave the term organic
compounds to the substances which were
isolated from living organisms. He felt that
the synthesis of organic compounds was
impossible and held the belief that their
synthesis involved a “vital force” present only
in living things.
1828
Friedrich Wohler
Birth of modern organic chemistry
A German chemist who proved Berzelius
wrong when he unintentionally converted
ammonium cyanate, a pure inorganic
substance into urea., which is an end product
of animal metabolism. This discovery set the
stage for the eventual overflow of the vital
force theory.
1830
Berzelius used the term isomerism
(composed of equal parts) to describe
substances which had the same chemical
composition but very different properties.
1832
Wohler and Justus Von Liebig
Produced a series of compounds all
containing benzoyl radical, and their work
encourage others to discover new radicals by
systemic reactions of organic compounds.
1837
Jean Baptiste Dumas and August Laurent
French scientist who developed the
substitution theory. Dumas recognized that
an atom of one element may replace that of
another element in an organic compound.
Laurent generalized Dumas’s ideas, stating
that radicals replace each other by
substitution.
1839
Charles Gerhardt
Laurent’s assistant he develop the “Theory
of Residue”
He also introduced the term homologous
series to describe a series of compounds in
which members differ by multiples of the
molecular fragment containing 1 atom
carbon and 2 atoms of hydrogen.
1846
Laurent postulated that water, alcohol, ether,
potassium hydroxide and potassium oxide
were analogous compounds
1850-52
Alexander William Williamson
Verified Laurent’s idea and he showed that
the ethyl radical was present in both alcohol
and ether and that alcohol or ether could be
viewed as a water molecule in which one or
two H’s respectively, have been replaced by
an ethyl radical.
1853
Gerhaldt generalized Williamson’s statement
and formulated theory of types in which he
aid there were four inorganic types from
which all organic compounds were derived.
Water, HCl, ammonia and hydrogen.
1858
Friedrich August Kekule and Archibald Scott
Couper
Introduced the general rules of valence bonds
and the pictorial representation of a molecule
as a group of connected atoms. They
postulated that a carbon atom always has
valence of four, hydrogen and chlorine one,
oxygen two and nitrogen three.
1874
Jacobus Henricus Van’t Hoff and Joseph
Achille Le Bel
Proposed that the four bonds of carbon were
located at equal angles to each other ion
space.
1917
Lewis
Described chemical bonds as electrons pairs.
Organic and Inorganic
Compounds
Organic compounds- obtained from living
organism
Inorganic compounds- obtained from mineral
constituents of the earth.
Contrasting Properties of Organic and
Inorganic Compounds
Organic Inorganic
Low melting points High melting points
Low boiling points High boiling points
Low solubility in water, high solubility High solubility in water, low solubility
in non polar solvents in non polar solvents
Flammable Non flammable
Solutions are non-conductors of Solutions are conductors of electricity
electricity
Chemical reactions are usually low Chemical reactions are rapid
Exhibit isomerism Isomers are limited to a few exceptions
Exhibit covalent bonding Exhibit ionic bonding
Exist as gases, liquids and solids at Exist predominantly as solids at room
room temperature temperature
Hydrocarbons and Hydrocarbon
Derivatives
Hydrocarbons – compounds contains only
carbon and hydrogen atoms.
Hydrogen derivatives – compound that
contains carbon and hydrogen and one or
more additional element/s. Common
additional elements found in hydrocarbon
derivatives include O, N, S, P, F, Cl, and Br.
Classes of Hydrocarbons
Saturated hydrocarbons
- hydrocarbon in which all carbon-carbon
bonds are single bonds
- simplest type of organic compounds
Unsaturated hydrocarbons
- hydrocarbon that contains one or more
carbon-carbon multi-bonds: double bond, triple
bonds or both
Types of Hydrocarbons
Aliphatic Hydrocarbons
- hydrocarbon molecules that have their carbon atom
skeletons arranged in straight or branch chains
-example: alkanes, alkynes and their cyclic analogs
Aromatic Hydrocarbons
- compounds that contain a planar, cyclic
arrangement of carbon atoms
- organic substances whose carbon atom skeletons
are arrange in hexagonal rings, based on benzene.
Structural Characteristics of Alkanes
Alkanes – saturated hydrocarbon in which the
carbon atom arrangement is acyclic (not
cyclic)
- contains only carbon-carbon single bonds
and has no rings of carbon atoms.
- general formula:
CnH2n + 2
where n is the number of carbon atoms
present
Example
CH4
C2H6
C4H10
Structural Formulas of
Alkanes
Structural formula – indicates which atoms
in a molecule are bonded together and
whether by single , double or triple bond
Two dimensional representation of the
arrangement of the atoms in a molecule, but
does not give information about the spatial
orientation of the atom.
Types of Structural Representation of
Organic Compounds
Expanded structural formula
- shows in two dimensions, all atoms in a
molecule and all the bonds connecting them.
Example:
CH3-CH2-CH3
Propane
Condensed Structural Formula
- uses of groupings of atoms, in which central
atoms and the atoms connected to them are
written as a group, to convey molecular
structural information.
Example:
C3H8
Propane
Note:
***when written out, expanded structural
formulas generally occupy a lot of space and
condensed structural formulas represent a
shorthand method for conveying the same
information.
Skeletal Formulas
Formulas that omit hydrogen atoms
Example:
C
Structural Isomerism of
Alkanes
Structural isomerism – are compounds with
the same molecular formula but different
structural formula.
***Structural isomers with their differing
structural formulas, always have different
properties and are different compounds and are
considered as one of the major reasons for the
existence of so many organic compounds
Types of Isomers
Continuous – chain alkane
- alkane in which all carbon atoms are
connected in a continuous chain.
Example:
CH3-CH2-CH2-CH2-CH2-CH3
Hexane
Branch – Chain alkane
- alkane with one or more branches of carbon
atoms attached to a continuous chain of carbon
atoms.
Example: CH3
CH3-CH2-CH2-CH2-CH-CH3
Number of Structural Isomers Possible for
Alkanes of Various Carbon Chain Length
Molecular Formula No of Isomers
CH4 1
C2H6 1
C3H8 1
C4H10 2
C5H12 3
C6H14 5
C7H16 9
C8H18 18
C9H20 35
C10H22 75
C11H32 4, 247
C20CH42 336, 319
C30H62 4, 111, 846, 767
IUPAC Nomenclature of Alkanes
IUPAC – International Union of Pure and Applied
Chemistry
- formulated and updated periodically the naming of
organic compounds.
***the advantage of the IUPAC naming system is that
it assigns each compound a name that not only uniquely
identifies but also enables one to draw its structural
formula.
“ANE”- the characteristic ending for all alkane names.
***beginning with the five carbon alkane, Greek
numerical prefixes are used to denote the actual no. of
carbon atoms in the continuous chain.
IUPAC Names for the First Ten Continuous
Chain Alkanes
Molecular Formula IUPAC IUPAC Structural Formula
Prefix Name
CH4 Meth- Methane CH4
C2H6 Eth- Ethane CH3CH3
C3H8 Prop- Propane CH3CH2CH3
C4H10 But- Butane CH3CH2CH2CH3
C5H12 Pent- Pentane CH3CH2CH2CH2CH3
C6H14 Hex- Hexane CH3CH2CH2CH2CH2CH3
C7H16 Hep- Heptane CH3CH2CH2CH2CH2CH2CH3
C8H18 Oct- Octane CH3CH2CH2CH2CH2CH2CH2CH3
C9H20 Non- Nonane CH3CH2CH2CH2CH2CH2CH2CH2CH3
C10H22 De- Decane CH3CH2CH2CH2CH2CH2CH2CH2CH2CH3
To name branched-alkanes we must be able
to name the branch or branches that are
attached to the main chain.
Substituents- is an atom or a group of atoms
attached to a chain (or chain) of carbon
atoms.
Alkyl group- is a group of atoms that would
be obtained by removing a hydrogen atom
from an alkane.
- names of alkyl groups always ends in -yl
Example:
---CH3 CH2 CH3
methyl group ethyl group
***the extra long bond in these formulas denote
the point of attachment to the carbon chain. Note
that alkyl groups do not lead a stable, independent
existence, they are always found attached to
another entity (usually a carbon chain)
IUPAC Rules for Naming Branched-
chain Alkanes
Rule 1. Identify the longest continuous carbon
chain (parent chain), which may or may not be
shown in a straight line and name the chain.
Example:
CH3—CH2—CH2—CH—CH3
CH3
CH3—CH—CH2—CH2—CH3
CH2
CH3
**if two different carbon chains in a molecule have
the same largest no. of carbon atoms, select as the
parent chain the one with the largest no. of
substituents (alkyl group) attached o the chain.
Rule 2. Number the carbon atoms in the parent
chain from the end of the chain nearest a
substituent (alkyl group).
There are two ways to number (either from left
to right or from right to left). This rule gives the first
encountered alkyl group the lowest possible
number.
Example:
CH3—CH2—CH2—CH—CH3
CH3
right to left numbering system
CH3—CH—CH2—CH2—CH3
CH2
CH3
left to right numbering system
***additional guidelines for numbering carbon
atom chains.
1. If each end of the chain has a substituent the
same distance in, number from the end closed
to the second encountered substituent.
2. If there are substituents equidistant from each
end of the chain and there is no third
substituent to use as the “tie breaker”, begin
numbering nearest the substituent that has
alphabetical priority-that is the substituent
whose name occurs first in the alphabet.
Rule 3. If only one alkyl group is present, name and
locate it (by number) and attach the number and
name to that of the parent carbon chain
Example:
CH3—CH2—CH2—CH—CH3
CH3
2-methyl pentane
CH3—CH—CH2—CH2—CH3
CH2
CH3
3-methyl hexane
Rule 4. If two or more of the same kind of alkyl
group are present in a molecule, indicate the
number with a Greek prefix (di, tri, tetra, penta,
hexa, and so forth). In addition, a number
specifying the location of each identical group
must be included. These position numbers,
separated by commas, preceded the numerical
prefix, numbers are separated from words by
hypens.
Example:
CH3—CH—CH2—CH—CH3
CH3 CH3
2,4-dimethyl pentane
CH3
CH3—CH2—C—CH2—CH3
CH3
3,3-dimethyl pentane
Rule 5. when two kinds of alkyl groups are present
in the same carbon chain, number each group
separately, and list the names of the alkyl groups in
alphabetical order.
Example:
CH3—CH2—CH—CH—CH3
CH2 CH3
CH3
3-ethyl -2-methyl pentane
CH3—CH2—CH—CH—CH—CH2—CH2—CH3
CH2 CH2 CH2
CH2 CH2 CH3
CH3 CH3
4,6-diethyl -5-propyl nonane
Rule 6. Follow IUPAC punctuation rules, which
include the following:
1. Separate numbers from each other by
commas.
2. Separate numbers from letters by hyphens
Cycloalkanes
Is a saturated hydrocarbon in which the
carbon atoms are connected to one another
in a cyclic or ring like arrangement.
The general formula for cycloalkanes is CnH2n
The simplest cycloalkane is cyclopropane,
which contains a cyclic arrangement of three
carbon atoms
Geometrical figures are often used to
represent the cyclic portion(s) of cycloalkane
structure.
Example: cyclopropane, cyclobutane,
cyclopentane, cyclohexane.
IUPAC Nomenclature For Cycloalkanes
IUPAC naming procedure for cycloalkanes are
similar those for alkanes. The ring portion of a
cycloalkane molecule serves a the name base
and the prefix cyclo is used to indicate the
presence of the ring
Numbering conventions used in locating
substituents include the ff:
1. If there is just one ring substituent, it is not
necessary to locate it by number.
2. When two ring substituents are present, the
carbon atoms in the ring are numbered by
beginning with the substituent of higher
alphabetical priority and proceeding in the
direction (clockwise or counterclockwise) that
gives the other substituent the lowest number
possible.
When three or more substituents are present,
ring numbering begins at the substituent that
leads to the lowest set of location numbers.
When two or more equivalent numbering sets
exists, alphabetical priority among
substituents determine the set used.
Isomerism in Cycloalkanes
Structural isomerism are possible for
cycloalkanes that contain four or more
carbon atoms.
There are five cycloalkane structural isomers
that have the formula C5H10
Cis-Trans Isomers
Are compounds that have the same
molecular and structural formulas but
different arrangements of atoms in space
because of restricted rotation around bonds.
In alkanes, there is free rotation about all c-c
bonds. In cycloalkanes, the ring structure
restricts rotation for the carbon atoms in the
ring. The consequence of this is lack of rotation
in a cycloalkane for the creation of top and
bottom positions for the two attachments on
each of the ring carbon atoms. This top-bottom
situation may lead to cis-trans isomerism in
cycloalkanes with two or more substituents on
the ring.
Example: for the molecule 1,2-
dimethylcyclopentane
Cis- 1,2- dimethylcyclopentane
Trans-1,2- dimethylcyclopentane
The latin cis- means on the same side and the
latin trans- means across.
A cis isomer is an isomer in which two atoms
or groups are on the same side of a restricted
rotation barrier in a molecule.
A trans isomer is an isomer in which two
atoms or groups are on different sides of a
restricted rotation barrier in a molecule.
Some Classes of Organic Compounds
by Functional Group
Simple Aliphatic Nomenclature
